Cockland Island Pt. 01

It’s actually called Huntington Island.

And it’s been around a long time and most of us in the area didn’t know much about it except they brought in guests and stuff by sea plane and set out for a lot of food and deliveries.

I mean it was a mystery and not around town. Most people worked there from town ended up staying there because it was this private resort then found high paying jobs elsewhere.

And it was an “Adult” resort so there were no minors ever hired, no rumors or bad stories other than it was a rich place.

I was in my second year of college when I found out everything and joined up.

I was fishing with friends on a drunken weekend and we’d been partying a little hard on my friend Mark’s boat. I was really drunk and we ended up smoking some pot and then I decided that I wanted to go to the lights we seen at night on Huntington Island.

Mark and the guys tried talking me out of it but it was such a good idea while I was that buzzed. So I peeled out of my clothes down to my underwear and dove off the side and swam to the lights.

I will give the guys this much credit they stayed until I made the dock and was waving to them.

Then I staggered around wandering until I found a party.

Lights, music, laughter, voices and lots of sex sounds and moaning.

I walked in literally on this orgy and it was all guys.

Well all guys and she males and like wannabe she males.

All kinda cute or might end up being cute all of them getting fucked by these guys. Big guys all pretty well muscled with really huge cocks. Some were sucking them, some were stroking them, taking turns, some getting double teamed.

I just stopped and stared until I got noticed by this big guy and he came over.

He was a really ripped, muscled hard working looking guy about six foot four and over two hundred pounds of muscle and a huge cock.

“You must be the new girl.”

“I’m the what?” He was looking at my cock which while average was like half the size of his, maybe less depending on how much girth he grew.

“The new girl.”

“Hey I’m not a girl.”

“Then you’re trespassing?”

“Uhm...sorry? Am I in trouble?”

“Yeah a lot.”

Now I was pretty drunk so part of my brain was doing it’s own thing and that got this nudge by this she male getting fucked in the ass crying out and spurting cum out all over the floor.

And my brain said I could do this.

“Looks like I’m the new girl.”

He looked at me and grinned. “What’s your name new girl?”

“Uhm... Nikki.”

“Well c’mon Nikki let’s get you a drink.”

I remember thinking that a drink was a good idea.

The guy led me to this bar inside and a drink turned into three and smoking a joint and eating an edible and taking a pill and getting blasted.

And watching a haze of sex and people, of guys but definitely not like the guys in charge fucking them.

Us.

I am completely hazy on when it happened but the guy who caught me had my boxers gone and his fingers in my ass as he lubed my asshole up.

That I noticed because it felt odd when I was staring at the others spaced out and then it felt good.

Really good, deep massaging my insides good and then before I knew it I went hard as a rock despite being that drunk and came from getting fingered.

It took no effort on his part to push me over the end of the sofa and bend me over and sink this huge cock into my ass.

It hurt, it hurt and didn’t the stretch felt impossible.

The kink felt through the roof and so did the heat of his huge cock.

It got better, slicker, more stretched out.

Filled me, utterly filled me with thick hard cock and as drunk and high as I was it was totally clear what was happening to me.

Faster, and faster until that cock dominated me and my drunk body as I came again and again crying out “Joe!”

I’ve no idea if that was his name but it was a good idea at the time.

And I was so just fucked, just literally fucked up that when some big cock ended up in my face I took it in hand and clumsily stroked and sucked it.

I’m sure there was more but that’s all I remember.

Waking up was more me being still higher than hungover and my body hurt. It was just us girls there and one of them passed me a can of pop and that helped.

“The boss wants to see you.”

“The boss?”

“C’mon new girl.”

She gave me a robe and she led me to an office. The place was an actual resort and had cabins and other stuff here and it was all hot big rough guys and she males.

Inside the office looked high end and the woman there a stone cold fox.

She was watching the security tapes with me definitely trespassing.

“You trespassed here that’s pretty serious.”

“Uhm I think I paid for it, though.”

“Oh yes, I heard about Nikki arriving. Still....”

“Still?”

“We could be sued or you could.”

“I’m broke.”

“Well Nikki, Sweetie you’re broken in.”

I couldn’t help but blush and stare as more of me was on the screen with “Joe” and getting fucked and him making me cry out and cum as he fucked me with that giant cock.

And not just him.

There was another guy, and another guy taking his place, mounting me from behind and I could remember the feeling of it all.

And as that was happening I started sucking cock on screen and from just sucking to having my head gripped and my throat filled.

I was shivering watching it all transfixed.

Until she came over rewinding it with a drink and after a sip she kissed me and looked at me in my eyes.

“You’re the new girl Nikki.”

“I’m the new girl Nikki.”

“You have to make arrangements to work here full time, the place is on site and the contract is for a year long.”

“I’m in college.”

“The money’s worth it.”

“Money, how much?”

“Forty to start.”

That much for here and getting fucked?

“What do I have to do?”

“Just be the new girl, you go through training and then entertain the men and there’s a chore board to get all the little things done around here.”

“Okay...Okay I’m in.”

My video was playing again and my aching insides were aching in a different way wanting to be filled again like “Joe” was filling me on screen and making my cock spurt cum without getting touched.

My new “Boss” fingered me as we watched and touched something inside of me making me cry out and spurt cum over the floor.

“Abby take Nikki to the spa and get her started while I get legal stuff set up.”

I was still dazed when Abby led me from there to a large cabin full of she males all getting groomed and primped and prettied up.

“This is Nikki she’s new and she needs made over.”

The place was a spa or salon and all full of guys being definitely not guys.

Hair being done, make-up, lashes, nails, brows and bodies that went from dressed to naked tits out from large awesome breasts to tiny ones or none to dicks out and those went from average to tiny to most being caged?

I was staring at that when I was taken by Abby and three other girls to a shower.

It started with a joint being passed around as they undressed and they were all caged she males with cute sexy underwear and very boyish but femmy features.

We smoked and I asked. “What the fuck are those.”

Abby said. “Sissy cages, it makes out cocks into small little clitties and proves we don’t need our manhood to cum at all.”

Another girl says. “Not even cumming we don’t need our manhood at all I don’t need that bullshit.”

They’re all nodding. “You’re getting me into one of those things?”

Abby shakes her head. “You’ll do it, we all pick out our own, you’ll see after training.”

I didn’t know what to say after that so I let them take me into the shower.

It went fast, the cream stuff to get rid of my body hair, the heavy duty scrub down and then shaving my head all leading up to getting hosed out and shown how to do that and keep clean inside.

Then it was drinking these girly drinks and having another joint as they got me high and we had ice cream shakes with the body building powder in them for breakfast.

Abby took me to a cabin and it was set up with stuff and it was a shared room with two beds and there was this guy, she-male bent over the bed all propped up and watching a video on a laptop big earphones on and this workbench like piston dildo machine fucking their ass non-stop.

I watched her shiver and moan through cumming with just getting fucked by the machine.

She moaned as she did all girly and said. “Fuck, fuck the man out of me, I’m a sweet girl, I’m a sissy girl, my sissy pussy feels so good.”

There was a second machine at the other bed for me.

“I’m not sure I’m ready.”

Abby kissed me and then the others did.

It was all touches and smoothness and someone started sucking my dick and someone else started lubing me up inside and then once we were on the bed a viberator slid inside of me.

I gasped, cried out when they found my spot and that definitely made me cum instantly while there was a mouth around my cock.

Abby and her friends kept the sexy stuff up and the vibe fucking me going until I was blissed out enough that they rolled me over and got me into position and the dildo piston machine ready and I groaned with pleasure, relief as it filled me because after the vibe I was really enjoying something in my ass.

I was still gasping and moaning as it worked hard and fast and non stop feeding that dildo inside of me over and over and pretty hard and fast.

It fucked me hard until the girls put down this laptop in front of me as I was tripping and earphones over my ears and I watched videos of sissy hypnos telling me how much I want cock, love cock, love being a sissy, having the masculinity fucked out of me, feeling the guy slipping away or fading or going away with every thrust, loving cock, sucking cock, facials.

Thrusting, pounding, pistoning through me...gliding through me until it became pleasure inducing this rhythm in feeling, breathing, cumming.

Cumming even when the tank was literally dry and still the feelings came pouring through me.

Matching the words on the screen and in the headphones.

It was all this non-stop bombardment all while high and completely enforced by getting my pleasure rushing through my brain in this whole new experience.

Hours of getting fucked like that changes you.

It changed me.

I was coming down when they came back and took Jill and I off the machines and then to get cleaned up and dressed.

I couldn’t walk right.

Which made me smile.

I felt more than just stoned but overloaded with happy.

Dressed was panties from stores that we got to pick out and a nice simple dress them fake nails and our toenails done to match and then wigs and make-up.

Then we picked out our cocklette cages and our own butt plugs.

Always keep clean inside as possible always be filled with a plug to be ready, to know what you are and to make you sway.

And Abby was right I was more than happy to cage it like the rest of them and to feel that pressure and everything that’ll work and shrink my dick.

I feel it working as we walk and the butt plug is inside of me helping me sway as they’re teaching Jill and I how to walk and hold ourselves.

Just like the videos and the audio hypnos and just like them here.

Then it was off to supper and the common areas.

I went blonde and Jill was a redhead and it took us a bit of a tour to get shown the dining hall and common games room and other free spaces then we were shown the cards room, pool tables, all really high end stuff and places some restricted by having no access to staff unless you’re a chosen date.

The entire time walking around was getting looks from these big buff big cocked men here, these definite alpha men into us sissies to pay for us.

And I found myself looking back.

Would his cock feel good? How would he fuck me?

What would he taste like?

I can’t really remember feeling indecisive about it either.

I wanted it.

Wanted this.

And once Jill and I were getting introduced around the dining hall and getting some food we were left on our own.

Well until the “Men” came around who were into the new girls.