Last Sailing

Daddy · Bears · Hotels · 3,578 words · 16 min read · 2026.09.25

The board in the ferry terminal flipped the six-forty to CANCELLED while I was still reading it, and a man two seats down from me said, “Well, that’s a shame,” in the voice of someone who didn’t think it was a shame at all.

I looked over. He had his boots up on his duffel and a paper cup of tea balanced on one knee, and the wind outside was throwing rain sideways against the glass so hard the whole wall hummed. He kept rolling a loose thread between two fingers, worrying it out of a hole in the cuff of his navy wool jumper, and when he turned his head I saw the grey coming in through a short dark beard. Mid-forties, I’d have said, and in no hurry about any of it.

“You’re not upset,” I said.

“I live on the island. I’m upset about once a month. You get used to it.” He tipped the cup at me. “You’re the one with the suit bag.”

I was. I had a wedding on the island on Saturday, my cousin’s, and I’d come down a day early to be useful. Now I was going to be useful from the mainland side of a two-kilometre strip of angry water.

“There’s a hotel up the hill,” he said. “The Harbourmaster. It fills fast on nights like this. If you want a room you should walk now, not after you finish feeling sorry for yourself.”

“I wasn’t feeling sorry for myself.”

“You were a bit.” He stood, and he kept standing for a while, because he was big. Not tall so much as broad, the kind of broad that comes from years of lifting things and then a few years of not bothering to stop eating like you still do. The jumper sat snug over his belly and loose everywhere else. “Warren,” he said, and put his hand out.

“Toby.”

His palm was dry and rough and very warm from the tea. He picked up his duffel and I picked up my suit bag, and we walked up the hill together in the rain because it seemed stupid not to.


The Harbourmaster was three storeys of white weatherboard with a green door and a bar on the ground floor that smelled like chips and wet coats. The woman at the desk knew Warren by name and told him she had one room left.

“Just the one,” she said, and looked at me, and looked back at him, and her face did something polite.

“Give it to him,” Warren said. “I’ll sleep on the bench at the terminal. I’ve done it before.”

“You will not,” she said. “It’s got two beds. Room nine. Top floor, end of the hall, the one with the window seat. You two work it out.”

So we worked it out by climbing the stairs. The staircase turned twice, and the carpet on the second landing was worn through to the boards in one oval patch right where everybody’s foot landed on the turn. Room nine was at the far end of the top corridor, past an ice machine that rattled and a fire door propped open with a brick. Warren unlocked it and stood aside to let me in first.

It was bigger than I’d expected. The door opened onto a short entry with the bathroom on the left, and past that the room widened out. Two single beds were lined up along the right-hand side, a little table and lamp between them. Straight ahead was the window, a deep bay with a padded seat under it, and through the glass you could see the whole harbour lit up in the rain: the terminal roof, the ferry sitting fat and dark at her mooring, the red light at the end of the breakwater going on and off. The left wall, opposite the beds, had the wardrobe and a desk with a kettle on it, and under the shelf beside them a radiator was already ticking itself warm.

“I’ll take the one by the window,” Warren said.

“Fine. I’ll take the one by the door so I can escape.”

He laughed. It was a good laugh, low and short, and it came out of his chest more than his mouth. “Smart man.”

I hung the suit bag in the wardrobe and stood there with my back to him longer than I needed to, because I’d noticed on the stairs that I kept looking at his arse and I wanted a second to tell myself to stop. When I turned round he had pulled the jumper off over his head and was standing by the window in a grey T-shirt gone thin with washing, shaking rain off the wool. His forearms were thick and furred dark. There was a tattoo of an anchor on the inside of one of them, faded to the blue of an old vein.

“Navy?” I said.

“God, no. Ferry. Twenty-two years. Engineer on that one,” he nodded out the window at the dark boat, “until my knees told me to retire. Now I fix outboards in a shed and complain about the weather.”

“So you know the captain who cancelled it.”

“I know the captain who cancelled it. She’s right. You’d have been sick in your suit bag.”

We went down to the bar because there was nothing else to do. He had a pint and I had two, and he ate my chips when I stopped eating them without asking, which should have annoyed me and didn’t. He asked what I did, and I said maths teacher, and he asked if I was bringing anyone to the wedding. I said no. He looked at me over the rim of his glass for a second longer than the question needed.

“You?” I said. “Anyone at home waiting to hear you’re stuck?”

“Just a cat. She’ll punish me tomorrow.”

I laughed, and then I stopped laughing, because his knee had come to rest against mine under the table and he wasn’t moving it. The bar was loud. I didn’t move my knee either.

“Toby,” he said, low enough that only I heard it. “I’m going to say something, and if I’ve got it wrong you tell me, and I’ll go sleep on that bench after all and we’ll never mention it.”

“You haven’t got it wrong,” I said.

He finished his pint in one long swallow. “Right,” he said. “Up we go, then.”


He kissed me on the second landing, right on the worn patch, one hand flat on the wall beside my head and the other holding my jaw like he was checking it was on straight. His beard was softer than it looked. He tasted of beer and salt from the chips. I grabbed a fistful of the back of his T-shirt and pulled, and he made a sound into my mouth that went straight down my spine and settled low in my gut.

“Not here,” he said against my lips. “Mrs Kerrigan will have my licence.”

“You don’t have a licence.”

“She’ll invent one to take off me.”

We made it past the ice machine. Outside room nine he fumbled the key and I laughed at him and he pushed me back against the door with his whole body, belly pressed to mine, and I could feel him hard through his jeans, thick and heavy against my hip. I stopped laughing. He got the door open behind me and we half fell through into the little entry, and he kicked it shut, and the lock clicked, and it was suddenly very quiet except for the rain on the bay window and the radiator ticking.

“Lights,” I said.

“Leave the lamp.”

He walked me backwards out of the entry, past the bathroom door, into the room. My calves hit the edge of the bed by the door, my bed, and he stopped there and took my face in both his hands and kissed me slower, like we had all night, which I suppose we did. His hands went down to my shirt buttons. His fingers were too big for them and he swore under his breath and I did them for him, and he watched me do it with his mouth a little open.

“Look at you,” he said. “Christ. You’ve been hiding all that under a cardigan.”

“It’s a nice cardigan.”

“It’s a terrible cardigan.” He pushed the shirt off my shoulders and put his mouth on my collarbone, then my chest, and when he found my nipple and bit it I grabbed the back of his head and heard myself say, “Fuck, Warren,” louder than I meant to.

“That’s it,” he said against my skin. “Say it like that.”

I got his T-shirt up and off, and he was exactly what I’d been imagining in the bar and on the stairs and for the last hour, if I’m honest. The barrel chest had gone soft over the muscle, the hair on it dark and shot with grey, and my palms were flat on his belly before I’d decided anything, just to feel how warm it was. He shivered when I did it. I dragged my thumbs down through the hair to where it thickened under his navel and disappeared into his jeans, and I undid his belt.

“Sit,” he said.

I sat on the edge of the bed. He stood between my knees and let me open his jeans, and I pulled them down with his briefs in one go, and his cock came up heavy and dark and fat, curving a little towards his belly, the head already wet. I looked up at him. He was watching me with his hand on my hair, not pushing, just resting there.

“Go on then,” he said. “You’ve been wanting to since the chips.”

I took him in my mouth. He was too thick to get far at first and I didn’t care; I worked the head with my tongue and my lips and my hand round the base, and he groaned and his hips rocked forward and the hand in my hair closed. “Oh, there he is,” he said, rough. “That’s it. Take a bit more for me. Little more. Fuck, look at that mouth.”

I took more. My eyes watered. He tasted of skin, and he smelled of wet wool and sweat and the rain we’d walked through, and every time I pulled back to breathe he said something filthy and kind, “that’s it, sweetheart,” and “you’re doing so good,” and “Jesus, you want it, don’t you,” and I nodded with my mouth full because I did.

He pulled me off by the hair, gently, and bent and kissed me with his cock still wet between us. “Up the bed,” he said. “Get those off.”

I toed my shoes off and shoved my trousers and underwear down and kicked them somewhere towards the wardrobe. He dragged his boots off one at a time, hopping, and stepped out of his jeans and left them in a heap by the table between the beds. The single bed was narrow and the mattress dipped hard when he knelt on it. There wasn’t room for both of us side by side, so he didn’t try; he just climbed on top, all that weight settling over me, belly on my belly, chest hair against my chest, and it was like being pinned under a warm wet-weather blanket. I wrapped my legs round the backs of his thighs and he laughed into my neck.

“Greedy,” he said.

“You started it. At the terminal.”

“I did not.”

“‘That’s a shame,'” I said, doing his voice, and he bit my shoulder hard enough that I yelped.

He reached over to the table between the beds, knocking the lamp so the light swung across the ceiling, and dug in the pocket of his jeans where they lay in their heap on the floor. He came up with his wallet and took a condom out of it and a little sachet of lube, and held them up between two fingers.

“Island man,” he said. “Always prepared for bad weather.”

“How long’s that been in there?”

“Long enough that you should be flattered.”

He settled between my legs and pushed my knees up and apart, and looked at me for long enough that my face went hot. Then he tore the sachet with his teeth and slicked two fingers and pressed one against me, slow, circling. I breathed out. He pushed in.

“Relax for me,” he said. “There you go. Christ, you’re tight. When did someone last look after you?”

“A while,” I said. “Fuck. A while.”

“Well, I’m here now.” He worked the finger in and out, then added the second, and scissored them, and crooked them, and found the place, and I arched off the bed and said something that wasn’t a word. He grinned. “There it is.”

“Warren. Please.”

“Please what?”

“Please fuck me.”

“Say it again,” he said, and pressed right on it, and I said it again, louder, and then a third time because he made me.

He rolled the condom on, and the rubber pulled tight over the fat head of him, and he slicked himself with what was left in the sachet and lined up, one big hand braced on the mattress by my ribs. He pushed. It was a lot. It was so much, the stretch of him, and I grabbed his forearm over the anchor tattoo and dug my nails in. “You’re too big,” I gasped. “Oh fuck, Warren, that is never all going in.”

“Breathe,” he said. “I’ve got you. Breathe out. That’s it. Oh, that’s it, you’re taking it, look at you taking it.”

He sank in slow, all the way, until his belly was resting on my thighs and his balls were snug against me and there wasn’t a thought left in my head. He held there. He kissed my forehead, of all places. Then he pulled back an inch and pushed in again, and again, and the narrow bed groaned and knocked against the wall, and I heard myself making a noise each time he hit the end of me, a sort of broken “ah” that I’d never heard come out of me before.

“Your cock is fucking enormous,” I said. “Oh, bloody hell.”

“You love it.”

“I love it. Keep going. You stop now and I’ll drown you in the harbour.”

He didn’t stop. He found a rhythm that was slow and deep and mean, pulling almost all the way out and then driving in with his hips so the whole weight of him came down behind it, and every time he did it the headboard hit the wall. Rain was pounding the bay window. His breath was hot on my neck and he kept talking, low and steady, “open up for me, look how well you take me, fuck, you feel so good on my cock,” until I couldn’t tell his voice from the rain.

After a while he pulled out and I actually whined at the loss, and he laughed at me and got off the bed. “Come here. This bed’s a coffin.” He took my hand and pulled me up, and my legs were shaking, and he walked me across the room to the window.

The bay seat was wide enough to kneel on. He put me there, knees on the cushion, hands flat on the cold glass, and I looked out at the whole harbour spread below us in the dark: the wet terminal roof, the black ferry he used to keep running, the red light on the breakwater blinking. My breath fogged the pane. Behind me, he pressed himself up against my back and I felt his belly against my arse and his cock sliding between my cheeks.

“Anyone could see,” I said.

“Nobody’s out in this. Nobody but the gulls.” He nudged my knees wider on the cushion. “And the gulls have seen worse.”

He pushed back in. Standing, braced behind me, he could go deeper, and he did, one hand on my hip and the other flat on the glass beside mine, his big fingers over my smaller ones. I watched our hands on the window and the harbour lights through them while he fucked me, and each thrust pushed me forward so my cheek almost touched the pane.

“Oh God,” I moaned. “Oh God, that’s deep. Harder. Fuck me harder, don’t be nice about it.”

“Wasn’t planning to be,” he grunted, and gave it to me harder.

“Look at that,” he said in my ear. “That’s my boat. Twenty-two years I looked up at this hotel from down there. Never once thought I’d be up here with a gorgeous maths teacher bent over the window seat.”

“Oh fuck, Warren, fuck, I’m going to…”

“Not yet. Hold it.”

“I can’t.”

“You can. Hold it for me.” He wrapped his hand round my cock, and squeezed the base, hard, and I sobbed and held it, and he fucked me like that for what felt like a long time, grunting now, his rhythm going ragged, his belly slapping against me, sweat dripping off his chest onto my back. “Fuck, look at you. I’m close. You want it?”

“Yes. Please. Give it to me.”

“Beg for it.”

“Please, Daddy, please come in me,” I said, and I don’t know where that came from, I’d never said that to anyone in my life, and he made a sound like I’d hit him and slammed in deep and held there, shaking, and I felt him pulse inside me through the rubber, over and over. His hand was still on me. He started to stroke, fast and rough, and I came three strokes later all over the window seat cushion and a bit of the glass, crying out so loud that I was sure the whole top floor heard it.

We stayed like that, bent over, panting. The red light on the breakwater went on and off. On and off.

“Well,” he said eventually, into my shoulder. “Mrs Kerrigan’s going to want a word about that cushion.”

I started laughing and couldn’t stop, and he had to hold me up.


The bathroom was so small my hip bumped the cracked sink when I turned round, and the shower had a plastic curtain printed with little lighthouses. He pulled the condom off and knotted it and dropped it in the bin, and ran the shower until it went hot, and we squeezed in together, which meant I was mostly standing on his feet. He washed my back with the hotel’s tiny bar of soap. He washed my hair. I let him. The water ran down through the hair on his chest and his belly and I watched it and put my hand there again, flat, just to feel him breathe.

“You’re a belly man,” he said.

“I’m a you man, apparently.”

“Apparently.” He kissed the top of my head. “Don’t say that too loud. I’ll get ideas about weddings.”

We dried off with towels the size of tea towels and went back through the entry and into the room. The bed by the door was wrecked, the sheet half off, the pillow on the floor. The window seat had a wet patch and a smear on the glass, and neither of us felt like dealing with it. His bed by the window was still made.

“Mine, then,” he said, and pulled the covers back.

It was a single bed, he was built like a bollard and I’m not exactly slight, and it should not have worked. He lay on his back and I lay half on top of him, my head on his chest, one leg over his, and it did work, somehow. His arm came round me and his hand rested on my hip. The rain was easing. I could hear it change on the glass, from a roar to a patter.

“What time’s the first sailing?” I said.

“Seven-fifteen, if she runs.”

“Will she run?”

He was quiet for a second. “Probably,” he said. “Wind’s dropping.”

“Shame,” I said.

He laughed, that short low laugh right under my ear. “Now who’s not upset.”


The seven-fifteen ran. We stood on the top deck on the way across with our coffees, not quite touching, and the water was grey and flat like it had never done anything wrong in its life. The Harbourmaster got smaller behind us. I could see the bay window on the top floor, the one at the end, and I thought about the cushion and felt my face go warm.

At the island dock he shouldered his duffel and I held my suit bag and we stood there on the wet planks while everyone else streamed round us.

“Wedding’s Saturday,” I said.

“You said.”

“I’m allowed a plus one. I said no when they asked. I could probably change that.”

He looked at me. He had a bit of foam from his coffee in his beard and I didn’t tell him.

“I’d have to find a jumper without holes in it,” he said.

“Don’t. I like the holes.”

“Then you’ll have to come and tell the cat,” he said, “why I didn’t come home last night. She won’t take it from me.” And he turned and started walking up the hill, slow on his bad knees, and after a second I followed him.