[Fiction] Sissy life On Deck

[Sissywannabe]

Hey guys I'm starting a new story based on some of my personal fantasies, please pm me with any and all ideas as well as dares. Please comment all advice as this is my first story. Please excuse all grammar mistakes and please be pacient as I will only be able to write in my free time while on my phone.



It was my first day on the SS Fem, it was my first time ever on a cruise ship, but I won a free semester so I decided to take it. I felt as if it would be a fresh start as I wasn't the most popular or cool kid in school and a month on a cruise ship was sure to change it.
My name is Logan, I'm a sophomore and am only 5 foot three, the shortest in my whole grade. I run cross country and an extremely skinny because of it, great for being on a cruise.
As I was packing for my semester on the water and getting ready for all of the girls in their bikinis I started fantasizing about my adventures abroad, all of the different countries were sure to be awesome, but even better was the boat, it was huge with hundreds of rooms and four decks!!! As I walked up to it the first time I couldn't believe how big it was. I took a deep breath and walked aboard, I couldn't believe it, everywhere I looked there was something new, finally I reached the top deck which was reserved for the students and their activities, it had its own rooms, pool and classroom. I headed to the classroom to meet everyone, but when I walked in I could not believe my luck, the teacher was drop dead gorgeous but didn't even compare to get students, all of which were beautiful women, many blonde with dark tan skin.
But when I walked in every girl ran to me, it was I first time for me, I felt super hot, but then found out I won a free semester on an all girls school. I knew this would be the start of a great semester!!!

[Crossdresser5]

I like it so far can't wait for more

[Dirty_Slut]

love it! keep it up

[Sissywannabe]

Over 500 views!!! Thanks guys!!!

Chapter 2
My first order of business was to meet all of my new classmates, Lexi was a tall Burnette with a beautiful face but lacked the assets that would make her hot. She immediately came up to me asking all of these questions but giving me no time to answer. Next was Heather, she was the least attractive of them all and gave me nasty remarks about how my hair was cut in a buzz rather than being long. There were a few other girls that introduced themselves, but none stood out as much as Ashley. She had a beautiful face with amazing blonde hair and ocean like blue eyes, her long legs that led to an amazing ass were just enough to start a tent in my pants. She was super nice and funny, I hoped we would get to know each other a lot better.
But in the middle of our conversation the teacher came over and broke us up. Ashley was sent to her seat while Ms. French sent me to the bunk house to find my dorm.
As I walked across the boat to seek out my dorm I noticed the extra large space that was between each room showing that I would have a nice big dorm, but in the very back was one bathroom/ shower room, this was sure to be a hit! As I walked the length of the corridor I found a door with a small ribbon on it and a sticky note, I picked up the note and read it aloud, " Congrats Logan! You have been selected to win a one semester free trip. We hope that you find your stay very enjoyable."
I pulled on the handle to find the door unlocked so I entered to put all of my stuff up. I enter the room to find the best suprise ever, I would be bunking with Ashley!!! Her pictures were all spread out across her desk which sat next to mine, her bed was on the left side of the room and mine on the right. I go to sit my bag on my bed but find a short navy blue and plaid skirt and a white polo. The letter that laid on top said that this was my jersey and I would be required to wear it while in class on Mondays and Wednesdays, I would be given another white skirt and a pink polo to wear on Tuesdays and Thursdays. Out of class I could wear whatever I wanted. This was not good, I couldn't wear a skirt I am a boy. Just then Ashley entered the room wearing the white skirt and pink polo, she said "Oh my god this is going to be so great that were roommates. Oh my god are you going to wear that?"
I tried to say no but the surprise that I just faced left me with fear so I said "yes" out of nowhere, and immediately she pulled my shorts down and slid up the skirt.
To be continued

[Crossdresser5]

Why can't this be me

[dareme1330]

It was a very good start

[mrpropel]

Liking this story, keep it up!

[Sissywannabe]

Chapter three is finally here! Remember to pm me any ideas for my story or dares for being a sissy

I immediately regretted my reaction to her silly question, I'm not a girl I'm a boy, but as my dick grew even harder, showing clearly through the skirt that Ashley was putting in place. My erection was inches from her mouth, this realization caused my dick to grow fully erect.
"Oh my god" said Ashley, "your enjoying this aren't you, you little cross dresser."
"No no no no" I quickly disagreed, lying through my teeth.
" I know your lying, everyone is going to love this, tonight ill give you a totally new look, ill call Brenda over to help!"



"Hey Brenda are you ready to see the cutest thing ever?"
This was my que to walk out of the closet while wearing my new uniform, the navy blue plaid skirt with nothing on top and only underwear below the skirt.
"Holy crap Ashley how did you get him to wear that?"
"All it took was me asking him if he would wear it, it is his uniform after all, he's required to wear it."
This quickly made me realize I would have to wear a skirt everyday to class.
Brenda then said quite enthusiastically"Lets give him a full makeover and make him into a full on sissy!"
The next thing I know my underwear is on the floor as well as my skirt, I was completely naked as Brenda shoved me onto the bed and tied me spread eagle to the posts of the bed. I look up to see if Ashley was going to help me but she had a bottle of shaving wax and strips of what looked like paper, they were going to wax me!
" don't worry Logan this will be super quick and you'll legs will look much better in that skirt of yours." Said Brenda, Ashley then poured the wax all over my legs up until my pubic region, which I was glad for, I didn't want to lose my only bit of masculinity left.
In one quick motion, Brenda lifted a piece of the paper off the wax, tearing away my leg hair. This caused me to scream, the pain was horrific, but was rejolted after having the rest of my left leg completely waxed, then came the right leg. After this they shaved my arms, chest, eyebrows and neck, I was completely hairless except for the hair on the back if my legs, arms, head and the nether regions. But then a special bottle of shaving cream was brought out accompanied by a pink razor, they bottle was spread across my pubes and the razor made its way across ever so gently leaving me no pubes after a few passes.
I was then turned over and the waxing continued on my back until I was hairless from the eyebrows down. I was told to get dressed after being untied. My clothes were now on my bed, as I walked over to them I noticed an extra navy blue article if clothing, but it was silk, and they were panties. I tried to argue but was shown a lock that was already on my suitcase, so it was commando or panties, I chose panties. I slid them up my legs and my boner inner irately roared back to life, the softness felt so good and comforting I couldn't help it. Next was the skirt which I pulled up quickly to hide my boner, but it was still half visible due to the shortness of the skirt.
"Next is the bra" said Brenda and Askley in unison.

To be continued
What do you guys think so far?

[Dirty_Slut]

i love it! Logan is one lucky sissy

[Crossdresser5]

This is my new fav story
This is every sissy dream

[18_sub_TS]

Will there be any male interaction for the sissy. As a sissy always needs cock. But great story so far

[Sissywannabe]

Wow guys this is awesome so far can't wait to see how many views we can get, remember to pm me any ideas

I was already in a skirt and panties, next came the bra. I turned to face Brenda and Ashley and to my suprise, Brenda was halfway done with taking her bra off, the c cups finally released, showing a pair of quarter sized pink perky nipples, they were the first ones I had ever seen in person, but were quickly covered up by her shirt.
She handed me the bra and I immediately slid it on, struggling to get it on in the back. There was one problem though, I was perfectly flat while Brenda had fairly large breasts, so she took two gello looking blobs inside the two cups, ripping off a piece of paper before doing so, and she stuck them onto my chest and held them in place while counting to thirty.
"These here are called breast forms, they will fill in your c cup bras perfectly, I happened to find this in the acting department where they store costumes and props. They will stick for one whole week before falling off, but don't worry I have plenty more" said Ashley
"We'll have to take you by one day, I'm sure youll be wearing plenty of the costumes" added Brenda.
This was not good I thought, but I couldn't help but be arroused by the thought of being a sissy.
"I have an idea Brenda, why don't we take him by right now and let him try on some of the dresses in their?"
"That's a great idea Ashley, lets go!"
They both stormed out of the room taking me by the hands past the pool and the study center into a big storage room, inside it was dark and smelt of excess perfume, but when the lights came on, over a hundred different costumes came to life on either side of me, one labeled male, and one female, that's where they led me.

What costumes do you think he should try on next? Pm me with your answer and any other ideas or questions, next chapter should be up soon depending on the responses.

[Crossdresser5]

I can't wait to see what else happens
I check the stories ever hour to see if there is a new part

[Sissywannabe]

Finally have some free time so I'm going to try and make two posts today, please pm me if you would be interested in helping me write this story I just don't have enough time to post everyday and feel that if another author were to join me it would be much more enjoyable to the readers, pm me for more info.

Now back to the story

As the lights were turned on tons of colorful and girls costumes filled my eyesight, their were probably over five hundred girls costumes in the huge area on two different floors. The girls sat me down at a vanity giving me two directions, don't leave and don't stop masturbating and don't cum. Before leaving Ashley slid off her pink panties and handed them to me.
As the two girls walked away, I immediately brought the pink panties up to my nose taking a deep breath in of the sweet smell. I heard a click and looked up to see Brenda taking a photo of me with the panties to my nose. I immediately regretted taking that whiff so I tucked my head and slid the soft panties up and down my shaft for about ten minutes before the girls came back with three outfits each.
Brenda went first showing me a bright yellow dress that represented belle in the beauty and the beast, then a Cinderella dress and finally a wizard of oz outfit of Dorothy.
Ashley then took out a French maids outfit, a cheerleading outfit and a ballerina outfit.
They then took out a dice and said whichever number it lands on is the one you have to wear first.
I rolled the dice across the vanity and it turned out a one, which was very unlucky for me, Ashley went off to find matching heels and Brenda to get panties, a bra and makeup, I had to keep masturbating with the panties.
A few minutes later Ashley came back with six inch stilettos and Ashley with loads of makeup and yellow panties with a bra, the bra went on and filled my c cup breast forms perfectly and then the panties were slid on, the yellow dress was next it landed right below the panties. For about thirty minutes pictures were taken with me and of me to be used as black mail, I was then let out of the costume and forced to roll the die again, this time a six. So I slipped on the pink bra and tons of makeup, next came the six inch pink stilettos and the pink tutu and leotard that only covered my top. The tutu was held up by my rock hard boner.
Then Ashley taught me a dance and said I would have to do it on the stage in thirty minutes perfectly until I got it right, so I practiced and practiced, my dock bouncing everywhere, at the end of the thirty minutes I was led onto the stage and applauded by everyone of my classmates, it took me seven trues before I got it right, but when I finished I was applauded by boos and instead of receing flowers I got panties, 21 in total, I was totally humiliated, but then the teacher walked in and walked straight to me giving me a detention slip, to her room.

[Sissywannabe]

1500 views guys thanks

As I walked down the hall, dressed back in my normal clothes, sweatpants, tshirt and sneakers, except I was wearing the pink panties from earlier, I have to wear them at all times unless told so. This hall was very different from the student dorm hall, it consisted of an entrance to the classroom, multiple hall closets and one room that took up the whole other side, I knock on the door to hear Mrs French walk up and peer through the eyehole before unlocking the door, the room was very bright and opening but she brought me through the house dragging me throughout without saying a single word. We finally reached the end of the long hallway with multiple doors on each side where she told me to kneel and wait.
"Woah woah woah hold up, why do I have to kneel?"
"Because I said, and if you don't do everything as I say then you will be kicked off this boat."
I immediately kneeled, becoming submissive to every word she says.
She opens up the door next to the one I kneeled at, revealing two sections, one with lingerie and the other with nothing but a big cardboard box marked Mistress French.
She took out the box and closed the door before having me open my door and crawl in.
I crawled into the room, empty of light until she flicked on the lights after dropping the box onto a wooden table.
"I came to this school not only to teach and make lots of money but to find a plaything, I was hoping to have a female but none were submissive quite like you. So you'll have to do as my sissy bitch."
And all I could say was yes mistress.
Don't worry Noone will find out because I won't say anything and you definitely won't say anything. You will only have to come here when you get in trouble though."
This was good news I thought to myself. I was then told to stand up and go spread eagle, both my wrists were tied to opposite corners of the metal square, my ankles were then tied to the bottom at opposite sides.
My back was to mistress but I heard her digging through the box, I then see her appear in front of me with a pair of scissors, she starts on my shirt before cutting off my sweat pangs and throwing both in the corner.
"Just look at my sissy in his little pink panties" she said grabbing my dick through them and started sliding her hand up and down, it wasn't long before I came, then she disappeared to her box again, she came back and knelt down pulling my panties lower and attaching something metal to my now soft dick. Once I was allowed to look down I did, seeing a pink chasity cage with a bow tied to the top, and the key laying inside a jar of similar keys, but only one could unlock my dick from its prison.
Kapow
A leather paddle made contact with my exposed ass leaving a stinging feeling and me screaming. Mistress walks back to her box and comes back wrapping a leather strap around my head and tightening it up, it was a ball gag and my screams were now nothing but a light humming sound.
Something was rubbed on my ass and then something else shoved into it, I now had a buttolug in too.
This was going to be a rough detention.