Take Me on a Sea Cruise

Story Info
He dresses for a show.
2.7k words
4.19
42k
9
4
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
maninconn
maninconn
2,103 Followers

The doors to the auditorium opened with a ruckus, and eight women came running out wild eyed, and with a definite urgency to their purpose. The couple closest to my wife and I came running my way, with one of them exclaiming "There's one!"

They grabbed me by the elbows, looked at my wife and said "We need to borrow him for an hour or so. Don't worry it's for the floor show. It's all in good fun, and you can see what's going on if you come and watch.

We had taken this cruise with the in-laws. My wife's parents and my Sister in law's family were all together for a relaxing week in the Carribean. Being "kidnapped" like this wasn't quite as relaxing as I had planned, but everyone had been recommending you would enjoy your time by letting your hair down, getting to know your fellow passengers, and having fun exploring new adventures. So I shrugged at my wife, and went along with it.

There I was, standing on the "stage" with 3 other men in the same predicament, kidnapped by rogue teams of 2 women each. My teammates were bubbling with excitement. One was taller than the other, with long and lean legs and a cute curly haircut that framed a pretty face nicely. The other was shorter, a bit on the heavy side, quite buxom and had that jovial sparkle in her eye that you see in those people who always get a kick out of any situation, and are just fun to be around.

"Okaaaaaay!!!" exclaimed the MC. "We have our 4 teams, all complete. Now they find out their challenge!!! Your task is to take these men away, and bring them back dressed as women. The audience will vote for the best dressed man...er....woman, and the winning team members will each get a gift certificate to use in the ships stores."

My mind began to race. I could see my wife in the front row laughing hysterically. She later told me my face flushed when he said this. The other guys must've reacted in similar fashion, because several reactions around the hall were similar to my wife's, hysterical laughter as they pointed to their soon-to-be-dressed men. They guy on the end looked to the door, then waved off the MC, and left the stage to the jeering of the crowd and the dismay of his teammates. The guy next inline was a big burly guy, with a thick black moustache, shaved though dark whiskers on his chin, and a tattoo on his left bicep. I looked his way, and began to think "I can beat that guy." The guy next to me would be tough to beat though. MY 6'2'' frame innately looked more manly than his small svelte 5'7''.

"You have one hour, starting NOW!!!!" bellowed the MC. "

With each elbow firmly in the rasp of my teammates, I was ushered to their stateroom. On the way out, my wife whispered to me "This is so funny, and a little bit sexy too. I'm going to be laughing my ass off when you come back, and then fucking your ass off later tonight after we get the pictures back. Whatever those two girls do to you, I want a detailed description later." She kissed me and off we went.

"Where do we start?"

"I have an evening gown that would fit him, and wouldn't show his clothes underneath."

"Oh no, his shirt and short will show, they have to go. Take your shirt and pants off!"

I obliged, but felt a little odd their in my briefs. As they eyed me up and down, I was very self conscious, but it was exciting too. Dresses and accessories began to emerge from the girls own supplies, and I could feel stirrings down below where my belt used to be.

"We'll need something longer to cover his hairy legs, or else we'll have to shave him."

"We could use dark stockings."

"No it would show. Can we shave your legs?"

I shook my head no.

"Please, it would be so authentic, and with that other guy we need to pull out the stops"

"You can't say that to him while he is standing there in those briefs, they look too athletic and manly." She paused. "You really are a sexy man. I'm not sure now we have a chance, but you look hot standing there like that."

"She's right. If you are going to pass as a woman, you have to feel like one. You are going to shave your legs, and you will also wear dark stockings,....and panties."

I just stared at her. It was the Brenda, the larger buxom one who made up their collective mind how this was playing out. She met my gaze with that twinkle in her eye. She intended to go all out on this, and was declaring that we were all in it with her.

I thought it through, out loud. "So for a piddly $100 apiece, which we can only spend on this ship, my legs will be smooth and silky for all my friends to chuckle at in the gym, you two get to have the time of your lives molding me into a woman worthy of your clothes, even your most delicate intimates, I'll be paraded as a freak show through the lounges, lobby and casino before we get back to the theatre, where a couple hundred voyeurs will pick up the mantle of "freak witnesses," photographs will be snapped by the camera crew for everyone to ogle in the photo shop, my family will be pointing fingers and laughing as hysterically as my wife did in the intro...."

"...and you get to wear these." It was Lisa, the thin long legged one this time. She unzipped her shorts and let them fall to the floor. Those legs just didn't quit rose sleekly from the floor and terminated at the brilliant white if a shimmering silky thong. "What do you think of that?"

I tried to keep it together, but my dick shot up as she tuned to show how the thong, soon to be mine, appeared from her crotch and curved gracefully up to the top of the hips. She giggled as my briefs tented around it and said "Ok, so you like it." Another big twitch, another giggle "A lot."

The short buxom one reached for it and gently massaged me through my briefs. "Yes, I want it all." Did that come out of my mouth? She kissed my dick through the fabric, and then they both went to the bathroom to get the tools of their trade. When they returned, they laid a towel on the bed, and Brenda began shaving my legs, while Lisa painted my toes a brilliant red. I think I stopped breathing as their gentle cool touched attended to me. Brenda spent a great deal of time on my inner thighs, even spreading them aside for "access." Access was right, as she spent more time pressing against my dick than shaving me. They rolled me over and Lisa painted my fingernails while Brenda shaved the backs of my legs. This time I started spreadeagled for "access," and Brenda had no problem reaching everything this time. They turned me over again. Lisa leaned over me and said "Don't touch anything until they dry hun." She reached out and slid her fingers under m waistband, gently sliding my briefs off me. My dick was throbbing and pointing straight up. I blushed bright red.

"Don't be shy," said Lisa. I'm just as horny with all this. This is the hottest thing I've ever done."

"But I'm married, and she's right upstairs."

Brenda chimed in "Well even though we are here together, we both have husbands at home. And your wife didn't exactly stop you from coming with us, or follow to help or supervise. And frankly, I think you need a little "help" from a lover right now." And she reached over and stroked my twitching dick.

"Brenda!" Lisa said. "We don't have much time, and we still have to get him dressed." She slid her thong off.

"I know, but I never get anything this hard at home, and somehow I just want to play a little." Finished with all my fingers and toes, Brenda packed up her nail makeup and began to makeup my face. Meanwhile my dick was getting harder and bigger, straining for something to rub.

Lisa held her thong near my face. "See, you have an erection, but I am dripping about this, so don't feel you are alone." I inhaled deeply, taking in her scent. She notice and like it, and gently held them closer. I licked them and could taste that salty mix. A drop of precum formed on the tip. Lisa took her turn at a taste and licked it clean. I moaned, but she was a woman with a purpose and had already moved to put her wet thong on me. Once on, they debated the state of my crotch, and decided on more shaving. Off came the thong, out came the razor, and in no time as smooth as the day I was born, balls, groin, and ever throbbing cock. The thong looked hot on me. My body loved its silky smoothness, and the wetness just reminded me these women were as horny for me as I was for them. They shaved my chest and arms as well, until they were equally smooth. They added a well padded and stuffed bra, a little more silkiness in a slip, then a dress of Brenda's that draped well on my frame.

"Baby" she said. That looks so hot you have to keep it. It looke good on me, but never like that. Lisa teased out my hair and added a stylish straw hat. Last they added a pair of nylons...shoes weren't happening for my size 11's. Off we went down the hall towards the big show.

On the way, they tried to coach me on how to act, how to talk. But I told them there part was over, the show was going to be mine. They put the guys off stage for a grand enterance. The MC introduced the first team, and played with them about why there guy bolted. It loosened everybody up, and he gave them each a drink voucher for being so goodhearted about it all. Next up was the big guy. He did dress, but made a joke of the whole thing. He kept his sneakers and athletic socks on, and his striped boxers spilled out below the hem of a tiny mini skirt. His girls had painted a big heart around his tattoo in neon orange lipstick, his bra was unevenly stuffed, and he smoked a thick cigar with lipsticked lips and garishly painted eyes. He stepped out and comically did a model pose or two, then flexed his massive biceps, growled at the crowd and took his place beside his teammates. The next "girl" stepped out. Stunning in a silver lame gown that fit like a glove, made up tastefully, and wearing matching heels that actually fit his little feet, he sashayed out on the stage and batted his eyes at the audience. The crowd went wild, blowing kisses, whistling, and catcalls accompanied his little stroll. The MC asked him questions which he answered demurely. The MC admired his figure, the fit of the clothes and the shoes. He knew how to use those heels so well, I think he wasn't his first time.

My turn. I must've looked good, because my applause was just as loud on my entrance. I played it different though. No model stroll, instead I shuffled up to the guys in front, pinching heir cheeks, mussing their hair, and even dropping into the lap of a linebacker sized guy on the aisle, wrapping my arms around him and posing cheek to cheek for the ship's cameraman. The MC waved me up to him, and I turned it up again, wiggling my ass, both for what the crowd saw and for the feeling Lisa's soaked thong was giving my ass. My interview went well also as I was not about to be outdone.

"Well folks" the MC intoned into his mic. It looks pretty close her between teams 3 and 4. Let's break it down and vote with your applause. First of all, whose dress looked better?" The applause roared for us both about equally. "How about hair and makeup?" Same result. "How'd you like their walks, did they make an entrance like a starlet?" Apparently we both did this well, as they roared their approval of his elegant stroll and my little vamp act. "OK then we need a tiebreaker." I noticed team 4 is just wearing stockings while team 3 has beautifully outfitted their girl in heels, and he is walking with them like he's done it all his life. SO team 4, unless you have an ace up your sleeve, team 3 will take the prize.

So it was all on me. I knew I had it, but after all this, I wanted the max impact. I looked at the crowd. My wife was laughing so hard she was doubled over and red in the face. Her family was there too, and they were snapping pictures and joking like mad. Brenda and Lisa were shouting go for it, you've got this. I held my hand up to hush the crowd. It is amazing how feminine a man's arm can appear one shaved, and it gave me control. I tuned my profile to the audience and bean to slowly hike up the hem of the dress until the lace of the thigh highs showed. I looked at my competition. He too stepped forward, and slid his skirt up to reveal a sexy lace top. He took it further though, revealing sexy black lace panties, and turned his back to reveal a sexy bow on a high hip cut. I matched him, and the crowd noise let me know I'd won when they saw how much I'd shaved. But when I turned around, and they saw the rear of the thong in the rear of the model, the noise went to a whole new level.

As I left the hall, my wife told me she'd see me tonight at dinner. She was still laughing about it, which was a relief. What really surprised me was when she said "I hope you really enjoy getting cleaned up and back into your own clothes. Just save some for me when you come home. Oh, and bring the stocking and panties, I like them on you."

On the way to the girls room, Lisa and Brenda's hands were all over me. Once in the door, they pushed me right to the bed. Lisa lifted my dress and dropped to kiss my cock through the thong. Brenda pulled her shirt and bra off and buried my face in her chest so deeply I was afraid I might suffocate.. They both worked to remove the dress, the slip and the bra (which looked great under the dress but ridiculous without it). I lay there in the thong and stockings while Brenda began to kiss me. My hands explored her breasts. She dropped down on me and pulled my cock from the thong taking it deep in her mouth. Lisa was now out of her clothes and told me she had been dying to come all day, so sh wasn't waiting for Brenda to finish. She climbed up and mouned my face, moving around for maximum stimulation as my eager tongue tasted the source of the wet tease in my crotch. It didn't take long for any of us to cum, but none of us were ready to stop either, and we spent the whole day in a frenzied feast of skin.

Later that night I walked back to my room. Though the girls had cleaned me up and removed the makeup, I kept my word, and wore the wet thong and stockings as trophies beneath my own clothes. I could barely walk, and felt spent from a day of first extreme stimulation and then continual release. But somehow when I walked into the room and heard the words "That was the sexiest thing I've ever seen you do" my satin encased friend sprung to life.

"You know she said. I think we need to take you shopping for all new underwear."

I couldn't speak to answer. My tongue was already busy doing something else.

maninconn
maninconn
2,103 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
4 Comments
Kitist02Kitist02over 7 years ago
Skipped it

I skipped over this one for quite a while until I stumbled over it while looking for something else you wrote. Once I started reading it I had to finish it. I love your open-ended ending, one that leaves all kinds of room for sequels.

I been on cruises, and this particular madness is mild compared to some of the fun on a Hedonism cruise... Great job, and a very fun read.

OverthefallsOverthefallsover 10 years ago
Almost funny

But I think most men would have dumped the thong and stockings in the trash. And when the wife suggested new underwear? He would have made it quite clear that his "show" was a one time thing. In his place I would have been after the families pictures just to make sure his performance didn't live forever in family lore.

TavadelphinTavadelphinover 12 years ago
OK it worked well -

LOL it required the wife to be who she was to avoid making it all fall apart in the end but you pulled it off very well -

Nicely thought out and well executed thanks very much -

AnonymousAnonymousover 15 years ago
Very Sexy

I loved the fantasy... I hope you introduced your wife to your new friends and that they come prepared with a nice hard strapon for you!

Share this Story

story TAGS

Similar Stories

The Wolf Wears Fleece She underestimates him when she says she wants to swap.in Loving Wives
The Bridge Just another simple cuckold story?in Loving Wives
Words Can you destroy a betrayer with just words?in Loving Wives
Equation Sometimes love adds up.in Loving Wives
An Unexpected Reaction To an unacceptable situation.in Loving Wives
More Stories