Anne's Trunk Pt. 01

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Pleasure blooms in the Highlands.
2.6k words
4.25
14.1k
4

Part 1 of the 2 part series

Updated 06/09/2023
Created 10/24/2019
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ValoryG
ValoryG
287 Followers

Note: Names used here are entirely fictional. Any resemblance to living or deceased persons is entirely unintended and coincidental. Some of the place names are fictional.

***

Along the coast of Scotland's far northern reaches, the Highlands meet the North Sea along a series of spectacular cliffs. Despite their beauty, they don't command much tourist attention. This area of Scotland is also one of its poorer areas, where families generally make their living with fishing, raising sheep, limited agriculture, and servicing and manning the natural gas and oil rigs off the coast.

Back in 1941, during World War II, the area was busier. Because England maintained its major naval bases in the islands just to the north, the area had come under German naval and air attacks. Flying from their bases in Norway, Germans had even bombed and strafed small towns on the mainland with no military facilities.

One of these towns was Cleugh, with a population of only 250, along Highway A9, about 60 miles south of the naval bases. Although Cleugh itself hadn't been attacked, the next two towns to the north had. The populace was justifiably apprehensive and tried to prepare for the worst.

The only things Cleugh were known for were its Hempstead Inn, an oasis of food and lodging for upper-scale clientele and visiting military officers, and an ancient church with its graveyard.

Gerald MacFinnis, 34, lived in a farmhouse a few miles out of town with his mother, invalid sister and two nephews sent up from London to escape the German bombing. Because Gerald's father had died young, the remaining family members all needed his financial support, so he hadn't been conscripted into the military. This embarrassed Gerald as he watched more and more of his schoolmates joining the military, and even hearing of the death of several of them.

Rather than becoming involved with his family's sheepherding, Gerald had gone to trade school to become a mechanic. And a good one he had become, owning his own shop in Cleugh along with an older mechanic. Due to the proximity of visitors to the Inn, he had developed a deserved reputation for working on foreign cars, and his ability to keep cars in service despite the lack of replacement parts was well known.

You might ask how these well-heeled, foreign-car owners were able to keep driving their cars during the war, with rationing of gasoline and oil. Well, even in wartime, money speaks, and gasoline could be purchased on the black market. Gerald wasn't about to ask about these things.

Only six months after the outbreak of war, the local constabulary had begun the work of setting up a volunteer Home Guard to watch over the miles of rugged coastline should the Nazis try to send in spies or demolition squads by boat or parachute. Gerald finally saw his chance to assuage his guilt by joining. Most of the other volunteers were older than him - say, older than 40 - too old to have been conscripted.

In some areas of Scotland's coast, all the volunteers had to do was sit in observation points with binoculars and telephones. But in the Cleugh area, the coastline was so rugged, with so many ravines and coastal indentations, more was asked of the men. They had to trudge along old trails atop the bluffs, and they had to carry radios with them. So it was that Gerald, a stocky young man in good shape, pulled duty two consecutive days per week. He was issued, and dutifully wore, a dreary uniform consisting of a long brown overcoat (to stave off the cool-to-cold winds), tall boots that required a good deal of lacing, a classic English helmet, a bag containing a rain poncho, and an English World War I-vintage rifle with a bayonet. For the rifle, he was issued a grand total of 10 bullets and was given one day of target and bayonet practice.

The radio, in order to conserve weight, could only transmit, and only in Morse Code at that.

At first, having to hike 12 miles per day - six miles to the turnaround point - and back - tired him out, but he quickly adapted and sometimes even enjoyed the bracing cool air, the sea birds, and the vistas. However, rainy days could be a slog.

Sometimes while on duty he met the other volunteers to the south and north of his sector. He already knew Brian, to the south, a gent of about 50 years of age, who smoked a pipe, and seemed far more convinced that the Germans would invade their town than Gerald did.

There was one unique thing about Gerald's route that he was barely aware of prior to his enlistment. About midway in his sector only a hundred feet off the trail was a small, sturdy home that had been built of stone several hundred years before, with a marvelous view of the sea. Oftentimes, such homes had been neglected and fell to ruin, with roofs caved in. But, he was told, this home had been rescued by a retired doctor named Anne in her sixties who was somehow connected to the owners of the town's inn. Of two stories, the home was in nearly perfect condition, with beautiful windows, two fireplaces, but only about 45 feet long.

Gerald was told that when war broke out and the naval base to the north had been attacked, Anne became so fearful of her isolation and vulnerability that she went to live with a sister in Ireland. She handed over her key to the local constable, and asked him to keep an eye on things. Fortunately for Gerald, it was decided that the Home Guard on his sector would be provided the key should they need a shelter when caught in a storm.

One day, a month into his new duty, Gerald was faced with a rainy, cold day and a lashing wind, so he let himself into the solid, cozy-looking home. Setting his bulky radio down on a table, and determining that the electric lights worked, he surveyed the interior. It was much, much neater than his own home, and, he surmised, typical for a professional woman living alone. There were neatly hung pans above a newish stove, and comfortable stuffed chairs in a living room with embroidered white doilies. On shelves were vases with carefully arranged and dried flowers-on-stems that she'd apparently picked, and family photos adorned the walls. There were two bedrooms upstairs, with the beds neatly made, topped with feminine pillows. In one bedroom, there were more photos, set atop a large wooden trunk of approximately three by six feet. These were mostly group photos of, he guessed, groups she'd been associated with at a university.

He was tempted to look for food, but decided not to abuse his privileges. So he spent the rest of the day periodically looking out the windows for Germans, reading a novel from the woman's extensive library, and letting his boots dry out. When the weather eased, he headed back outside to his starting point.

At the end of his two-day shift, he handed over the key to the next warmly clad Home Guard volunteer. This key exchange went on, week after week. He never asked the other guards if they used the place. Something in him wanted to think that it was his to enjoy, alone.

He began to stop at the house more than he needed to. It was an oasis of peace and quiet that relaxed him after the hubbub of his home and business. As for Anne, he was sure he'd never met her, and was quite curious about her and how the well-off lived. He had been told that she had practiced medicine in the Glasgow area.

He soon identified her in the photos. A little haggard and dowdy in her old age, she in her younger years was quite pretty, with dark hair and and an attractive figure, and always with a smile. But there were no photos of her one-on-one with a man or with children. There were also some photos of her in foreign locales.

Her bookshelf held mostly classic and popular novels, plus travel books. There was a record player with mostly jazz and classical records. Imagine, jazz in Cleugh!

As Gerald kept familiarizing himself with the place, he was worried that someone would spot him enjoying himself too much. So one day with his car, he located the driveway to the place, and was pleased to be stopped by a locked gate.

Anne had apparently left with all her clothes, because the closets and chest of drawers were bare. But one thing mystified him: the large trunk next to the bed in the bedroom she had apparently used. He was drawn to see what was inside, but it was locked with a simple built-in lock. Being the mechanic he was, such a simple impediment didn't stop him for long.

He made a drawing showing where each photo was on top the trunk, and then removed them. Finally, he pulled open the top, and he was surprised when one of the hinges pulled off the body of the trunk, so he had to be very careful the second hinge didn't follow suit.

The pleasant smell of cedar reached him. Inside, laid out quite deliberately and carefully, were various items of clothing along with some jewelry in wooden cases, and some mementos from foreign trips. So, this is how a woman with money dressed! His own mother had always dressed plainly, even when she traveled. Her clothing was of very muted colors, or simply black and gray.

Next he compared Anne's clothing to that of his long-time girlfriend Jane, who worked the front desk at the inn, and did his bookkeeping. Jane was more fashionable than Gerald's mom, but she obviously couldn't afford some of the expensive clothing Anne had packed away.

Gerald felt rather sinfully excited, as though he was slowly undressing a woman, when he began to examine Anne's things. At the very top of the trunk were several tailored and quite soft wool dresses along with some floral-decorated scarves and a box of simple earrings and necklaces. There were also several cotton dresses. All this was quite conservative as befits a retired doctor in her sixties. Just to the side of all this were two shoe boxes with seemingly expensive, but still simple Italian shoes.

Something made him want to look just below the surface, so he made mental notes of where everything was that he carefully pushed aside. He was half amused that he was like some archeologists who had done a dig just outside town before the war, carefully working their way down through layers of artifacts from an ancient fishing village.

Gerald was surprised and pleased to find what he would call a full-body girdle, with a zipper down the side, and an open bottom with garters. He had never seen such lingerie as this - so, he thought, that's how some older women were able to display smooth curves!

Just touching the sparkling white girdle was rather magical and exciting - definitely a forbidden activity! The sexy way the item was constructed - of elastic and satin in strategic places, with artfully placed embroidery and seams - and the way the cups felt to his exploring fingers - all seemed cunningly designed to turn him on. For a moment, he imagined being a peeping tom and watching through her window as Anne pulled on the girdle and zipped it up, and adjusted her breasts inside the cups. The cups would jut out nicely. With that thought, he felt an erection forming, and he suddenly felt so guilty and perverted that he put everything back in place, including all the photos, and resumed his patrol duty. But even then and back in Cleugh, he found it often hard to stop thinking about the treasure trove of Anne's clothing, and wondering when he could return.

When he was working on cars in his shop, playing the experienced, capable and virile mechanic, he sometimes wondered what else was in the trunk. And when he was with Jane and kissed her goodnight, for a weird moment, he replaced her in his mind with Anne. When he moved about Cleugh, or dealt with female customers, he began to wonder what sort of lingerie was hidden underneath their dresses or skirts. When he saw the subtle hints of bras or girdles or straps underneath dresses, he would have involuntary erections which he took pains to hide.

During his next visit to Anne's cottage, two weeks later (Gerald thought it wouldn't look good to use the place every week), after a look out the windows to make sure no one was in the vicinity, he wasted no time removing his coat and heading upstairs. The trunk beckoned him, and the top was quickly opened. He admired the long girdle once again, but this time delved deeper, putting items aside on the floor. But he stopped short, realizing he'd never be able to recall exactly where everything belonged, and he didn't want Anne returning and accusing the Home Guard of messing with her clothing and intimates.

So he resorted to digging down along the corners or sides of the trunk, and if he felt or saw something of interest, he'd extract it, marking the place with a magazine. So, on this visit he found several slips, with lovely lace at the top, one of an off-white color and the other plain white. More of interest were four panties, two plain cotton and two of nylon edged with some lace, of the same white and off-white colors.

He found himself smelling each of these items, and was rewarded with a faint perfume which Anne must've favored. There were more dresses (this time of a silky rayon), a few packages of unopened nylons, and finally, two bras. These were a little like those Jane wore, but of a ritzier, shiny fabric and nicer detailing. Just running his fingers along the slick material of the cups and the elastic of the back straps gave him an urgent erection. His senses had reached a heightened state, and he felt rather intoxicated, like he was off in another world.

In a way, he felt he was betraying Jane by becoming involved with the vestiges of an absent woman. And, he felt again, he was bordering on perverseness. But the richness of the experience overwhelmed him, and he followed his strong inclination to take off his trousers and insert his penis into a cup of the sexiest bra. When the two touched, he stiffened with pleasure and closed his eyes with utter enjoyment. When he looked again, his wetness had left a moist area in the cup. He excitedly began to pull the cup against his cock again and again until he exploded with cum.

He returned to earth after a long swoon.

And now, what would Anne think of a bra all stained with dry cum? He realized that he would have to secret this lingerie away somewhere. And so he hid it away out of sight inside Anne's chest of drawers.

In the future he would need to be more careful!

And, he worried, would he become more attracted to his girlfriend Jane's lingerie than to her? Would she figure out what he was up to?

Was he abandoning his duty to watch for Germans? Violating his oath to be always vigilant? He could see the headline in the local newspaper: HOME GUARD VOLUNTEER MISSED GERMANS WHILE MASTURBATING INTO BRASSIERE.

(Part two coming soon. This is a story I'd wanted to do for months and am glad to see it shaping up ... )

ValoryG
ValoryG
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AnonymousAnonymousover 4 years ago
Confused

How is this transgender or crossdressing? Hopefully you will either fix it or change category

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