The guillotine on Santamos Island (TS-male themes)


An impoverished Caribbean island nation nears bankruptcy.  In order to raise cash income from “tourists”, the nation’s leaders in desperation pass a law — consensual executions of sane and un-coerced foreigners by other foreigners will be legal in public execution areas on the island.

 I shove the toy hard up my lady-boy ass, cupping my balls and stroking my cock. My nipples are hard as I find myself fantasizing again. Then I lie back on my bed and close my eyes, picturing the blade hovering above me. It hangs there tantalizingly, toying with me with its message of instant death.

In my mind the blade suddenly releases, severing my head with one quick stroke. I thrust the toy hard up my ass as I furiously stroke my cock to the terribly erotic image. Cum spurts out of my throbbing dick and coats my tits as I shudder from a wonderful release.

If Jason were here he would be taking my ass himself. But he’s off to buy tickets for Santamos Island – the island of consensual executions. I slowly thrust the toy in and out of my ass in the afterglow of a wonderful release as I gently stroke my softening she-male cock.

I’ve had this fantasy for as long as I can remember. But it’s only been a few weeks since I learned of the existence of Santamos Island. How I managed to convince Jason to go buy tickets for the two of us is still a mystery. Perhaps it’s because he’ll be getting all my worldly possessions and my bank accounts after I’m gone.

I met Jason by accident after going through a bad breakup. He was kind and thoughtful, and we hit it off right away. It didn’t take long before I wanted our relationship to become sexual. But I was afraid of his reaction to me.

One day he told me he wanted to go swimming with me. I told him I would love to but that I was afraid of his reaction because I had a little ‘something extra’. When I came out in my bikini I took his hand and placed it on the bulge in my crotch.

His eyes widened in surprise and he gave me this funny look. “Oh really?” he said to me. “Interesting.” Then I’ll be damned if he didn’t start rubbing me until I started getting hard!

Well you can imagine what happened after that. I was so relieved as the two of us started making out right there in the pool. We went underwater and started bubbling, kissing and caressing each other until I was boiling over.

From there we ended up in a hot tub where our suits quickly came off. I ended up giving him an underwater blowjob and he returned the favor. From there we rapidly became fuck-buddies. He even let me fuck his ass.

It took a couple months before I finally shared with him my guillotine fantasies. He thought it was weird at first. But I told him it made me so hot, especially now that I had begun imagining him as my executioner. It took him a couple weeks but he actually came around, especially because he liked pleasing me.

The hottest night of my life was the night he decided to try to come up with something similar for me to experience. He wasn’t the least bit interested in removing my head. But he did come up with something that added to the fantasy.

He blindfolded me and then started fucking me on the bed. Then he put some sort of thin rope around my neck. “This should simulate the blade coming in contact with your neck,” he told me. Then at the count of three he rammed his cock hard inside me while jerking the rope tight around my neck.

Gawd; that did it! It wasn’t a blade or anything, but it felt like something wanted to cut into my neck. I came so hard that my cock erupted until cum spewed all over the two of us. I felt him cum up my ass a few seconds later.

Fuck; what inspiration! I fucking loved it! We began playing like that for a while, being careful with what we used so that it didn’t strangle me too much.

Things changed when I discovered the existence of Santamos Island. I told Jason I wanted him to take me there and make me ride the guillotine while he was fucking me. He told me he wasn’t the least bit interested in watching me die.

I wore him down until I finally proclaimed that if he didn’t take me, I would find someone else who would. But I told him my greatest fantasy was for him to be there fucking me when it happened. I even told him I would find a way so that he wouldn’t have to actually be the one to execute me if that would make it easier on him.

Can you believe it? He reluctantly agreed. And today he’s buying the tickets to fly us out tomorrow.

When he comes home with the tickets I plant a big, juicy kiss on those sweet lips of his. Then we fuck like bunnies for the rest of the day. Later that night we collapse into bed totally exhausted. But I cannot sleep. My mind swirls with what it will feel like when my neck finally meets the blade.

The next morning I dress in my absolute sluttiest. Then we head for the airport. I take nothing else with me, for I plan on being dead by nightfall.

When we arrive, we check in right away to the Robespierre Hotel. It has a full-sized guillotine right out in front where everyone can watch. My lady-boy cock is hard and ends up dripping for the rest of the day… the rest of the day which also happens to coincide with the remainder of my lifespan.

We take a tour of the island and get to witness an execution over at the rifle range. Then we walk down to the beach and catch a man and woman tied to the tidal stakes. Every now and then the gallows claims another life. We even get to watch a beheading by axe.

I’m so turned on I can hardly stand myself. I can’t believe this place! This island actually exists! People are being executed all around us, and I’ll soon be joining them.

Jason is contemplative as we spend our last dinner together. I tell him how deeply I love him and how much all this means to me. Then I suggest he find some nice piece of ass to fuck after I’m executed. After all, I don’t want him to be alone for too long after my beheading.

I desperately want to fuck right after our last meal together. So does Jason. But I ask him if we can hold off. I tell him I think it will be so hot if we allow the excitement of my approaching execution to build so that our last fuck together turns out to be our best fuck ever. He reluctantly agrees.

After dinner we go for another walk. We witness another couple of beheadings by axe, both of whom are females. I can tell it is having an effect on Jason, and I find myself hoping he comes so very hard in my ass once the blade severs my head from my shoulders.

We deliberately avoid the guillotine until the sun goes down. Now it seems as though I don’t want to see where I’m going to die until it’s time. We make our way back to the Robespierre, going in through another entrance.

We sit in the lobby sipping brandies as the time grows short. Then I look over at him, my body trembling like crazy. I suddenly have reservations about the whole damned thing. But I’m not backing out. Arrangements have already been made for Jason to take possession of my things back home.

We walk up to the hotel concierge and sign the requisite forms. Then we head outside to the waiting guillotine. There is no one around; we have arrived during a lull in the executions.

The tension is palpable as we kiss while he slowly disrobes me. My breath catches in my throat, and I begin to tremble like mad. “Are you sure you don’t want to back out?” he asks softly.

In response I show him the paperwork. “The papers have already been signed, baby. I’m going through with this one way or the other. Now strap me down and make love to me. Just leave my arms free.”

He does as I ask, and we begin caressing each other until I lie down upon the bench. He straps me down before locking my head into the lunette, making sure I can caress him with my hands. Then he sucks my lady-boy cock, allowing me to feel it in his mouth one last time.

He kisses, suckles and caresses my heaving tits as I look up at the blade. Then he places his cock in between them, pressing them together with his hands and fucking my breasts. I whimper and moan, rock hard with excitement as I stare at the blade hovering above me.

I tell him to give me the rope to the blade and I will do it myself as he cums. But Jason says, “Not yet.” Then he enters my ass where he gives me the longest, best fuck of my life.

When he finally cums, I feel his hot seed deep inside me. He comes around and kisses my lips. Are those tears in his eyes? Then he hands me the rope as he tells me, “My dear, I will be the one to feel you cum inside me when the blade falls.”

He goes back around and straddles me, impaling his ass upon my hard, quivering she-male cock. Then he starts rocking as he gropes my tits. Suddenly I’m so damned scared – and yet so fucking excited – that I can hardly think straight.

I hold the rope in my hand… literally hold my life in my hand. I maintain my grip on it as I thrust up into his ass, his muscles clenching around my quivering shaft. His hands grope my boobs, and I’m filled with a terrible fire of arousal.

I suddenly notice quiet voices all around us. People have wandered over to have a look. My execution will not be private after all.

I’m turned on even more as I hear snippets of conversation… “She must be a she-male; he’s riding her cock…”  “Gawd; they’re making love to each other! That is so fucking hot…”  “Do you see that? She’s holding the rope in her hand! Gawd; she’s actually going to execute herself…” “I’ve never seen a beheading quite like this one! They must really love each other…” ”Look at the way he’s riding her! See how hard his cock is? Gawd; I’ll bet they both cum when the blade drops…”

We build up to an eager, anxious fuck, my lady-boy cock driving hard up inside him as he rides me. That’s when I feel it start to swell inside me. Gawd; I’ve really got to do this right now or I’ll go crazy…


I don’t know when I let go of the rope. All I know is that I actually hear the blade hit the bottom… hear the gasp from the crowd. Then I’m looking at wicker all around me as my head lands in the basket.

I hear Jason call out for someone to retrieve my head. I’m lifted up out of the basket and handed over to him. I’m given an extraordinary view of my body as it jerks and spasms underneath him. Gawd; that is such an incredible sight!

He cries out in orgasm, his cock spewing another load upon my quivering tits. I can feel nothing below my neck now. I can only hope I came inside his ass when the blade dropped as my last present to him. Then my vision starts to fade.

The last thing I see is his face… the last thing I taste is his lips upon mine as he kisses me tenderly. Then my vision fades completely. I happily settle into oblivion, my fantasy fulfilled at long last…

© 2012 (written June 5 ’12 by riwa)

(Original idea for the Island of Consensual Executions created by Arachnid.)

How useful was this post?

Click on a star to rate it!

Average rating 3 / 5. Vote count: 2

No votes so far! Be the first to rate this post.

This entry was posted in Beheading Stories, Male stories and tagged , , , , . Bookmark the permalink.

Leave a Reply