They retired from the life without a shred of guilt, set up a nice little house on ten acres, with a huge organic garden for Sam, where he grew every kind of fruit, vegetable, nut and legume the climate would allow, extended with the greenhouse Dean had built for Sam's 35th birthday. He even made wine during some years, purple-black Syrah which he bottled with a hand-operated corker, emblazoned with a simple black wine label with the anti-possession symbol in black, and the words Winchester Winery.
There was a repair shop for Dean, complete with a machining section where he got to show everyone what a genius he really was, engineering and fabricating complex and beautiful parts. Sam wrote books now, meticulously researched tomes that were considered the new gold standard for supernatural lore.
They had the best mattress money could buy, a nice wide California King to accommodate them and their two dogs, a custom bed frame and headboard that never so much as squeaked, with concealed O-rings and places for hooking restraints that could take the full force of Sam or Dean tugging with all his strength. They had central air and heat, a fireplace in the living room and the bedroom, a full larder, a wine cellar, and a commercial Wolf gas range. On the master bedroom's deck was a beautiful redwood hot tub, large enough for both of them to stretch out, where they could soak with a drink in their hand, dogs napping on the dog beds set out on the redwood planks, surveying their property as dusk turned to real country dark and the fireflies came out to dance.
They had everything they could ever want. Keys to the castle.
But every now and again, they both got that itch. They called a trusted friend to come dogsit and guard the property, and they hopped in the Impala for a road trip. Canned soda and beer nuts as they drove, cold beer and hamburgers at a diner, wet sloppy side-of-the-road blow jobs. And the real destination. The motel. With its stiff plastic keycard. Shots of whiskey straight from the bottle and sweetfilthy motel sex on the stiff sheets. And rough carpet. And in the shower, faucet sputtering under the weak, erratic water pressure. Falling asleep in each other's arms, bare skin daubed blue and red from the neon lights shining through the thin polyester curtains.
They always came back so happy and relaxed, their friend assumed they had stayed at a nice B&B or done one of those ranch work vacations.
Sam and Dean never mentioned they'd never gone farther than 100 miles from home.