15. Jamie

The sound of wind and rain lashing the window wakes me from a dream of lazing in a hammock, the gentle sway mimicking the rocking of the ship. In my dream, Teddy was laying on top of me, and he's doing the same in real life.

Pleasantly warm and comfortable, I hate to move, but I can't ignore my bladder. Teddy's snores falter when I slip out from under him, but he doesn't wake. The sun hasn't risen yet, and we're still moored on Cock Island as the storm rages outside. They announced that all decks were closed shortly before we fell asleep, so we'd stayed in.

We talked last night about going further, but I could tell Teddy was having choice paralysis. He said it was up to me if I wanted to go further, and I wanted to try. I could wait until we are back home on our own, but I can't help feeling like the spell will be broken once we leave.

The thing is, I know my best friend like I know my own mind, and he is ignoring his normal subconscious guilt trip. It will kick in when we get back from the trip and he'll beeline for the nearest priest to confess, just like he does after all our vacations and frat parties when he thinks he's somehow angered his religion by enjoying himself.

While I understand to some extent—Catholics don't have a monopoly on guilt—I also see how free he is being. Teddy needs to let himself enjoy life more, and I tend to be the only one who helps him do that. Premarital sex is against both our religions, but neither of us is devout or strict about following the rules, either.

Hopping in the shower, I use the attachment I bought at the onboard shop when Teddy thought I was grabbing more sunscreen and try douching for the first time. It feels weird and not at all the turn on my finger was, but I'm more confident in approaching Teddy to try this whole butt sex thing with me.

The thought makes me chuckle as I dry off and brush my teeth before lubing a finger with the bottle provided by the cruise line and slicking my hole. It feels good enough for me to add a second finger before I make myself stop. Yeah, I am into this and find myself shivering in anticipation. I set the lube on the nightstand and get out a condom from the drawer where I saw an assortment before.

Crawling back into bed, Teddy mumbles incoherently and snuggles up to my back. I didn't put any clothes on, and he is still naked from the night before, so we have skin contact all the way down to our feet. I'm taller, but Teddy's thicker arms wrap around me in a way I've never experienced before.

Normally, I'm the one taking care of him, but I like this version of Teddy. He is all type-A, take-charge with school, and there seems to be some of that when we fool around. The way he held my head in place to fuck my mouth the day before flashes through my mind and I cant my hips back into him.

"Mmph," Teddy grunts in his sleep and holds me closer, his dick sliding in the crease of my ass as he thrusts once.

Reaching back to grab his hand from my chest, I pull it down to cup my hard-on. Teddy gasps and I know he's awake now. He doesn't move, and I sober when I think about Teddy turning me down, but I will respect whatever he says he wants or doesn't want.

Instead of rolling away or pretending to be asleep, Teddy closes his hand around my length and strokes me. He twists his wrist at the end, and I can't decide if I want to thrust back onto his dick or into his hand more.

"Fuck," I follow his movement, trying to get more friction and he stills.

"Do you want me to jack you off again?" Teddy's breath is warm on my neck.

"No," Teddy stills his hand and I hurry to correct my meaning. "I want you inside of me."

Teddy still doesn't move, but I don't want to spook him. I'll let him process without my influence. After a minute or two that feels like an eternity, Teddy moves his hand to grab onto my hip again. His thumb moves lazily along my crack like he"s thinking about my words.

"You want me here, Jamie?"

"Yes," I push back so his dick drops to my hole. Teddy seems to feel the lube there as his head catches my rim and he grips my hip hard enough to leave bruises. "Please, Teddy? I want to try."

"Condom?" Teddy manages to grunt out, and I reach for the nightstand. I tear the packet open and hold it over my shoulder. He takes it and I hear him huff in amusement at my preparedness, which cuts off as his dick meets the back of my balls and we both gasp at the sensation. "You want it like this?"

Facing him feels too intimate for the first time. I'm worried he'll panic and call it off if we're eye to eye, facing what this means for us. Hell, I might spook with that level of intimacy. Besides, the first time? That implies there will be more, and I don't know if there will be.

"Yeah, just like this," I turn my head to kiss him and he melts into me.

We kiss sloppily at the odd angle as he slips the condom on. I break the kiss to get the lube, pouring some out and reaching for his sheathed dick. Teddy shudders as I coat him and guide him to my hole.

"This won't hurt you?" Teddy asks when he's lined up at my entrance.

"I prepared in the shower before you woke up, but it might hurt a little from what we read. Just go slow."

Teddy nods against my shoulder and the head of his dick nudges at me. I let go of the breath I'm holding and he slips past the tight ring of muscles I loosened with my fingers. There's a slight sting and he stills when I make a whimpering sound.

"You good?"

"I'm alright, keep going," I reach back to hold his hip and encourage him to push on. Teddy thrusts in short bursts, getting a little deeper each time until he hits the spot inside me that had me seeing stars when I got off the day before. "Yes, right there."

"Fuck, you really do have a tight ass," Teddy pulls almost all the way out and thrust back in to hit my prostate in one go, and my dick that had flagged rallies back to life.

"Jack me off, Teddy," I tell him as he picks up the pace on my ass.

My whole body feels like it's on fire in the best way, molten lava that consumes everything around us. His grunts and my moans have driven out the sounds of the storm. I can feel nothing but his hands on me as he uses the arm around my neck to reach for my nipple. One hand on my dick and the other twisting my peaked flesh, I'm on a hair trigger.

"Oh, go–that feels so good. I'm not going to last."

"Me either," Teddy pants, his hips meeting my ass and echoing through the room as he picks up speed. "I've never felt anything as good as you."

Teddy hits my prostate just right and I go off like a rocket, my cum spurting out on the sheets. My ass tightens around him and he stutters, thrusting one more time before a full-body shiver racks him as he goes still.

"Jamie," Teddy calls my name as he comes and my dick lets out one last burst after feeling his dick throb inside of me.

I've never felt anything like Teddy inside of me, and I don't think I can have this be the only time.