Cockland Island Stories

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Cockland Island Pt. 03

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I think my dreams that night were pleasant. I was kind of still just transforming back then. But when I woke up, I remember the feeling of my butt plug in my ass was pleasing and that my caged cock was perfectly sissy cute and I was good with that. It was kinda a trip to look in the mirror and see it all. And walking with the plug, sitting with the plug....

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Cockland Island Pt. 02

by Sissyhalo1 on Dec 3, 2019
Transgender & Crossdressers

I knew I was messed up in the head and didn't care. I knew I was getting brainwashed but didn't care the videos, the drugs, the sex. These nice, big, muscular, handsome guys were there eating with us as we shared a table and were being really nice to Jill and I. In my normal life people are just sorta nice, not nice in this way. It was kind of cool and y...

Cockland Island Pt. 01

by Sissyhalo1 on Oct 8, 2019
Transgender & Crossdressers

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 re...

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

The Island Ch. 01

by JJ122964 on Sep 14, 2017
NonHuman

The island is a self-sustaining environment that takes care of its inhabitants and itself. All of the citizenry are male and enjoy the idealistic life running on the beach, swimming in the waters around the island, and fishing. There is a lot of sun bathing and enjoying themselves on the island. Since the weather is usually in the 60s to low 80s, there is li...

The Islander

by Lola49 on Sep 16, 2017
Mature

I saw him today as I walked along the shore enjoying a steady breeze of warm tropical air on my face, his face in shadow from the glaring sun. The sun was not kind to me... I felt as if I was baking. I had reached the half way point of my destination. He walked along the shore shoeless, shirtless in his swim trunks. I could not take my eyes off his beautiful...

Island Hiking Adventure

by FeatherFur on Aug 1, 2015
Miscellaneous

You arrive at port at around 10:30 am, all the shops in the small town are open and the firsts of the hundreds of tourists that flood the area yearly are rolling in. There are two islands to hike. The north is the larger of the two so you could easily be on your own, its more "natural" with only a few buildings, mostly at the dock but there are a...

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Welcome to pleasure Island

by talesofswamppoint on Sep 26, 2017
Fantasy

The cruise ship was steadily making its way toward a far-off island in the Caribbean. The people on the ship were anxious to arrive at the place called Pleasure Island. This all included resort was supposed to be the best place on earth to spend some vacation. It was open for single and young couple only. The resort was offering a unique experience to their...

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