Now the building is a couple of hundred years old, but ghosts can't be blamed for the runaway rubbers, which in Chris' mind only leaves one other plausible answer: they're probably being pocketed by the local teenagers.
And that's his dilemma - should he put the condoms behind the counter where they can't be stolen, or should he leave them where they can be easily snatched, for the good of the local community?
As with every business decision that Chris has made in the 18 months he's been managing Blockley's busy village co-operative, he's opted to do what is best for the local people, which in this instance means helping to keep the teenage pregnancy rate nice and low.
The Blockley Village Shop is the heart of the community, supplying its residents with quality local products and well-known convenience food brands, while keeping its spirit alive with vital services and local events.
But this hasn't always been the case. Rewind two years and the picture postcard village of Blockley didn't offer that much to write home about. Competition from neighbouring supermarkets, sky-high rents, a boom in online shopping and changing demographics had seen the once vibrant shopping street, which had boasted more than 30 shops and pubs, all but crumble.
By late 2007 many of Blockley's shops had been converted into homes, and the last remaining grocery store and post office was on its knees.
Something had to be done, and Chris, who at the time was running one of the village's cafés, was the man to do it.
With the help of 14 other concerned locals a sub-committee was mobilised, and after 18 months of meetings and minutes the Blockley village co-operative was born. "It was an exhausting but exhilarating time," remembers Chris. "All sorts of people from all walks of life offered to help us free of charge, from retail consultants to lawyers, and even the former Lovejoy actor Chris Jury, who helped publicise our cause."
Some 530 memberships were sold at £10 each, while generous donations and a £20,000 grant from the Village Retail Services Association (now known as Rural Community Shops) helped bring the fundraising total to more than £80,000. This was more than enough to lease a beautiful Grade II listed building in which to establish the community's new store.
And it was then that the really hard work began. The building, a former fire station, had to be carefully stripped down to make way for a good sized store, large adjoining café area and functional kitchen. Once again the local community pulled together. Shelving and fridges were supplied by the Mid Counties Co-operative, while local plumbers and builders sawed, wired, chopped and fired for free.
Finally, in April 2008, the jigsaw was complete and the village of Blockley was whole again.
"Business has boomed since day one," says Chris. "It's been frantic, but also fantastic."
After just nine months of trading the store had made almost £100,000 in profit - £77,000 of which went into paying the staff costs.
Unlike many other community run stores where staff often give their services voluntarily, workers at the Blockley Village Shop, including Chris, receive a wage, and a decent one at that. Chris himself works six days a week in the store and is helped by two assistant managers and 10 part-timers.
"The staff costs here are huge," says Chris, "but it's the staff who make this place so special."
And there really is a special aura about the store and its cosy café area, which on the day that Convenience Store visited was packed to the rafters with families and friends enjoying a warming cuppa and a catch-up.
"The coffee shop really helps to pull people in," says Chris.
Having run his own coffee shop, and previously worked in the hotel industry, Chris really knows his stuff when it comes to the food.
"The key is not to be too clever with the food," he says. "Simple but good-quality products such as bacon sandwiches and toasted paninis are what the customers want."
Chris believes that retailers don't have shell out a fortune in order to achieve a truly appetising offer. "I haven't got any big, fancy coffee equipment - a simple, but good-quality bean-to-cup machine does an excellent job," he says.
His crusade for simple honest food is also translated into the store area. "All of our vegetables, bread and the majority of our meat is locally grown and produced, which helps us to keep prices as low as possible," says Chris.
He also has a freezer exclusively supplied by a local farmer, as well as a chiller bursting with ready meals made by a resident from local meats and fish. Eggs, meanwhile, are delivered every couple of days from a nearby producer, and customers help keep her costs down by bringing back empty egg boxes.
Chris also has a comprehensive mix of premium and standard branded products on sale to meet the needs of Blockley's more discerning locals, as well as the hundreds of campers who descend on the area in the warmer months.
"We get quite a lot of trade from campers and people on weekend breaks who buy sack loads of convenience products. We call them the Pot Noodles," he adds. "They provide us with vital income so it's important that we cater for them, too."
However, it hasn't all been plain sailing for Chris and his crew. He's the first to admit that the slick retail operation greeting shoppers today took many months of tweaking and toning to get it into shape.
"I knew all about the food and drink side of things from my past, but I hadn't anticipated how difficult the day to day running of a store would be," he says.
Space is at an absolute premium in the miniscule stockroom, which was made even smaller in order to accommodate a sub postmaster's cubbyhole. "At first I found the ordering of stock really difficult; it was so hard to know how much to get of each product and where to put it all when it arrived!" he says. "I couldn't get over the volume of chocolate bars that we had out on display when we first opened and I was sure we'd made a mistake, but they all sell."
Blockley Village Shop & Café
In-store services: post office, licensed café, deliveries, local produce, large stationery section
Staff: three full-time, 10 part-time
Opening hours: Monday-Saturday 8.30am-6pm, Sundays 9am-1pm
The store has also experienced a few glitches with the post office counter, which is open 15 hours a week. Telecommunications problems have meant that essential services are often on the blink. Fortunately, Blockley's residents are very forgiving.
And they have good reason to be. In February an unexpected snowstorm all but blotted Blockley off the map, and the store and café was the only place for locals to get their food and drink, as well as essential news.
"We woke to more than 10 inches of snow," says Chris. "The village was marooned, and getting in and out was not an option."
However, thanks to Chris and the help of a loyal local with a powerful 4x4, the village was able to glean emergency bread and eggs to tide people over. "The snow highlighted the vital role that the shop plays in the community, not just as a place which provides essentials, but as a hub of information, support and laughter," adds Chris.
"A couple of years ago there was no reason for anybody to walk down the high street, but the store has changed all that. It's brought Blockley back to life."