Anne's Trunk Pt. 02

Because of his guilt about his messing with Anne's bra, he avoided her house, thinking that either someone would learn about his indiscretion, or that his girlfriend Jane would notice something different about him.

But over the ensuing weeks, he came up with all sorts of rationalizations as to why he could continue to explore her box of earthly delights. Such as, after all his volunteer patrolling and dedication, he deserved a reward. Or, his growing excitement about feminine lingerie could raise his libido and make his sex with Jane better. Or, you only live once, so why disregard something so exciting?

Nonetheless, he had to wait until the next winter storm came in. Finally, when one was predicted to last three days, he informed his Home Guard coordinator, his family and Jane that he expected to overnight at Anne's.

So, after completing his patrol duty on the first day, with the rain and wind behaving nastily, he let himself into Anne's with heart beating fast, and locked the door. Now, like putting off dessert until an hour after dinner, he carefully lit a fire in the fireplace, shut curtains, had the dinner and a beer his mother had provided, and took a shower in Anne's quite-small bathroom.

By this time, the fire was heating up the small house nicely, which was such a comfort considering the cold wind and rain whipping around in the dark, outside.

He toweled himself dry, wrapped the towel around himself like a skirt, and made his way upstairs. There was that beckoning trunk again, with the photos on top. It was like the presence of Anne in the photos was looking over her clothing, both admonishing Gerald not to touch, and at the same time, seducing him with all the possibilities.

Off came the photos. As he carefully raised the lid, he felt his penis also rising.

He removed the long girdle, let his towel slide off him, and brought the girdle in contact with his dick, which promptly pointed even higher. But rather than do a repeat of what he did with the bra, he had the discipline to put the garment aside. He was more interested in digging deeper into the trunk, hoping to find some even more exotic and sexy things.

When he got down to the previous level he'd reached, about halfway down, he extracted the sexiest pair of panties, the remaining bra, and a very feminine dress, and slipped into them clumsily -- especially the bra, because it was too small to secure the hooks in back. He had to rummage through the house for some rubber bands to make the back band long enough. He stuffed the cups with tissue paper, and absolutely admired the shapes of his new breasts. Gerald enjoyed every moment of feeling the silky and feminine fabrics against his skin.

Zipping up the dress, too, was an effort. But finally, there he was, feeling quite womanly, with a very firm erection.

So clothed, he now dug further into Anne's past, because it seemed that the deeper he went, the younger the woman he encountered. Now, within a foot of the bottom, Gerald began finding more adventurous and sexy things.

Gerald quickly calculated: if Anne were 60 now, what he was encountering might well be from the roaring twenties, when she would've been in her late 30s. And virtually everyone knew, during the 1920s, in the excitement following World War I, many women had felt emancipated and independent and looked for a good time. He suspected that Anne was from a moneyed family, and would have been likely to enjoy life to the max. Unlike Gerald's mom!

Gerald excitedly found a sheer black bra with a few pearls sewn in, a red satin bra with little bows, and a brown lace bra that extended downward toward one's navel. Even its straps were made from lace.

Panties were numerous, and offered the same variety. Some were silky and loose, like shorts, while others, always of a shiny fabric, were quite brief and close-fitting. Some were plain, while others were very sexy and elaborate, with lace or embroidery. While handling them, he put his hand every so often over the panties he was wearing, to push them against his dick. Surely he thought, he had entered heaven, and the only thing he lacked was real women to model the lingerie for his benefit.

Then there were the dresses. The ones she'd saved reminded him of pictures he'd seen of the flapper era when women favored the boyish look, with sensuous silk-like dresses hanging loose, without showing much bosom or waist, and with nice ornamentation. Why, no one would wear these today! But back in the day, he surmised, Anne must've really led a racy life -- at odds with the photos of her dressed conservatively with her classmates on top the trunk.

Very near the bottom of the trunk, he found another elasticized girdle, for the hips alone, of a light blue color. And, surprisingly, protected in a silken pouch, was a short wig! And some black-seamed nylons.

At the very bottom, was a very old-fashioned-looking -- almost industrial-looking -- corset with stays and boning, and a laced-up portion. Evidently meant to cover the body from thighs to waist, it seemed incredibly complicated and yet rather exciting. Perhaps Anne had worn it before being liberated from such things!

When he looked at his wristwatch, it was already midnight. Where had all the time gone, he wondered. Just as he had penetrated all of Anne's layers, he carefully returned all the items to their proper locations, with one exception: he had also come across a diaphanous sleeping pajama with very delicate floral designs, with a loose top and only a very few frills about the neck, and loose pants with a drawstring. Gerald replaced the clothing he was wearing with this, and in a dreamy state took to Anne's bed, imagining he was a girlfriend getting into bed with a young Anne. And Anne would be wearing the exact same pajamas.

With the electric lights turned off, and the storm howling outside, and the rain pelting the windows with a vengeance, he felt wonderfully secure and whole, a feeling that had evaded him for most of his life. He felt relaxed, happy and fulfilled.

Later that night, he dreamed that he met the young Anne and she invited him to join her in a cab, where they were on their way to a party. On the way there, she insisted on putting lipstick on him, saying that all the men did that. She wore a dark dress with portions that were enticingly transparent, and seemed a little preoccupied and distracted. When Gerald asked her about her college days, she replied something like, "That'll have to wait; there's too much fun to be had, don't you think?"

He awoke to daylight and the storm still raging outside, went downstairs to fry some eggs for breakfast, and hungrily consumed them alongside bread and jam. All the walking-patrolling had given him a good appetite.

After a cursory look outside to confirm that the German army hadn't landed and their battleships weren't in view, he hustled back upstairs.

This time, he could no longer resist the urge to try on the long girdle he'd first found in the trunk. Pulling it on was a major struggle, but after much effort, it was in place, with its straps tight over his shoulders. The controlling garment pulled in his waist and projected sexy cupped breasts. He was heady with erotic excitement.

Throwing all caution to the winds, he found and opened one of the packages of nylons in the trunk, and managed to pull them up his legs, with only one run. Then he had to figure out how to attach them to the girdle's garters. So much to learn! But every step along the way brought him to a new plateau of pleasure.

Finally, he put on the dress he'd worn the previous evening, and to top it all off, he reached deep to retrieve the wig, and fitted it to his head. It was a short style, of a dark brown color. He was also able to locate a small makeup kit kept near the top of the trunk, found lipstick and tentatively applied it. He was so thoroughly amazed that women had such exciting things to enhance themselves with; he'd paid so little attention to these things before.

Because his dick was peering out from underneath the girdle, it was contacting the dress and leaving a wet spot. So he pulled on a pair of panties to cover it, and went to admire himself further in the mirror once more. From garage mechanic to woman! He reached up to feel the cups of the girdle under his dress, imagining he had breasts, and ran his hands over his now-smooth buttocks and around his narrowed waist. At that moment in time, he wished he'd been born a woman; had been able to lead a life like Anne -- certainly not a life like his hardscrabble mother's. Or even a life like his girlfriend, who was pretty and had a nice figure.

After so much rapture imagining being a woman, his sexual energy was quite pent up, and it wasn't long before he was lying on Anne's bed, hiking his dress up, and pulling his panties off. Looking at the rise of his breasts under the dress and thoroughly enjoying the tightness of the long girdle, it took only a minute or two of hand play to explosively climax and spurt. He lay there in the pool of his pleasure for a good long time until the sounds of the storm re-entered his consciousness.

He put all the clothing back, semen stains or not.

Good god, he was going to have to walk miles back to his car in the rain! But that he did, and returned home to a good meal amidst family members. His mom asked him how the overnight went, and Gerald replied, "Oh, it's a pleasant house, but there's not much to do there other than listen to the woman's radio."

Gerald's next chance at womanhood, or the semblance of it, happened a month later. The weather had begun to turn a little warmer, and the storms that came in weren't as strong, but he again received permission to overnight during a period of rain.

As he walked his patrol the first day, there was alternating sun and rain, with rainbows out over the sea. He saw several British military planes flying along the coast, and a fishing trawler out at sea. He still hadn't had to use his radio to report anything unusual, other than checking in at the beginning of his stint, and, to tell the truth, he figured there'd be never be any wartime excitement on his watch.

As the day headed toward darkness, he arrived back at Anne's, quite hungry -- for both food and for opening his treasure box. That evening, in the privacy of the upstairs, he dressed up again, trying on a different dress after pulling on the long girdle. There was something about its tightness and authority that he liked. This time, in addition to the wig and lipstick and all, he added a necklace, bracelet and shoes (which barely fit). He thoroughly imagined himself to be a woman, a young Anne. Sitting down in a comfortable chair, he read a book until he was so tired he had to retire.

Once in bed, he masturbated once more, while wearing the very feminine pajamas. And then fell heavily asleep.

Sometime during the night, Gerald awoke to something other than rain and wind. No, he must be dreaming, he thought. But there it was, again. It seemed someone was banging on the door and yelling to be let in. Impossible! He wanted to pretend he wasn't there and let them give up and leave. But that wasn't to be -- the person or persons kept pounding. Maybe it was because he had left a feeble light on downstairs, so they assumed someone was home!

Grumbling, he deftly slipped out of Anne's pajamas and put on his uniform trousers and shirt, and made his way downstairs. He peered out the window and saw a figure outside and went to open the door. The person was gasping from all the shouting, and looked to be soaked from the rain, like a wet seabird.

"Come in, please," said Gerald.

"Thank you," said the figure. A woman's voice. Now he could make out a woman's face, too, and matted long hair aside that face. "Do you suppose I could dry out here?"

"Yes, of course," said Gerald. "But what are you doing way out here in a storm in the middle of the night?"

"Oh, my apologies. But I was out here birdwatching today, and lost the trail, and couldn't get back to my car before it got dark. I was afraid I'd have to spend the night under a tree, but it eventually dropped water on me too, and I got so wet."

She lay her knapsack on a chair, took off her poncho and without asking permission draped it across another chair. She wearily sat down.

Gerald proceeded to get the fireplace restarted and soon a warmth began to fill the room. She said she could use a bite to eat, so Gerald located a package of instant oriental noodles and began boiling water.

"What's your name; where are you from?"

"Kirsten. I'm from Edinburgh. Staying at the Inn."

"You grew up in Edinburgh?"

"Oh, yes."

Something began to make Gerald more alert. Now that he was fully awake, his mental faculties had sharpened, and there was something about Kirsten that bothered him. It was mainly her accent -- it wasn't a south Scotland accent, and it wasn't the accent of a woman from a big city.

As she sat there eating her noodles, he looked at her closely. Definitely a European face.

"So, what do you do out here?" she asked, perhaps wishing to deflect the attention she was getting.

"This isn't my home," he offered. "I'm in the Home Guard, and I'm out here two days every week on patrol. I walk the cliffs trail. When it gets stormy, they let me overnight here."

"So," she asked, "on other days there are others out here on duty too? Do they stay here too?"

"They could, but I'm not aware that others have used the house."

Changing the subject, Gerald asked, "What time did you arrive at the Inn?"

"About noon yesterday; why do you ask?"

"Because that's the shift my friend Donald works at the front desk there. Did you meet him?"

"Yes, I think so. A very helpful gentleman. He told me to try the trail here for birdwatching."

There was only one thing wrong with the answer: Gerald's girlfriend would've been working there at that time. In fact, no men at all worked the front desk.

Gerald looked at the knapsack. It didn't look Scottish, or English for that matter. There was no brand logo on it, but it looked more like it came from the Continent: France, the low countries, or ... Germany.

Gerald excused himself to go into the living room, retrieved his rifle and tried to be very silent as he placed a round in the firing chamber. Just as he was turning around to confront Kirsten on his possibly faulty suspicions, there she was in front of him, smiling, pointing a German Ruger pistol at him.

Now her English was heavily tinged with a German accent. "So, Gerald, you are too smart for your own good, aren't you?"

"And your real name is ....?"

"Jette."

"And now, I must figure out what to do with you. Kill you? Make you step off the cliff into the sea? You disappear, and the Home Guard might think you were a hero, eh?"

Gerald didn't say anything.

"But while you were checking me out, so to speak, I was checking you out. You might explain to me why you have traces of lipstick around your mouth, and why there are some strands of foreign hair in your own hair -- like maybe you had worn a wig. I know that English barristers wear wigs, but not lipstick!"

"This is none of your business, whatever your business here is."

"Do you like to dress up, my freulein?"

Gerald was silent.

With her Ruger, Jette motioned for him to go upstairs, and Gerald had no choice but to comply. He went into the guest bedroom, which was in pristine condition, but Jette quickly saw that he'd been sleeping in the other bedroom, so that's where she directed him.

When he'd returned things to the trunk the night before, he hadn't quite gotten a silken panty entirely under the cover; it was half hanging loose outside. But that paled in comparison to Anne's soft and filmy pajamas, laying on top the bed.

"Sit down, my freulein," she ordered, and she fingered the delicate pants and top. "Very nice, sir. Wearing these helps you get to sleep, or perhaps they excite you?"

Next she walked over to open the top of the trunk. "Oooh, la, la," she exclaimed as she held up the wayward panty. Next she held up the long girdle. "I can see you wore this, Scotsman. ..... I'll bet you enjoy wearing it under your kilt, don't you?" With that, she laughed shrilly.

Gerald wasn't enjoying the humiliation. But on the other hand, in a perverse way, sharing his fetish with a woman, even if a German woman, was a little thrilling.

"Tell you what," said Jette, "I'll let you live a while longer if you do me a favor. You must dress up for me. It will be fun to help pass the time until I leave."

"I never dressed as a woman until I came here. I succumbed to the temptation."

"How interesting and quaint! So, I will tell you exactly what to wear. First, the panties, followed by the girdle, or the corselette -- whatever you call it in English. But before you do that, remove the boot laces from your boots and leave them on the floor."

Gerald did as instructed. He noted that Jette was enjoying herself immensely. After removing her coat, her breasts pushed healthily against her brown sweater. And after she had absorbing some heat from the house, color had come to her cheeks, and her hair looked better.

Standing there, he waited as Jette selected a dress and threw it over to him. She also located his wig and nylons and then waited for him to put all of these things on. He felt even more clumsy than when he dressed by himself, and must've blushed a hundred shades of red, having to exhibit this private part of himself.

Jette noticed.

When he was finished, feeling more like a wounded Scotsman than a woman, she told him to sit in a straight-backed chair and put his arms behind him. She picked up a boot lace and went behind him, to securely tie his wrists to the back of the chair. Next, also from behind, she tied his ankles to the legs of the chair.

"Oh, mein gott, we forgot your lipstick," she exclaimed. "Where would I find it?"

He couldn't believe he was playing along by disclosing its location. She came over to carefully apply it to his lips while sitting in his lap. She applied some to her own lips, then pushed her lips smack against his. He'd tried to move his head aside, but she'd held his chin tightly.

"Oh, look at you," she laughed. "You have bruste -- breasts -- and women's hair and lipstick. What more could a girl want?"

She slipped off Gerald's lap and reached under his dress to find his bulging dick inside his panties. "Oh, dear," she said, "your puppy dog wants some attention!"

Gerald looked aside.

"Do you have a girlfriend?" she asked. "Do you like to wear her underwear? Does she know about your fetish, eh?"

He didn't answer, but struggled against his bonds. The more he struggled the more the thin leather boot laces cut into his skin.

Jette left the room briefly, and Gerald was unable to remove himself from her expert ties. When she returned, it was with a little packet, which turned out to be a military-issue condom. She hiked up his dress, pulled his panties down and rolled the prophylactic expertly down his erect cock.

"Going to get a free fuck from the enemy?" he asked.

"Oh, this thing about war, I just see it as a big game," she replied, as she disrobed. "You know, it's just like chess. We're probably going to lose the war, but I like the thrills and danger, you know, especially as a woman."

Jette was down to her panty and bra, and it was a sexy, black bra. As her panty came off, her German cunt came into view. She had quite a lot of pubic hair, and her body was in finely toned shape, as befit a military person. Jette came over to sit on Gerald's lap again, impaling herself on his ready-and-waiting prong, putting her arms around his neck, and beginning to kiss his neck and ears.

"God, how did I ever get to this place?" he asked himself silently.