Julia’s Femboy Son Returns Home

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Tem 16, 2022 // By:analsex // No Comment

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Jamie had never been the most masculine guy on the block. Or anywhere else, really. In his early teens, it had certainly been a sore spot. In those years, though, he managed to convince himself that he’d hit his growth spurt soon. However, the broad shoulders and muscular frame never came. Instead, he graduated high school with a build that could be charitably called “petite”. Except, ironically, for his wide hips. The pouty lips, soft skin, and silky, black hair didn’t help in that regard, either. The result of his woefully unmasculine adolescence was low self-esteem and a lack of sexual experience. Despite his academic excellence, not to mention the love and support of his mother Julia, Jamie could never quite ameliorate his self-image.

He held out hope, though, that things would be different in college. In a way, he was right. Just not in the way he expected. Soon after he got settled at school, he made friends. Faster than he’d expected, too. While most of these friends were girls, that wasn’t necessarily by design. As they got to know each other, however, he started to realize he just more comfortable around women. In a month, or two, his friends started to notice certain proclivities and, rather than ignore, or reject that, they encouraged it. Soon, Jamie was allowing them to dress him in their clothes on occasion. Not long after that, he was borrowing their clothes frequently, still not willing to pull the trigger on purchasing his own.

At the end of this first semester, Jamie found himself growing increasingly anxious about his return home. When his mother picked him up from the train station, he noticed that she’d cut her straight, chestnut hair to shoulder length for the first time in years. He noticed more about his mother now than he ever had when he was still chasing masculinity. He could now appreciate the way her brown eyes stood out against the slightly lighter shade of her skin. She kept her eyebrows neat, but just bushy enough to be noteworthy. Most of all, though, was the curvy figure his high school “friends” had never failed to comment on. The new light in which Jamie saw his mother was so distracting, he forgot to mention his gender identity until they got home.

While he hadn’t been particularly worried, it was still a relief when his mother was supportive of the change. He knew it was silly, but there had been some lingering thoughts of spending an entire summer at home alienated from his mom. Fortunately, that was not the case. Jamie had barely even needed to explain the change to his mom before she was planning a shopping trip to, as she put it, “Make up for two decades of cuteness.”

Frankly, she was a little too enthusiastic, but Jamie preferred that to the alternative. Her enthusiasm had to be put on hold, though. The first few days of his return home were actually fairly lonely as his mom had to focus on closing a sale. While he was a bit disappointed, Jamie could at least appreciate the passion Julia brought to a field he otherwise found dreadfully dull, realty. So, he passed the days mostly just reading and practicing his makeup.

In between rushing to and from the house she was attempting to sell, Julia still found a little time to show her son some affection. She made sure to compliment the few outfits he had that could be fashioned into a more girlish style, as well as offer suggestions where he could improve here and there.

Finally, on Friday, Jamie was lounging on the couch in the living room when his mother burst through the front door. Her hair crowded her face, hanging over her reddened cheeks.

“Sold!” She shouted in a voice was tinged with a manic glee.

As she strode through the living room and into the kitchen, Jamie admired the cherry-print, white sundress she had long-ago designated her “victory dress.” It wasn’t until his gender awakening that he noticed just how good she looked in it. Swishing on either side of that dress, though, were two over-full shopping bags and one slightly full takeout bag. Julia lugged them onto the kitchen counter with an exaggerated grunt.

Still reclining on the couch, Jamie called out, “Watcha got there?”

“Why thank you for your sincere congratulations, Jamie! I did work exceptionally hard to sell that house, you’re right! My victory dress, you say? Yes, it’s a bit worse for wear but I think it’s still quite nice. What an engaging dialogue!”

After a quick eye roll, Jamie hefted himself up and off the couch. He shuffled into the kitchen to give his mother a hug.

“Congratulations, dearest mother. Truly, you are a wizard of sales. Or houses.”

Julia cocked a skeptical eyebrow toward his belated theatrics, but appreciated the hug nonetheless. She squeezed her son, then gestured toward the bags on the counter.

“I thought a little celebration was in order, so I took a quick trip to that new mall that just opened up over where the YMCA used to be.”

Jamie glanced at the setting sun outside before he responded.

“Quick, huh? When exactly did you finalize adiosbet yeni giriş that sale? Wait– before that, did you say a new mall?”

Julia laughed at his incredulity.

“You’d think it was even more ridiculous if you knew how much that real estate cost. Nevertheless, I took the opportunity to do some celebratory shopping. When you see what I got, I don’t think you’ll have any objections.”

Jamie’s heart leapt a bit in his chest. His mother had mentioned a few times in passing that they should get him new clothes to match his new… him. The boy was as interested in the proposition as he was nervous. Despite the newfound comfort and confidence that he was enjoying day after day, part of him was still the slouched, short kid ghosting through the hallways of the local high school.

“First, though,” his mother’s voice interrupted his spiraling self-doubt. “We feast!”

And so they did. Julia and Jamie made light conversation about the sale, as well as the book Jamie had been devouring over the last few days while they ate the traditional celebration meal of the Martin household– pad see ew. When he was younger, Jamie had questioned the logic behind this choice, but nowadays he was content to just enjoy the Thai goodness.

It wasn’t until a couple hours later that they actually got around to the matter of the shopping bags. Up until that point, Julia needed a bath to recuperate from what, admittedly, sounded like an exhausting day.

When they reconvened on the couch, Julia slumped into the welcoming cushions with a sigh. She was wearing a soft, blue bathrobe that extended down to her mid thigh. She had brought the shopping bags that had Jamie so intrigued in one hand and a glass of wine in the other. Judging by the glint in her eye, Julia was well aware of that interest.

Julia twirled the glass and wiggled her eyebrows until Jamie got the hint. The boy’s fingers trembled slightly as he reached for the bags. He pulled the bag open a bit and peaked inside, as if that would make him less nervous.

Rolling her eyes, Julia kicked over the first bag, her bathrobe sliding dangerously up her thigh as she did. The wine had already put a glow into her cheeks, though the smirk was her own. The first item to spill out of the bag was a mauve crop top, while an off-white, midi skirt came tumbling after.

Jamie couldn’t help but grin as an image of himself in the outfit flashed through his mind. His mother watched silently as Jamie inspected the soft fabric of the top. The clear enthusiasm in his eyes was a joy to see. While Julia had accepted Jamie’s gender identity easily enough, she realized it hadn’t fully set in until this moment. She hoped her son didn’t notice she was tearing up.

After the initial impression, Jamie felt a bit silly to be reacting so strongly just to a couple pieces of clothing. He moved through the rest of the garments in the bag with a bit more haste, though still taking his time to appreciate the gift his mother was giving him. The crop top and skirt were quickly joined in a neat pile by a flared, navy dress, some frilly blouses, jean shorts, and a pair of skinny jeans.

At the same time, Julia had begun to pepper the event with some commentary.

She said about the dress, “I figured the shape would help a bit with your figure. Not that it really needs help. Those hips? That waist? It’s a wonder I never questioned your gender identity before, really.”

“You wanna talk about proportions?” Jamie shot back. He had heard from friends on more than one occasion that his mother was the star of a to-be-released Pixar film. It didn’t help that Julia found the comparison amusing. She had leaned into it a few times, resulting in weeks of ruthless teasing from Jamie’s friends. Now, though, he had to admire the woman’s figure, even if it was with a tinge of envy.

As Jamie reached for the second bag, excitement in full swing, a look of realization dawned on his mother’s face, one that quickly became concern.

Hesitantly, she said, “Maybe you should try on this stuff first? No sense getting spoiled for choice, right?” Even as she said it, Julia knew she’d fail to convince her son.

Jamie offered his mother one skeptical look before tearing into the second bag. At first, all seemed normal. From the top, he pulled out a streetwear-esque pair of overalls and some loose, high-waisted shorts. Then he saw it. Or them, rather.

Slowly, he turned to his mother, who had shifted from her sprawling, lounge posture to leaning forward with her head in her hands.


“I may have been a tad too excited.”

“Just maybe,” Jamie said, still in disbelief. The bottom half of the bag was comprised, primarily, of underwear. A thong here, some boyshorts there, and a few bralettes to round out the bunch.

As Jamie turned over an aggressively lacy thong, his mother squeaked, “I picked that one because– ahem, I thought it had some extra room down there.”

Jamie cast a side eye at the woman now staring adiosbet giriş at the ceiling. After a long moment, he cracked a smile.

“Well, I would have gotten here eventually, anyway. I guess I should thank you for the head start.”

Julia let out a deep sigh before she exclaimed, “Thanks, Jamie. Still embarrassed, though. I’m going to go get more wine. Why don’t you try something on?”

While his mother was presumably trying to drink away the mild shame, Jamie found that he was, indeed, spoiled for choice. The first such choice was what outfit he wanted to try on. The second, more drastic decision, was whether that outfit included his new underwear.

A few minutes later, Julia returned to the living room with a fresh glass of wine and a blush that would need longer still to fade. She found Jamie standing in front of the couch, wearing the first outfit he’d taken from the bags. The skirt went down to his knees, but the top only extended to an inch or two above his naval. Jamie turned and flashed her a grin. Julia fought back a fresh set of tears and, this time, blamed the wine for them.

“You look great!” She said. “Hot, even!”

Jamie giggled and covered his mouth, which further cemented his femininity in the moment. Julia looked at her son, impressed not only that he was really pulling the look off, but that she had picked out an outfit that suited him so well.

After a moment of admiring, though, Julia couldn’t suppress a nagging thought in the back of her mind.


“Guess,” Jamie said with a wicked grin.

Julia stared at her son, trying with the full might of her wine-addled brain to figure out if the boy was wearing panties. His poker face was infallible, though.

“I give.”

Jamie’s smile grew wider and, before either of them fully realized what was happening, flipped up his skirt. It was only for a moment, but Julia nonetheless got a clear view of a little bulge tucked neatly into a strawberry-patterned, cotton thong.

“Oh my God!” Julia turned away, laughing more from surprise than amusement.

“Hey, you bought them! I’m just showing my appreciation!”

Julia exclaimed, “But did you have to show me.”

Rubbing the back of his neck, Jamie replied, “Well, maybe not”

“Well,” Julia said after a gulp of wine, “snakes out of the bag, now. Let’s see the rest of the outfits, then!”

Near-high on newfound confidence, her son complied. He stripped off the crop top first, revealing to his mother a surprisingly taut tummy. His nipples were bigger than she would have expected, and their tawny color stood out from the light beige skin of his flat chest.

Off came the skirt, next. Julia tried to play it cool, but the sight was, well… hot. For a few moments, while he picked out the next outfit to try on, Jamie stood in the living room naked but for the little thong hugging his package. She did well not to stare, but the surreptitious looks over her wine glass weren’t the most subtle.

When Jamie finally turned around to step into the jean shorts he’d picked up, Julia could see she hadn’t exaggerated the boy’s proportions. His ass was remarkable in every way an ass can be. Round, supple, but tight. She had to dismiss the idea of a playful spank because she knew there wouldn’t be anything playful about her intentions, or the desires that informed them.

After the shorts went on, Jamie commenced with the impromptu fashion show. Everything she had felt about seeing him in the first outfit stayed true for the rest. Though she still liked that first outfit the most, the rest were all good in their own ways.

As the boy took off the last outfit, he paused for a moment to look over all his new clothes.

“I guess that just leaves these to try on next, huh?” Jamie gestured to the rest of the underwear still waiting in one of the bags.

“By all means,” Julia told him. She was determined to be the cooler one about this situation, even if the flush in her cheeks, or the tremor in her hands said otherwise.

When Jamie balked, his mother felt a mix of relief and disappointment.

“I’m not gonna just stand here alone in my undies.”

“Oh, so I should join you? Nobody wants to see that.”

“Psh, you know you’re hot. Modesty doesn’t suit you.”

“Besides,” Julia continued, ignoring his comment and the heat it put on the back of her neck, “I couldn’t join you even if I wanted to.”

Jamie gave her a quizzical look for a moment, but then figured it out.


With a coy smile, Julia assured him, “It’s a bathrobe, dear. What are we, Puritans?”

“Clearly not,” Jamie shot back, shooting a glance at the bag still half full. Once his eyes left the bag, though, they couldn’t but wander back to his mother’s exposed thigh. Thoughts of what could be further exposed raced through his mind.

Perhaps sensing a mutual… discomfort, the two of them called it a night, though not before Jamie expressed one more time how much this meant to him. A little awkwardness adiosbet güvenilirmi aside, Jamie was beyond thrilled at how supportive his mother was being. They went to bed happier than any other time in either’s recent memory.

For Jamie, though, those feelings shifted slightly when he sat down for breakfast the next morning and was soon joined by his mother clad in nothing but a pair of tight, purple hipsters and a matching bra.

“Morning, Jamie. Is something wrong?” she asked, hiding a wolfish grin behind her coffee mug as she took a seat at the kitchen counter.

It took a few, long moments for Jamie’s brain to de-fry, but he quickly decided the change in scenery was nothing to complain about.

“I’m going to give you the same advice a wise, elderly woman gave me just recently: You do you.”

Whether it was her son’s nonchalance about her partial nudity, or the elderly comment, the boy wasn’t sure. Either way, he delighted in the souring of her half-hidden smirk.

Not one to back down so easily, though, Julia decided in that moment she’d be spending the rest of the day as she was: scantily clad. Nevermind the fact that it had taken her a full hour to work up the courage to actually leave her bedroom as she was.

The rest of breakfast was a bit stiff. No, not in that way. Well, slightly in that way. The conversation was stiff and the cause of that stiffness may have been a separate sort of stiffness.

Admittedly, Jamie wasn’t thrilled about eating breakfast with an erection, but he got used to it quickly enough. When the meal finished, Julia went straight to the living room in her underwear, while slunk away to his room.

Julia thought when her son retreated, the battle was won. She had proven herself the cooler cucumber, after all. So, it was to great surprise that Jamie returned to the living room in one of the less-than-outfits she’d given him the night prior. Once again, she had to exert fairly strenuous effort to not to stare at the cute, little bulge in a pair of panties. This pair was another thong, but lacy and a deep magenta that looked wonderful hugging his wide hips. The matching bralette on top wasn’t exactly supporting anything, but it certainly made for a look.

Julia had to wonder if she had some instinctual insight into the boy’s tastes. It couldn’t be a coincidence that he was wearing the hell out of everything she bought for him.

After the initial titillation of hanging out in their underwear died down a bit, Julia and Jamie found themselves just… hanging out. In their underwear. Neither of them were particularly cognizant of whichever HGTV show was on, but they caught bits and pieces of it. Something about two partially employed cryptozoologists with a budget of $4 million. The usual. Halfway through the episode, Julia made an observation.

“So,” she began. “Is it just me, or is this kinda nice?

“It’s definitely not just you,” Jamie assured her. “It’s fun. Plus, you’re hot and I’m… here.”

“And hot, Jamie. Don’t be obtuse.”

“Ooh, there’s something there with acute. Gimme a sec.”

It took Jamie much longer than a sec, but he eventually constructed a semi-decent joke. As a side effect, blood started flowing out of his bulge and back into his brain. With all that extra brain blood, Jamie really thought about the situation and found he was happy. He felt like himself. He felt safe. He felt… sexy.

Jamie and Julia lounged about in their underwear, watching HGTV for another two hours. They simply enjoyed each other’s company and ruthlessly mocked the awful taste of everyone on TV. Two hours turned into a few more, turned into lunch, turned into dinner, turned into a whole day. When the time came to pack it in for the night, it was with a smile, an “I love you”, and a peck on the cheek.

Come morning, Jamie was pleased to find his mother sitting at the kitchen counter in a similar getup. To his delight, she’d opted for an even skimpier pair of undies this time. The sky blue g-string left little to his devious imagination. For his part, he’d decided to wear his new crop top, sans bra, plus the strawberry thong he’d worn the first night of their new dynamic. Julia made a mental note to take the boy out for underwear shopping.

“Nice butt,” the boy commented.

His mother swatted at him playfully. That was bolder than she’d expected, but she couldn’t deny the jolt it sent through her.

“And you’re one to talk? The bottomless look tends to emphasize a certain feature.”

She gave a pointed look at the boy’s own exposed bottom. Jamie giggled and sat down for breakfast.

“Any plans for this fine Sunday?” he asked.

“Not if they involve clothes,” his mother replied with a mischievous grin. Before Jamie could comment on that, she continued, “I could certainly work on my tan, though. Care to join me in the yard this afternoon?”

It took a moment for Jamie to realize she wasn’t trying to get him to weed the garden again. Though he agreed at first, Jamie ended up getting distracted looking for new underwear online, so he didn’t join his mother until later in the afternoon, an hour after she got started. He walked out the back door to find his mother sprawled out on a lawn chair beside the pool. The yard was mostly pool. Thus the joke.

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