The Island Ch. 01 – Anal – Sex Story

I pulled back on the throttle until the engines were just a soft warble. The ten-meter-long blue and white RIB slowed and glided towards the mouth of the harbour. The small waves caused by the light breeze glittered in the sun, and above the squawking of the birds had people already pointing their binoculars skyward.

The boat rolled as she slowed and I glanced down at the nine passengers sitting in front of me. All of their attention was focused outwards at the island and the wildlife. Those that weren’t looking up at the birds were scanning the water for seals.

I had been driving the nature cruise boat for a month now, a temporary job that was becoming permanent as spring gave way to summer. I pushed forward on the stiff throttles and the boat chugged ahead through a small opening in the rocks. A hundred meters further in a rudimentary wooden jetty was visible sticking out from the white sand beach.

The tiny harbour at all times entertained me, you could never see it coming and it looked like you were sailing straight into the boulders until the last minute when the entrance came into view.

The island we were visiting wasn’t big, you could walk around it in a couple of hours. That was very much the company model. The business I worked for ran the boats out of a port on the mainland, bringing sightseers out and leaving them to explore for a few hours before shuttling them back. In the summer we made the fifteen-minute trip out at least a couple of times per day.

I slowed the boat again as we approached the jetty. A couple of figures walked out along it from the beach. The jetty had been there for as long as any of the current visitors had been alive so I was at all times very careful to put the minimum pressure on it as the boat came alongside, for fear that it wouldn’t be there much longer.

A few birds squawked and flew up as we cruised the last couple of meters. As I kicked the engines astern to stop her, the two girls who had walked out reached down with boat hooks to catch the lines coiled on the boat’s bow and stern. They quickly pulled the lines tight and cleated them off on small bollards attached to the jetty, in a manoeuvre that was practised many times each week.

‘Welcome’ I said to the passengers, killing the engines as soon as the lines were secured so that I didn’t have to shout. ‘Take it steady as you step off the boat, one at a time. I don’t want to have to fish anyone out of the sea.’ There were the usual smiles and slowly people filed off the boat. ‘This is Sarah and Dee.’ I said indicating the two girls as they smiled and waved. ‘They’ll just give you a quick chat about the do’s and don’ts around the island and then Dee will go with you and I’ll see you back here at 3 o’clock.’

Sarah smiled at me and launched into her usual spiel as I climbed back around to the helm of the boat. I made a couple of notes in the log about arrivals and passenger numbers and shut the electronics off. The boat would stay here until I came to take the passengers back in at the end of the trip, and I didn’t want the batteries going flat. In the outer reaches of the harbour, a seal stuck its head up and swum in lazy circles in the sun.

I sat back in the helm seat and subtly stared at Sarah from behind the cover of my polarised sunglasses. She at all times looked fit but the particularly sunny day had given her an excuse to wear some especially short shorts and a tank top. Her blonde hair was plaited back in a ponytail and her brilliant blue eyes were also hidden behind shades. She was a manager for the nature trust that owned the island, with Dee as an assistant. The two of them lived there over the course of the summer managing the stream of tourists from boats like mine. Despite the weather, we were the only boat in today as it was the middle of the week and the schools were yet to break up.

I noticed her head angled towards mine as she finished speaking and Dee took over. I moved on to tidying up the lines as Dee led the group away onto the island. As usual, Sarah had stayed behind to chat. The first few time’s I’d visited we’d had stilted conversations about the boat, the island and the weather, but as I’d visited more the conversations had become noticeably more forward and flirty. The boat rolled and I looked up as she stepped on board.

‘Afternoon.’ she said, sitting on the rail.

‘Hey, how’s your day going?’

‘Good… were you checking me out while I was talking to your clients?’

‘No.’ I replied, probably slightly too quickly. She smirked and laughed as if she was joking.

‘How’s the boat?’

‘Fine, I serviced the engines after yesterday’s trip and they are running sweet now.’

‘Oh, good with your hands are you?’ I held her gaze.

‘I have my moments.’

‘Well, if you are just gonna be sitting around here as usual, waiting for the guests to get back you can come and have a look at our quad bike we use to drag the stores up to the house. It’s not working.’

‘Sure, but what do I get in return?’ I asked.

‘I’ll think of something…’ she said, smiling at me and standing up.

‘It’s inside the hut at the top of the path by our accommodation.’ She stepped off the boat. ‘If you can have a look this afternoon I’d really appreciate it. Only if you have the time obviously.’

‘I’ll see what I can do.’ I said. She laughed.

‘I’m sure you will.’ She headed down the jetty towards the path up to the hut. It was all I could do to avoid following her immediately. Only a desire to play it cool coupled with the sudden need to conceal a semi, forced me to remain on the boat. I watched her ass until I lost sight of her, I couldn’t fathom the need for shorts that high, but I certainly wasn’t complaining.

I killed fifteen minutes pretending to inflate the rib’s tubes before grabbing my box of tools from one of the lockers and following her up the path.

I arrived at the wooden storage hut to discover the door open and Sarah sat on the quad. There was no lighting in the shed, but it wasn’t a big space, probably enough to fit another bike in at a push, but they only had one. The sunlight flooded in from outside through the open door but also filtered through the gaps in the planks of the hut’s walls.

‘You took your time.’ She said.

‘What’s up with it?’ I asked, ignoring the jibe.

‘If I knew that, I wouldn’t need you would I?’ She swung her long legs off the bike and moved over to me.

‘I’ve had a poke around the engine.’ She said, bending over directly in front of me to look more closely at the bike, but I can not see anything wrong.’ I tried desperately not to notice the way the shorts hugged her ass, inches from my hips. There was no way she was doing that accidentally, I wondered. I knelt down next to her, doing my best to keep my focus on the bike.

‘Errr well does it fire when you turn the ignition?’ I asked.

‘Nothing’ She said

‘Show me.’ She stood up and swung her leg over the bike, leaving me crouched down by her knees. She flicked the electric begin and nothing happened, just a dead click, the engine didn’t even try to turn over.

It sounded like the battery wasn’t even connected, I wondered. Then I began to wonder… I stood up and moved around to the back of the bike. Sarah slipped off and stood next to me. I flipped the seat to reveal the battery and saw the isolator had been turned off.

‘I think that might be the issue’ I said. ‘It’s strange, someone would have to turn that off for it to fail.’ Sarah took a step closer to me and peered in.

‘Strange’ she said, ‘I can not imagine how that would have happened! Well, thanks anyway. I guess I was right, you are good with your hands.’ I tried to laugh but it sounded a bit forced.

‘Well, you are welcome, so unless you want help with anything else…’

‘What did you have in mind’

‘Oh, nothing.’ I realised she was still stood unnecessarily close to me. I stepped back slightly and went to move around her.

‘Well, actually there is one thing.’ She said. ‘But it might be a bit more involved.’ She was staring me straight in the eyes again.

‘Oh?’ I said.

‘Close the doors if you want to figure out.’ I pretended to think about it for a second before stepping around her to the double doors and pulling them closed. I turned back to face her in the semi-darkness.

‘I’ve been stuck here for weeks.’ She said. ‘Everyone has access to Lovehoney but I’m missing the real thing.’

I felt like I was in a dream, surely this couldn’t be happening. I glanced around wondering if there was any feasible way I could have misunderstood what she was asking for.

‘Don’t pretend I haven’t caught you staring.’

‘I haven’t…’ I started

‘So we both want each other, and right now I really need to be fucked.’ I could feel my cock pressing against my shorts, and I’m sure she could see it as well.

‘Here?’ I asked

‘Unless you’ve got to get back to the boat…’ She moved forward and I stepped to meet her. Our mouths met and I felt myself throbbing against my shorts. We kissed hard, her tongue finding its way inside my mouth and swirling over mine. I reached down and squeezed her ass through the tiny shorts, pulling her against me. She moaned as our hips ground against each other and I broke off the kiss to bite her neck. She moaned louder and I took that as a sign that she was into it.

I continued to bite up her neckline towards her ear, we were both breathing harder and she reached down to rub my cock through the fabric of my shorts. I traced the curves of her ass with my fingertips through the thing fabric. Fuck, I wanted her so badly.

‘You’re ready then.’ She smiled at me.

Fuck yes.’ I laughed

‘There’s one catch’ she said. I raised my eyebrows but given everything that had happened I should have expected something.

‘Go on.’ I said, squeezing her cheeks through her shorts again. She moaned a little more.

‘I don’t have any condoms, and I’m not on the pill. So unless you’ve got some on that boat…’

My face fell, I knew it was too good to be true. She must have caught my expression change.

‘Thankfully there is one solution I can think of…’ she smirked. ‘Have you done anal before?’

My mouth must have fallen open slightly because she smirked again and it took me an extra beat to respond.

‘Um, yeah I had a girlfriend at uni who was into it.’

‘Well it won’t be something new for either of us then.’ she said. She let go of me and pulled my t-shirt up over my head. I was still a little surprised and just went along with it. She ran her hands down my chest and I was suddenly thankful for all the hours I’d spent moving heavy boats around the yard. I enjoyed the way her soft hands ran down my pecs and traced down my abs. I thought how long she had been planning this for as she hooked her fingers inside the waistband of my shorts, causing me to give an involuntary shiver of anticipation.

I reached up and pulled her top over her head to reveal a skinny sky-blue sports bra beneath. Her boobs looked large against her athletic body. I could see her hard nipples pushing against the material. She stepped back and grabbed something from a backpack led behind the quad. She passed it to me and I looked down to see a tube of lube.

‘I would have put money on you being up for it so I came prepared.’ She said. I pulled my shorts and boxers down, freeing my aching cock and she turned around to lean over against the quad. I could see the toned muscles in her back clearly defined as she put her weight forward onto her arms. She was breathing quickly and I could tell she wanted it much as I did. I stepped behind her and slowly pulled her shorts down. I enjoyed each moment as more of her perfectly smooth ass was revealed to me. Despite her athletic create, her ass curved beautifully, accentuated by the way she was bent over. She wasn’t wearing any underwear.

‘Well, that’s a nice surprise.’ I said.

She jiggled her ass up and down, bouncing on her tiptoes, I could see she was soaking wet already. ‘Please, I need it so badly.’ She said.

I took a chance and slapped my free hand down on her ass, hard enough to leave a mark.

Fuck.’ she said, drawing a sharp intake of breath. ‘I had a feeling you were gonna be good.’

‘Patience.’ I said. I dropped my boxers and stepped being her, squeezing lube onto my cock as I did.

‘Don’t be gentle.’ she said ‘I’m a bad girl and I should be treated like one.’

I grabbed hold of her ponytail and pushed her head down, bending her further onto the quad. She moaned and arched her back.

‘Be careful what you wish for.’ I said. I squeezed lube on the top of her ass and watched mesmerised as it slowly dripped down her tight bud. She squirmed slightly as it ran down. I gave her another firm slap on the ass and she whimpered again.

‘Be a good girl and stay still.’ I said.

With one hand still holding onto the ponytail, I ran the fingers of my free hand gently over her puckered bud. She groaned loudly as they grazed over her, and pushed back slightly.

‘Who knew you were such a little slut, Sarah?’ I said and she giggled.

I spanked her ass again before starting to push firmly as I massed around her asshole in small circles. She’d started to pant and her hips were pushing back against my fingers harder. I squeezed some more lube onto my fingers and slowly pushed my index finger into her arse. She whimpered again but pushed back. She was incredibly tight as I slid into her, one joint at a time. I could feel her gripping me as the lube allowed me to keep sliding inside.

I slowly started to work my finger in and out of her arse enjoying the quiet sounds of pleasure she made as I did so. ‘Please, I can take more.’ She said.

I squeezed a bit more lube onto my fingers and pushed my index and middle finger in together. She groaned and arched her back as they started to go in. I had to push harder this time and she gripped the quad holding herself still as they went in. She was tight but they slipped inside. Gradually I pushed them further and harder into her, finger fucking her ass over the bike. She’d slipped one of her hand’s hands underneath her and was masturbating hard as I did so.

I stared as her fingers flicked over clit, clearly pushing forcefully against herself. I could see her knees shaking slightly as she moved faster.

‘Fuck, I’m getting close.’ She said. ‘Please, I want to come with you inside me.’ I needed no further asking and slathered more lube onto my cock. She was still firmly playing with herself as I pushed the head of my dick against her asshole.

I pushed into her slowly and she let out a long moan. I was barely a couple of inches inside her when she started saying ‘Fuck, you are big, are you nearly there yet?’

‘Nearly.’ I lied and kept slowly pushing into her. I could feel her tensing and the way her warm ass gripped my cock was unbelievable. I reached forward to hold onto her shoulders as I continued to push deeper. Her legs shook noticeably and I could hear her taking deep breaths as she stretched to accommodate me.

‘Good girl, you can take it.’ I said.

‘Oh my god, oh my god, oh my god.’ she kept repeating as my hips pushed against her butt. I was fully inside her as and I could feel her fingers tickling against my balls as she continued to masturbate underneath me.

‘Good girl, that’s all of it.’ I said and slowly began to thrust in and out of her. I could feel the head of my dick being squeezed inside her in the most delightful way. An electric excitement ran through me as I drew my hips back until I was almost out of her before pushing balls deep into her again.

Her hand flicked backwards and forwards over her clit as she gripped the seat of the bike hard enough for her fingers to go white in the other hand. I took hold of her ponytail in one hand, pulling her head back with her hair, making sure I was as deep inside of her as I could be as our hips came together. I let go and she slumped forward onto the bike moaning constantly now.

I gripped her hips in my hands and picked up the pace.

‘Oh fuck.’ she kept repeating.

My dick continued to slide in and out of her tight arse, with each thrust I tried to move further inside of her. Her ass cheeks clapped into my thighs as we came together adding to the red colour from my hand earlier.

‘Ah fuck, I’m gonna come.’ She said

I gripped her hips hard as she shook beneath me. ‘Ah fuck, ah, ah fuck’ she groaned as she went limp against the bike. I wondered about slowing down, but then I wondered about the teasing and the fact she’d lured me here and decided I needed to have my own fun as well. I continued to pound in and out of her, the bike and my grip on her hips holding her up.

‘Oh fuck, I’m not sure I can take this much more.’ She whimpered. I kept fucking her continuing at the same pace as before. I could feel my orgasm building in my balls.

‘Good girl, you can take it.’ I said.

She was moaning constantly now ‘Fuck, I’m gonna cum again.’ She said.

‘I’m fucking close.’ I said, panting for breath. The way her arse gripped my dick as I pumped into her felt incredible, she was so tight but so perfect at the same time.

‘I want you to cum in my mouth.’ She said. I didn’t need to be told twice.

‘Ok when I pull out, turn around and my dick is going down your throat.’ The wondered of it pushed me closer to the edge.

‘Oh, fuck yes.’ She said

She groaned and arched her back as she came. It pushed me to the point of no return and I felt my balls tighten as my orgasm built. I pulled out of her and stepped back. She quickly turned around and knelt in front of me, her gorgeous mouth open wide and her tongue sticking out.

I immediately pushed into her mouth. Her hands reached up and gripped my hips pulling me further in, holding me there despite the fact she gagged against me. I came hard, my thighs twitching as I shot cum down her throat. She stared up at me, her eyes watering but still holding me deep inside. I could have stayed there forever but eventually, she pulled her head back and slowly began licking the last of my cum off the head of my dick. I couldn’t speak for a while I just stood there trying to comprehend what had just happened and let my heart rate return to typical.

After both our breathing had slowed she kissed the tip of my dick and stood up. ‘Well, that was as fun as I had imagined.’ She said.

‘Erm, yeah.’ Was all I could manage, my balls still ached from how hard I’d just cum. ‘You were fucking incredible.’

We retrieved our clothes from spread around the shed. I checked my watch. Shit, how had the time gone so quickly? The guests would be back from exploring the island soon. I was gonna struggle to make everything appear typical after the experience I’d just had.

Sarah pulled her top on and made her way to the doors and opened them, letting light flood back into the shed.

‘This is gonna be a fun summer, how many time’s are you gonna be over next week?’ She asked.

‘At least three.’ I replied, ‘But that’s only gonna increase as things get busier.’

‘I think we might need to get some more lube then.’ She said walking outside and leaving me standing there. I was still processing everything that had just happened but I couldn’t help but feel this was gonna be an entertaining season. I checked around to make sure I hadn’t left anything and then made my way back down to the boat.

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