The Captains Hook Transgender & Crossdressers


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Disclaimer: for the literary perfectionist, I apologize for grammar, spelling, I do use spellcheck and grammar check, but sometimes it doesn’t work right.

This is a long and I promise it will get you there! halfway through, and all the way to the end if you want to read that far.

The Captains Hook

Being an intern sucks! I thought after graduation I would land the perfect job, but life really sucks.

For six months, I’ve been an intern at one of the coolest P R companies in the industry.

For six months life has been hell. I moved out of mom and dad’s house, and share a house with six other interns.

The company pays the rent and utilities, and mom and dad pay for my food. It sounds like it should be the perfect situation for anyone.

But, the ridiculous demands of the company, basically has us as 24 hour oncall slaves.

In return, they announce two fulltime positions every year right before Thanksgiving. I need one of those jobs so when I go home for Thanksgiving dinner with the family, I can finally sit at the table and not be harassed by my brothers and sisters.

The house is either always busy or always empty. The six of us fight for dominance over the living room, one of the two bathrooms, the microwave and the washer and dryer.

Typically, the alpha male Chad, and the alpha female Stacey win out every time. That leaves me, Irene, Julia and Tiffany waiting for our turns.

Irene is of Korean descent, she stays quiet doesn’t say anything she is very passive.

Julia, she’s one of those dark Gothic types that keep to themselves, the loaner type mad at the world about everything.

That leaves, Tiffany and myself. We usually buddy up, she’s just like one of my sisters and everyone at the firm calls us the twins.

I think it’s because we are both blondes, both skinny, and both of us have shoulder length straight hair.

Tiffany is always watching out for me. She’ll come in and take my laundry and do it with hers. And in return, I make us dinner.

Since we’re always trying to catch up on work, she usually comes into my room. Chad is always watching TV, he never has extra work for some reason.

Tiffany always climbs up on the bed and sits with me, her and I both work for the same boss, Mr. Jackson. Or should I say Mr. dickhead! He’s a total dick, Mr. macho always yelling at us and we do all the work for him.

We always get teased at work, not only because we look like twins, but, because we’re always sidebyside, always joking around when we’re with each other.

I can’t help it. Tiffany is cute, a bit nerdy, she is perfect. Stupid Chad has tried to hit on her many times. But thank God, she always turns him down.

Stacey always tries to recruit Tiffany to go with her on some of her events. Stacey is this big tall, brunette slut. It’s rumored that she will suck and fuck anything that moves to try to get ahead. Her and Chad are definitely popular around the office floors. I think it has a lot to do with their fraternity and sorority bonds.

I always use Stacey’s image to jack off to. Thinking of her, on her knees or bent over someone’s desk taking it deep. But lately, images of Tiffany flash through my mind.

The other morning when I was getting dressed and I was getting my underwear out, folded in with them was a pair of powder blue nylon panties. They were cute! Holy shit, a pair of Tiffany’s panties must’ve static cling themselves to my underwear and got folded up by mistake.

I told them apart. I held them up, looking at them. So so pretty. The sheen of the nylon, the cute little satin bows in the front, sides, and leg openings. The stitching gathering the elastic makes them cute! My cock jumped, thinking of them touching, hugging Tiffany’s ass and pussy.

Wait! I’m thinking about Tiffany’s ass and pussy? I can’t. She is my best friend, I think of her as one of my sisters. I never really thought of her in that way before.

But my raging hard on was thinking differently. I brought them up to my nose and smelled tickling my face my lips.

I quickly wrapped them around my cock! I almost came right there soon as they touched my skin of my shaft.

I had to jack off, and quick. But Chad was in the kitchen so I could not do it here in the room. I did not want to get caught carrying them into the bathroom, so I decided to step into them, and wear them under my plaid pajama pants and go to the bathroom.

I was nervous, shaking, and excited all at the same time.

The feeling of my foot and leg sliding through the elastic openings as I slid them up, had my cock throbbing and bouncing.

When I got them all the way up, they were tight, but felt wonderful as they encased my hard on with electric pressure.

I didn’t think I was gonna be able to walk without coming. I pull on the pajama pants and threw on a baggy sweatshirt. Made my way to the bathroom.

Quickly I locked the door, pulled my pants down and kicked them off. The feeling of the sweatshirt sliding up my panty covered ass was amazing.

I turned and looked at my ass in the mirror, looking over my shoulder, rubbing the front of the panties and my hard on.

The image in the mirror was Tiffany. I guess from behind we did look like twins. I had my hand inside the front of the panties wrapped around my cock.

It only took a few strokes to make me cum. The sensation and electricity shooting through the tip of my penis head as it rubbed the nylon was enough to make me pass out. My legs were shaking.

My cock strained to spurt the come through the material. I lifted up the sweatshirt to witness a beautiful sight. Globs of white gooey pearlescent cum flowing through the powder blue fabric.

There was a knock on the door. I panicked. Yelling, just a minute. It was Irene, she wanted to get in to use the bathroom.

I grabbed toilet paper and wiped the come off the side of the panties. Stuffed a big wad of toilet paper around the head of my cock. And jumped back into my pants.

When I open the door, Irene was looking at me weird. My face was flushed red. And what I didn’t know is you could smell the cum in the air. Irene walked past me, whispering, disgusting.

I headed back to my room. I kicked off my pajama pants and right at that time Chad walked in.

I sat down on the bed really quick. I hope he didn’t see what I was wearing. I grabbed pants, threw my legs into them and slid them up and jumped in as quickly as I could when Chad’s back was turned.

Julia and Stacey were yelling at us that we were gonna be late. I grabbed my blue long sleeve button down shirt and tucking it down into my tan khaki pants. My hand brushing my cock and the nylon panties as I tucked my shirt in.

How was I going to get through the day wearing Tiffany’s panties under my clothes. I was scared.

I was scared, almost being caught wearing panties and jacking off by Irene and Chad. How could I get through How could I get through the whole day at work knowing what I’m wearing. I was scared thinking someone is going to find out someone will see, someone will know.

Maybe I will be able to change into my underwear at work. I stuffed a pair in my backpack and thought maybe I can do it on break or on lunch in the bathroom.

When I got into the van with everyone, Tiffany was waiting for me to sit next to her. She could see the look on my face and knew something was wrong.

Irene was shaking her head as I slid by her. Chad hopped in, shut the door and took off in a hurry.

We went sliding around the corner, and I slid hard smashing Tiffany up against the window of the van. Feeling of the nylon panties under my khaki pants had me squirming.

And when I smashed up into Tiffany, electricity shot through me as I felt her touch in a different way. my cock was super hard instantly.

Tiffany was saying, down boy! Easy there killer. You at least have to buy me a drink before you jump my bones.

I was embarrassed. I slid myself off of her giving us distance in the seat. When I looked at her, her smile was different. She was grinning. She asked me why I look so flushed and bothered.

I stammered and stuttered trying to come up with an excuse. Didn’t get a chance to get the words out as we came to a screeching stop my head hitting the seat in front of me. We were at work.

When we were getting out of the van. I was bent over getting ready to step out, and Tiffany had her hand on my ass, pushing me out the sliding van door.

I think I came a little. Her hand on my panty covered ass under my khakis had me all flustered.

As we walked, I was silent. I wondered if she could feel I was wearing her panties then I thought as I was bent over, could she see the panty lines through my khakis. I didn’t wanna look at her but when I did, she was looking at me. She still had the same grin on her face when I got into the van.

I tried to keep my distance from her at work, I couldn’t be next to her and take her touch anymore, especially while wearing her panties. Thank God I still had the toilet paper wrapped around the head of my cock soaking up whatever cum that was leaking out.

I finally had time to take a break. I grab my backpack and headed for the restroom. it was empty and I got into the end stall.

I kicked off my loafers, dropped my pants, sat on the toilet. I pulled the toilet paper out of the panties and dropped it in the toilet.

I wanted to jack off again one more time before I took the panties off. My cock was semi hard and never went soft the whole time I was wearing the panties.

Since the restroom was empty. And this might be my only and last time with these panties, I decided to sit there and rub one out.

It didn’t take long I was pumping fast and pump umping cum fast into the nylon fabric. I stepped out of my pants and slid the panties down.

I started to kick my feet out of the leg openings of the panties and accidentally kicked them slightly into the next stall.

I was reaching down to grab them when a hand reached down at the same time touching mine, grabbing the panties.

The hand picked the panties up and they disappeared. More mortified I quickly grab my underwear out of my backpack, stepped into them, put my pants on and shoes and hurried out of the stall.

I was washing my hands in a panic. Looking in the mirror, looking at the stall that was next to mine, hoping nobody would come out.

Who was in there? I could hear noise. It was a similar noise to the sound I was making when I was jacking off. Someone was jacking off in the stall. And they had tiffany’s powder blue nylon panties filled with my cum.

I wanted to stay and see who was there, to see who it was, but being scared I quickly ran out and back to my cubicle.

I kept looking around to see who was missing, who could have been in the stall, who could it be who was in there jacking off using panties the same way I was.

Down the hall came Chad, Stacey and Mr. Jackson. They had a funny grin on their face and were talking to each other as they were walking.

I thought, was it Chad? Or Mr. Jackson? It couldn’t have been Stacey. She would not have been in the men’s restroom that had been one of those two.

Now, I was scared 10 times over. Scared that my roommate knows what I did. And scared that it was my boss who knows what I did and is going to fire me. But which one was it?

In the break room, I wanted to hide. Tiffany came up and sat aside. Me asked me what was wrong. She could tell I was scared and nervous.

I didn’t know what to tell her, how could I tell her what it just happened today. She broke the silence by asking me if I got her present that she had left in my underwear.

I looked at her funny. I must’ve been as white as a ghost. She said it’s OK don’t be embarrassed.

She said, those are my favorite pair of panties. And they match the bra that I’m wearing today. She reached in the top of her shirt and pull out a blue bra strap.

She said, I think they must’ve been stuck to a pair of your underwear. That’s why you’re all flustered, he found them today and we’re embarrassed to tell me.

She then shocked me, when she said, I definitely knew that you had found them when we were getting out of the van, I could feel them when I was pushing your butt to push you out of the door.

How do they feel? I know when I wear them they feel amazing. All I could say was, good.

Tiffany said, you know, you’re welcome to wear any of them anytime you want.

I started to stutter and stammer trying to find words to say.

She said, it’s OK, it’s OK if you are gay and want to experiment. And I can help you.

I looked at her, and said, what! I’m not gay! What makes you think that?

She said, all these months together, Chad is the only one who’s been trying to get into my panties, well actually trying to get me out of my panties.

Today when I was pushing you out of the van, I could feel my panties under your pants. I had a feeling that they had gotten in with your clothes when I did the wash. But, I wasn’t expecting you to wear them.

I told her, I’m not gay, the only reason I put them on was I was thinking of you, I always think of Stacey when I jack off, I never thought of you and that way. That’s why I’ve never tried anything with you.

You are my best friend, I never really thought of you in that way until I saw the panties today. When I pick them up, I don’t know what came over me.

She said, if you’re not gay, then why are you wearing them?

I told her, that they made me instantly hard when I saw them and I had the jack off. There was no way I could go to work with a raging hard on.

So, the only way to sneak them into the bathroom was to wear them under my pajamas. All I was gonna do was wrap them around my penis and jack off with them.

She looked at me, grinning, and said, what is it with guys and girls panties? My old boyfriend used to jack off with my panties he would keep them after we had as trophies.

I stammered, saying I never, this is the first, I never tried it before.

She asked, well? Was it worth it? Did you like them? What were you thinking about when you were jacking off with them?

Flashback of the image in the mirror rushed through my mind, her ass in those panties with the baggy sweatshirt on, her blonde hair coming down the back.

I was thinking of you. I was thinking of how they were hugging your cute little ass. I was wondering how they must’ve felt if my hands were sliding over them, rubbing you.

She elbowed me, saying, you, naughty boy. When we get home, I do want my panties back. And if you buy me a drink, maybe I’ll let you touch me in them.

I didn’t tell her that I wasn’t still wearing them. Now I had to figure out who had them. Or maybe I could just buy a new pair? What brand were they? I didn’t look at the tag how would I be able to find them?

Back at the house, I was in the room surfing the Internet, looking for those panties online. Didn’t hear Chad walking in the room. He was standing there watching me look at panties on the computer.

Suddenly, something landed on my shoulder, I turned and saw Chad and grabbed Tiffany’s panties that he had placed there.

Chad said, I think you dropped these. if you’re gonna buy more, can I suggest a pair of pink ones. I think you would look good in pink, especially with your blonde hair. You will look just like your twin.

Don’t worry, your secret is safe with me. At the frat house we had a panty boy who used to clean our rooms. And my cock.

So maybe you need to start cleaning our room with just your panties on.

I told him they were not mine. He didn’t believe me. I did not want to tell him whose they really were, because I wanted them back, Tiffany wanted them back and I wanted to touch Tiffany in them.

With the panties in hand, I went to the kitchen and grabbed a couple of white claws, and made my way to Tiffany’s room.

I knocked on the door, one side of the room was a mess that was Stacey’s bed. Now I know why she always wanted to be in my room. Stacey was a complete slob.

Tiffany was sitting on her bed with her legs crossed and her laptop in between them.

I sat on the bed next to her and opened the white claws and laid her panties on her laptop.

She slid back on the bed, pushing the laptop to the side with the panties lying on the keyboard. I sat beside her and we guzzle down the drinks while we were talking.

We were tipsy, lightweights. Our conversation turned to men jacking off with panties. She told me she never watched her boyfriend do it, but knew that he always did because of the smell and stain he left in the panties.

She picked up the panties, held them to her nose and smelled, saying, see, they smell like cum. I was laughing. She brought them up to my nose to make me smell them. She then stuffed them into my mouth.

I was dazed, confused, and buzzed at the same time. The shock of her stuffing her panties in my mouth had my head spinning, but the taste of the nylon with the strong, pungent smell of cum filled my mouth and nostrils.

Tiffany was laughing, saying, oh, you like the smell, don’t you? It seems like you are enjoying the taste as well.

I pulled them out of my mouth and stuffed them in hers as she was laughing.

She pulled them out and started kissing me. The flavor of her kiss was amazing, the alcohol infused with a slight hint of semen.

We were kissing and fondling each other. Tiff had reached down and fished my hard cock out of my pants while I was kissing her neck.

Tiffany wrapped the moist panties around my shaft and started stroking.

I started kissing my way down her neck to her collarbone working my way into her cleavage.

I worked her buttons loose and was gripping and licking her breasts.

When I locked onto one of her nipples, she exploded with fire. Her hand was pumping me furiously. I was about to cum.

She must’ve sensed it. She pushed me up off of her tits, and said, I wanna watch you cum. She moved her head down to my lap without missing a stroke. She stuck the tip of her tongue out tickling the tip of my cock.

She stopped for a second to encase my meat in the blue fabric, and resumed her motions. She started to lick the top of my cock like a lollipop. Licking the blue panties. And she was soon rewarded with her treat.

She tasted the first glob of cum squirt through the fabric. She stopped licking so she could watch me cum. She pumped my shaft harder to get out as much cum as she could squeeze out of it.

I watched her eyes light up as the cum strained to ooze through the powder blue nylon panties. globbing up sitting on top of my cock soaking the fabric.

She stopped pumping me when she realized she had milked my meat dry. She started to lick the cum off of the fabric. I had to stop her as I was too sensitive and jumped and flinched with every touch of her tongue.

Tiffany came back up and kissed me. Her tongue wet and coated with cum. She was fiendishly feeding me her tongue and my cum.

Just then, Stacey walked in.

Stacey yelled, what the hell is going on here?

Tiffany broke our kiss, I tried to sit up, but forgot Tiffany still had her hand and panties wrapped around my softening shaft.

Stacey said, nice! a little handy work going on I see. hey, are those the blue panties Chad was telling me and Mr. Jackson about?

So, whose are they? Do they really belong to you Tiffany? or do they belong to you? Travis? and how did they end up on the floor of the mens restroom anyways?

I was fumbling trying to cover myself up. Stacey, being the dominant alpha female, came over to us, snatched the panties off of my cock, right out of Tiffany’s hand. She held them up. She looked at them and said, oh how cute! They’re far too cute to be yours Tiffany. So they must belong to Travis.

Stacey held him up to her nose, moist and wet with cum, she inhaled. Then she said, Yep they are yours Travis. I smell cum on them. You naughty little boy. Do you love to cum in your little panties. Were you so excited you had to rub your little clitty in the restroom?

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