Sugar Island

I saw it advertised online, in clear black and white in the pages of an adult entertainment website. I was not sure what I was looking for, other than a release from the doldrums of a dire day to day existence. I had come out of a long-term relationship rudderless, and the seemingly endless sea of porn and unfilled promises was doing my head in. The words read out like a beacon to my cock.

Sugar Island

Within the ad, was a promise of a week of heteroflexibility. One where you would be one of many, ready to take part in a competition of sexual pleasure. I didn't know what to make of it, at first. Heteroflexible? Admittedly, that was something that ended my relationship. I had dearly wanted my ex-girlfriend to put toys in my ass and she wouldn't. I started watching bisexual porn and became intrigued by the cocks of other men. Was it going to be worth the flight to Australia and the copious bits of paperwork required? Paperwork to attain consent, which would be verbally confirmed upon arrival.

What enticed me to give up life in the cold and wet of the United Kingdom for a week on an island in Australia was not just the promise of surf, sand and sunshine. Within the advertisement was a video from the ringleader of it all. Mistress looked disarming with a cute face, yet you knew she wanted to take you to the moon in a cloud of domination. She explained she had been running Sugar Island for a few years, following a significant win in the lottery. She had heard of the desires of many men who wished to be dominated. They especially wanted to be pegged. It seems my experience was a common one -- a lot of partners were not willing to go that far, and a lot of men were worried it would make them gay somehow. I never had that worry. I mean, they put a prostate up there for a reason, right?

She stated heteroflexibility was desired as it would allow for a full range of sexual experiences one may not get from elsewhere. An open environment for play. The cost was hefty, but it covered the flights, the transfers to the island, as well as accommodation and meals. What did I have to lose? Nothing. I nervously filled out the application form, which asked a lot of questions about prior sexual experiences, sexual health and the consent forms. I expected not to hear a thing until I received an email the following day.

"Good morning, Mr Jackson,

Thanks so much for your application for Sugar Island. I am pleased to inform you that I am cordially inviting you to come along to the island for the week you have specified. I appreciate your openness about how your ex-partner did not want to peg you. I understand that and that is is part of why I run this program. Plus it is an excellent chance to explore any bisexual urges in a safe and fun environment.

Each day we wake up, have breakfast, and I encourage you to explore the rest of the island as well as the local neighbourhoods. Lunches can be provided. You need to be back on the island by four in the afternoon. We will provide a light dinner and evening activities started around seven.

If at any point, you are not comfortable with the activity that is on offer, you can withdraw before the event starts and even during. Safety is paramount.

There are some general rules of the house. Smoking is not permitted, nor are any drugs. I can make exceptions for erectile dysfunction pills, but I see you do not have a problem there. Any other prescription medication is okay. Alcohol is available, but we do limit it because of its effect on sexual performance. Masturbation is, for the most part, banned although porn can be viewed from the library I have here. You should socialise with the rest of the harem, and you may get to know them quite intimately too. I hope you leave with a sense of fulfilment and I am very much looking forward to getting to know.

Kind regards,

Mistress"

A month later, I was on a plane. I went from cold weather to a warm and humid climate, where I was greeted by a welcoming party who then ushered me to the island. I arrived quite late on Sunday evening. I was so nervous. But anyhow, there were about fourteen of us. I soon found we had come from all corners of the globe and were of varying sexualities. We got to meet the Mistress herself - she was not overly tall, and by definition, a BBW woman. She was in a t-shirt which made the points of her nipples quite visible and a short skirt along with boots. Dressed in a non-threatening way.

"Hello to my harem and welcome. You will receive a package every evening before play which will explain what the next night's action will be. In tonight's package, there will be an invitation to visit the storeroom tomorrow morning between nine and eleven. We have many strap-on dildos available, so please make a selection and note in on the sheet we have provided. You will also be able to see a selection of gags and hoods, which you will be able to use as well. Select the other options accordingly. Any questions?"

I shot my hand up.

"Mistress, I know we are competing against one another somewhat. You said we would be assessed based on sexual performance. What are we being marked on?"

"I knew you would ask, Pet Paul. Well, as you can see with tomorrow's activity, I am looking for examples of longevity. Enjoy the experience but make accommodations for your physical limits. I do not expect all my pets to perform at their best. I know the environment can be most intimidating for the unrehearsed."

"Thanks, Mistress. I can sleep a little better, knowing that."

With that, we were assigned sleeping quarters. It was like a dorm set up except a more luxurious kind. Each pod had queen size beds for four guys, as well as a television and en-suite. All our suitcases were in the room already, and I nervously went in, hoping I would get along with the other guys. We were all competing for the same prize.

"Your name was Paul, wasn't it?"

"Yeah, what's yours?"

"Nathan. English? I am actually from Australia but from Brisbane."

"Yeah I am, I come from Leeds. So how did you come to be here?"

"A dominating woman and sexual exploration with other men. I was intrigued."

"That almost sounds like me...well, I did want my ex-girlfriend to dominate me, but she would not even go near my ass. When I think about it, she was rather conservative about most things. In the end, I felt like I was not myself, so I ended it. Here I am. As for doing things with other men? I have been intrigued. I haven't done it before, but I am open to it."

"Well, with tomorrow I know there is that other option. Did you tick yes for it?"

"I did. Why, do you want me to..."

"Well, if it gets to that, perhaps yes?"

"We shall see how it goes. I am sure if we don't do it then, it will happen later. You know what, I am not feeling quite so daunted about this, but what are your plans for tomorrow?"

"Well, I would rather go view the dildos first thing and hand in my paperwork. Then take a ferry to the mainland and go fishing. Might be nice to get some peace out in the sun before the big evening."

"Do you mind if I come along?"

"Of course not!"

The other two guys in the room were relatively muted, and I guessed they were nervous. I woke up to the sound of footsteps as people were already up and about. After a shower, Nathan and I perused the stockroom with a woman assisting us, named Liza.

"As Mistress stated yesterday, what I will show you is a selection of dildos that can be used this evening."

I liken it to being a kid in a candy shop. The room was lined wall to wall of every kind of dildo you could imagine. There were short ones and large ones. A variety of colours stemming from black to rainbow. Simple rod shapes, as well as realistic cocks complete with veins. A variety of textures too, I could see some ribbed ones as well. The only other thing the woman said was to choose wisely. "I have seen many men, especially younger ones, come in here and take the biggest one possible. If you are in any way new to anal pleasure, my advice is to take something a bit smaller. But it is entirely up to you". My mind kept drifting off, wishing I could experience them all. We were not allowed to touch them, but the materials were ranging from flexible to hard -- there were dildos even made of glass. But from the get-go, I made my choice clear. There was a seven-inch silicone one in fire engine red that was a bit phallic but not quite. I also opted for a cock gag. I ticked the other boxes and went out of the room, nervously excited. Nathan and I did end up spending the afternoon hiring a boat and doing a bit of fishing.

I do not remember dinner. Next thing I know, we were told to show and to come into the living room nude.

"Oh my god...this is more intimidating than I thought."

A moment hit me when I realised I was not holed up in an office back home in England. The air was warm and humid, ripe with a certain kind of something. I quickly glanced around the room. We were arranged in a semicircle, naked. I saw cocks in various states of erection. I glanced down at my own cock, and it was stirring. What on earth have I gotten myself in for?

Suddenly the din stopped, as she strode out of her room, decked in a red latex catsuit that let her tits out. I could see the black leather harness around her waist. I became twitchy. In front of me, was a black box containing a bottle of lube, a pair of gloves and condoms. Mistress was not alone, she had an assistant who was also dressed in latex. She had with her, a carry case full of the delights of anal play. A menagerie of dildos of all shapes and sizes.

"Greetings to you, my pets. Welcome to Sugar Island. Today will be the first of a set of challenges. You will compete for sexual performance and the chance to become the top pet, which gains special privileges. I will reiterate the rules. If at any moment, you are not comfortable, please speak up. If you are too aroused, you know what to do however you must be able to cum for me when it is your turn...otherwise, I will cage your cock for the rest of the week."

Shit. I guess it was not just sexual performance Mistress was after, but sexual stamina too. There was only so much training one could do beforehand.

Music started playing in the background as Mistress approached the first of the harem. We all watched in anticipation, as she started talking to the first pet. He had opted for a hood to blind him and decided he would not be jacked off. The dildo of selection was a rather huge black one. My mouth went dry. We were all transfixed. She was speaking to him in dulcet tones and telling him all would be okay. Reiterating the safety procedures. He chose to stick his ass in the air. The assistant handed Mistress the lube which she squirted in his ass hole before massaging his rim with her gloved fingers. He started to groan.

Well, if someone had been flaccid in that room before then, it was surely not the case now. Mistress slowly eased the big boy into his ass and paused for a moment.

"Keep fucking me, Miss.

"Very well then, Pet Michael."

She started to ram him in the ass hard. His balls made an audible slap, and he became vocal. It was intense, and he did not last long. Two minutes. She didn't even touch his cock.

"Oh, dear, Pet Michael. I was hoping you would last a little longer, given you are well experienced in being pegged."

She continued along the line. The air was ripe with the smell of cum and latex. Sonorous squelches and orgasms from deep within. I was taken aback by some of the dildo selections. I looked down, and I was dripping pre-cum already. Fuck it, I was so horny already. I looked to the other side of the room, and there was my roommate Nathan. He had been looking at me too. I noticed a couple of guys had left their posts to engage in a blow job in full view of everyone else. I couldn't take it.

"Do you want to..."

"Fuck, yes, I do."

I was not sure who was going to go where but I saw Nathan coming across to my table. Next thing I know, he was on his knees, touching my cock.

"Keep doing that."

I closed my eyes for a minute and felt the deliciousness of a velvet tongue wrapping around my shaft. The slightest bit of pressure as I could feel Nathan's hand having a hard grip on my girth. I wondered if he could feel the pulsating I could imagine. I went into his mouth. I hoped he enjoyed the saltiness of it and his hand went to massage my balls. "My ass...". Nathan took the lube from the black box and lubed up a finger...he then penetrated my ass hole while continuing to whiplash his tongue around my dick. Next thing I know, I jerked forward and splat. Thick, white, sticky cum all over his mouth. It was the first time a man had ever given me a blow job. There were also wet wipes available which I then used to wipe him down. We giggled. He returned to his post.

I became anxious. I knew it would be at least another hour before I would be called upon. There was no silence, just the sound of orgasm after orgasm and laughter. I was staring off into the distance when there was a tap on my shoulder.

"Pet Paul. Hello! I see you enjoyed yourself with Pet Nathan before, do you think you could perform for me?"

"Yes, Mistress"

"I got to say, I was rather looking forward to fucking your ass. You picked a good dildo there, it happens to be a favourite of mine. My very first pet I fucked...he opted for that one too. Now let me just confirm with you. Red dildo, you want to be on your back, you want to be jerked off, and you want to be gagged. Is that correct?"

"Yes, Mistress."

"Fantastic, I will just get my assistant Liza to fit you with the gag you selected. I will then get you to lie down on the table with your knees up. What I will do first is making sure your anus is well lubed. I will get Liza to do for that as I need to keep my gloves clean for wanking you off."

Her words alone made me start to leak pre-cum again. Liza was the same woman who had been in the storeroom. The first thing she did was fit Mistress with the dildo. What a magnificent dildo it was too, shiny and red with a bulbous head. She took the gag from her case and told me to open wide. In slipped a small rubber cock gag. My cock, which had been somewhat flaccid before then suddenly popped. It elicited a giggle from Liza as she buckled the gag into place. I moved onto the table, flat on my back with my knees up and legs apart. I heard the ping of rubber gloves as she slipped two lubed fingers into my ass. I don't think I could have been any harder.

Mistress was poised. She quickly fondled my balls and sweet-talked to me. I could feel the tip of the dildo teasing my ass hole and I so desperately wanted to tell her to just fuck me. Patience was rewarded as she slowly guided the dildo up my ass hole. Sweat started to form on my chest. Her hips bucked as I felt my ass tighten on the dildo, which was rubbing against my prostate. Meanwhile, her hand, clad in long black latex gloves, held my cock tight, maintaining an erection. Whispers were made as I heard the squirt of yet more lube on her hands.

The cold, wet stickiness of the lube momentarily cooled me down. I needed it. I wanted to maintain speed. So far, the guys were lucky if they lasted five minutes. A hand firmly grasped my throbbing cock and glided towards my balls. Nipples were pinched. The combination of slippery rubber and the warming of the lubrication sent me into the heavens. I started to moan loudly despite the fact I was drooling like crazy. Jerking me off, fucking me hard. I tried so hard to relent, but after ten minutes, I could not hold on any more. The table rattled, as my ass clenched down on her so she could not move and I shot hot sticky cum all over her gloves. She giggled.

No words were to be said. The gloves were removed, and I was wiped down. I watched as they picked up their gear and continued along the line. I spent the rest of the time, lightly touching my cock and realising life would never be the same again.

Two hours later, it was done and dusted. All fourteen of us were lined up in a line as Mistress walked along, this time sporting white latex gloves. Visually inspecting the limp cocks of her pets. No words exchanged.

"Well, done, Pets. It took us two hours and fifteen minutes today. I based scores not only on performance but your eagerness to experience everything. I do have my top pet selected. Congratulations, Pet Paul. The runner-up is Pet Nathan. Well, done. Your cocks and asses did you proud. Tomorrow night you will be invited into my den for playtime. As for the rest of you, you will spend tomorrow night watching a pornographic film and jacking off in front of one another. Good night."

Nathan and I were giddily excited. It had been a fantastic experience, and I was definitely looking forward to spending time with the Mistress and Nathan the following night. I was exhausted, but I admit, I felt a bit special, and so did Nathan. We shared Cheshire Cat smiles on the way back to our room, and once we got back there, we were whispering in the dark.

"Can you believe we just did that? I can't. I never in a million years imagined I would suck another man's cock in front of others. But it was not like the other guys were paying attention. Fucking hell, talk about hedonistic."

"I know. I cannot believe it either. I am feeling a lot better about tomorrow. Did the rest all cum when they had their turn?"

"Yes. There was one guy who I seriously thought was going to overtake us, but he just managed to eke out an orgasm. Mistress seems to have her ways and means, and I do wonder what she has in store for us tomorrow. Do we get to sleep in the same bed with her?"

"I hope so, but is it big enough for three people?"

"Anything is possible, Paul. Think best we kip now."

The following morning I woke up, fresh as a daisy. It was a day to take it easy. So Nathan and I ended up catching a ferry to the mainland and headed for a golf course. Being Australia and during the spring, it was not too hot, and the outdoors was the best place to be. It turns out at least half the other guys had the same plan as us. We best distract ourselves. In a way, it was two-sided. As much I liked knowing I had plans in the evening, I was a little jealous of the freedom the rest of the harem had. They could get a bit drunk, watch films, play with one another. But I definitely think my option was best. I adored Mistress already. She may have been a femdom, but you knew deep down she was holding onto a secret and seemed kinder than I could have imagined.

Dinner ended up being a barbecue, which I indulged in with relish. Mistress had dressed down and joined us outside for the meal and was clearly checking out the talent who were making full use of the pool. She kept shooting me knowing glances and I could feel a tent rise in my pants. Nathan kept blushing. A couple of hours later and Nathan and I took a shower in our room.

It was time to open the package regarding that night's activities. It required another dildo selection as well as for instructions to dress in a bathrobe and knock at Mistress's door at 8:30 p.m. With some intimidation, we headed towards the bedroom and meekly knocked.

"Pets, you may come in."

There she was, resplendent in a set of red lace lingerie. It shook my inner core a bit.

"Mistress, I was expecting you to wear something more like you did last night."

"Pet Nathan, wearing latex is rather difficult. If I am not wearing that, I prefer lacy, pretty things like this. Do you like it?"

"I rather do, Miss."

"Good, I am not always as harsh as the pets think I am. I am not really into punishment or pain. Other mistresses can do that. Not me, though."

"You are right, Mistress. I was so scared of you at first. But you are nothing to be scared of."

"I am not. So, Pet Paul, I trust you made a decision with what toy to go with this time. Something different, I hope."