Aunt Diana Ch. 1

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Eyl 2, 2023 // By:analsex // No Comment

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“Diana, I have to tell you something,” Sharon said. Sharon had had a few, and Diana got the sense that she’d been working up the nerve for this all night.

“Of course,” Diana said. “What is it?”

“It’s about my son, Aiden. I’m worried about him sexually, and I was wondering if you could…”

“Sharon, I love you, but I don’t know that I can give you any advice on my godson’s sexuality.”

Sharon’s eyes widened. “Oh, no! Nothing like that. This is…this is different. Perhaps I shouldn’t have brought it up,” she said, looking away. “I just don’t know what to do.”

Diana noticed her friend was blushing. Curiosity piqued, she said “It’s Okay, you can tell me.”

Sharon looked around then leaned in towards Diana, her elbows on the little round tabletop. “He’s been wearing my clothes,” she whispered.

Diana almost laughed – was that it? But she could tell that Sharon was distressed, so she put on a worried expression and asked, “What?”

Sharon nodded. “Yes. And not just my dresses and blouses, either. He’s been going through all of my drawers while I’m away at work. Even my underwear drawer – I think he likes to wear my panties.”

“Oh my God,” Diana said. “Have you spoken to him about this?”

“No, of course not. He would be mortified. I’d be mortified.”

“You can’t just let him keep going through your things, Sharon. You have to say something. Really you should be punishing him for something like this. It’s dishonest and weird behavior.”

“I know, I know. But he’s nineteen, and he’s always been such a timid boy. I worry that this might scar him – you know how awkward it can be to talk about this sort of thing with your mother.” Sharon sighed. “What should I do, Diana?”

“Do you want him to stop?”

“Of course.”

“Then you have to punish him,” Diana said.

“But how? He’s too old now for me to ground or spank him.”

Diana smiled. “That’s easy. Give him what he wants.”

“Give him what he wants…?” Sharon asked, confused.

“If Aiden wants to wear women’s clothing, then let him wear women’s clothing. Make him, actually. Take away his boy’s clothes and make him wear your things around the house. Dress him up in frilly dresses and makeup, jewelry and high heels. And your bras and panties, too, since he seems to like them so much.”

“I don’t know, Diana,” Sharon said, “that seems very strange. And almost like rewarding him, too.”

“No, I think he enjoys the sneaking around and doing something naughty. If it’s all out in the open, if his hidden fetish just becomes dress-up time with Mommy, I don’t think he’ll like it very much. In fact I bet he’ll be begging you to let him have his clothes back.”

Sharon seemed to think for a long moment. “That actually does make some sense. I just don’t think I could do that, Diana. It would be too strange for me. I’m his mother, after all.”

“Then let me,” Diana said. “Bring him over to my house this weekend and let me dress him up for a few days. Caitlin is off at school right now, anyway, so I have the place to myself.”

Sharon looked so relieved that Diana hugged her.

“Are you really Okay with doing that?” Sharon asked. “I know that this is a strange situation.”

“Of course,” Diana said. “You’re one of my closest friends, always have been, and Aiden is my godson, I’m practically his aunt. I’m happy to do anything for you guys.”

“Thank you so much, Diana,” Sharon said. “Really. This has been bothering me for months now. Just one thing – could we keep this between ourselves for now? I don’t know what other people would think.”

Diana laughed. “It’ll stay between you and me, don’t’ worry. And your son, too, I suppose.”

They both laughed, and Sharon hugged and kissed Diana on the cheek. Diana could tell how happy and relieved Sharon felt, and over dinner and more wine they hashed out the details. Sharon would drop her son off on Saturday on the pretext of Diana needing help around the house, then return a few days later when Diana told her that Aiden was ready. He would not have a suitcase, and Diana hoped to get him out of his boy’s clothes as quickly as possible and mail them back to his mother. He’d be naked and on his own, with nothing to wear but Diana’s lingerie and dresses. Then the “punishment” would begin.

Sharon dropped Aiden off a few days later and Diana met him at the door. She looked him over as he stood awkwardly on the porch. He had Sharon’s bright blond hair, grown a little long for a boy, perhaps, as well as his mother’s full lips and big blue eyes. A good-looking boy, she thought, though slight – he was taller than Diana was even in her stiletto heels, but she almost certainly outweighed him – and a little shy. The girls at school probably tormented him – he was more feminine than a lot of women. He probably looked good in women’s clothing, though, she thought, and smiled. They would find out soon enough.

She led him into the sitting room and sat down across from him. There was a gift bag on the Kars Escort coffee table between them. She crossed her legs.

“Do you know why your mother brought you here this weekend?” Diana asked.

“To help you around the house?” Aiden said. “I dunno, she didn’t really tell me.”

“Well, that’s partly true. You are going to be helping me around the house. A lot, actually but that’s not why she brought you here.”

Aiden looked confused.

“Why don’t’ you open that gift. It’s for you.”

Aiden reached into the bag on the table then stopped when he felt what was inside. He looked at Diana with questioning eyes.

She nodded. “Go on.”

He continued and pulled out a flimsy silk nightgown. It was purple with white lace on the chest and fringe, and little spaghettis straps at the shoulders. He held it up and looked at it, stunned.

“What is this?” he asked dumbly.

“It’s a nightgown. A women’s nightgown, for you. Now do you see why your mother brought you here?”

Aiden shook his head but he was blushing terribly.

“You don’t have to play dumb,” Diana said. “Your mother told me all about your little habit. She’s worried, you see, and I can’t blame her. What kind of boy likes to wear ladies’ underwear? His mother’s underwear, no less.”

“I d -“

“Don’t try to deny it, Aiden. She knows. She has known for weeks. Did you really think she wouldn’t notice? A mother notices everything about her baby. And she’s told me ALL about it.”

Aiden said nothing, just stared intently at the floor.

“Yes,” Diana continued, “and your mother has had enough. She said, ‘If he wants to dress like a girl, then let him dress like a girl. That will put a stop to this.’ This weekend is supposed to be your punishment, Aiden, and there’s no way out of it. If you don’t cooperate with anything I say then she is sending you to military school. Do you want that?”

Aiden shook his head. He looked like he was about to cry. Diana sat next to him on the couch and rubbed his shoulder.

“But I disagree with your mother. I don’t’ think this has to be punishment at all.”

Aiden looked up.

“No,” Diana said, “What I think is that you’re going to like this, aren’t you? This wouldn’t be a punishment. Sharon, your mother, doesn’t understand that some boys just want to be treated like little sissies, and dress up in frilly panties and bras. I think you’re a sissy, Aiden, and if you want me to then we can make this weekend very fun. I can teach you all about dressing up and putting on makeup and jewelry, all the things that girls have to know, and then I’ll tell your mother exactly what she wants to hear. All you have to do is tell me the truth – that you want it.”

Aiden slowly shook his head. Diana stood up.

“I know this is a lot to think about. But if you don’t want to be honest with me you’ll still have to wear women’s clothing, Aiden, and it won’t be fun, and you may still end up at military school. I’ll be up in my bedroom. Come tell me what you decide.”

Diana left the sitting room and went upstairs and started getting dressed for bed. She was in her own nightgown with her dark hair done up in a bun when she heard a soft knock at her door. She padded over in her bare feet and opened it to see a bashful Aiden standing in the hallway, the purple nightgown in one hand. She crossed her arms. “Well?” she asked.

Aiden looked down at Diana’s manicured toes. “I…I want to do it,” he said softly.

“Want to do what?”

“I want to wear your clothes, Aunt Diana. I want to be your sissy.”

Diana smiled. “Good. I’m proud of you for being honest. But if this is going to work you’ll have to be more than honest. You’ll have to do exactly what I say, when I say it. Do you understand?”

Aiden nodded.

“Now get undressed.”

Aiden balked, but Diana reminded him of their agreement and his mother’s threat. Soon enough his clothes were folded neatly in a chair and he was standing naked in the middle of the room, his hands cupped over his genitals.

“I can’t have you being shy around me, Aiden,” Diana said, “it’s just us girls this weekend, remember? And you’re going to be undressing in front of me a lot.”

Aiden slowly dropped his hands and Diana looked at what he’d been hiding. Pretty, she thought, like the rest of him. Which was good – she’d rather have an attractive naked boy in the house than an unattractive one.

“Lift your arms,” she told him, and slipped the purple nightgown over his head. She stepped back. “Looks good,” she said. “Does your mother have any nightgowns this nice?”

Aiden blushed.

“Kneel,” she told him, “right there on the rug. And close your eyes”

Aiden obeyed without question, and Diana noticed a growing bulge under his nightgown. So he likes being told what to do, Diana thought. That’s good. She pulled her phone off her dresser and snapped a picture. Aiden’s eyes opened at the flash.

“Relax,” Diana said. “I’m just sending this Kars Escort Bayan to your mother so she knows things are going smoothly. Now go to your bedroom and rest up, we have a big day tomorrow. Leave your other clothes here.” She smiled and looked at him. “I’m proud of you.”

Diana said goodnight to Aiden and went to bed herself shortly thereafter. A little later she heard a ping from her phone: a message from Sharon. “great! love you :)”

The next morning Diana woke up early and got dressed and laid another outfit – a black lace bra and panty set with a garter belt, sheer stockings, a simple blue shift dress with white polka dots, and black stiletto pumps – out on the bed for Aiden. She ate a light breakfast and then woke Aiden and brought him to her bedroom. He was still bleary-eyed and disoriented when she told him to take off the nightgown, but he did so with only a slight hesitation and stood naked in front of her. He was covering himself with his hands again, but she decided to let it slide – he didn’t know it, but he’d be naked for a while yet that day.

She saw him notice the outfit on the bed. “Yes, that’s for you. But not just yet. No, being a girl is hard work Aiden, and a privilege. You’ll have to earn it. And we’ll start,” she turned and picked up the high heels from the bed, “from the ground up.”

She handed the shoes to Aiden and told him to put them on. Not surprisingly he was little wobbly in 4-inch heels, so she made him walk a few laps around the bedroom for practice, and then a few more just because she enjoyed the sight of a naked boy tottering around in stilettos. Then she stopped him, sat him down on the bed, and explained the rules for the day.

“I’ve written up a list of chores,” she said. “And as you complete them I’ll give you more of my clothes to wear. When you finish cleaning the bathrooms you can wear my black panties, dusting the upstairs, my bra, et cetera. But I will be watching you closely, and if at any point you do anything wrong or not up to standard, you have to undress and start over. Except for the shoes because I want you get to get as much practice walking in heels as possible. Do you understand?”

Aiden looked disappointed by the chores list but he nodded. Diana then led him naked through the hall and down the stairs to where she kept the cleaning supplies, smiling at the sound of his heels clicking on the hardwood. She set him up in the downstairs bathroom and explained what she wanted done, and he began mopping the floors and scrubbing out the tubs, sinks and toilets in all four bathrooms in the house. Diana would leave him alone at times and watch him at others. She especially liked watching him clean the toilets: she would make him get on all fours, his pale bum and the scuffed bottoms of his high heeled shoes pointing up in the air, and clean every nook and cranny. She could tell that this was especially humiliating for him to be watched like this, but also, based on how erect he’d get, a big turn-on.

When he got the master bathroom in Diana’s upstairs bedroom she told him to be on the lookout for a pearl earring she’d lost a few days beforehand. It was a large bathroom, so it took him a little while to clean. When he was finished he admitted that he’d been unable to find the earring, but Diana told him that was fine and that since the bathrooms were sufficiently clean he could be rewarded with a pair of panties to wear. He was obviously very relieved to hear this, and Diana thought, as Aiden eagerly stepped into the sheer black underwear, about how even a tiny piece of lacy fabric can seem like a lot of clothing when you have nothing else to wear.

Aiden moved onto dusting the upstairs, a quicker job than cleaning the bathrooms, and soon enough he had a bra on to match his panties as he began vacuuming. Diana left him to use the bathroom and noticed something while she was in there. She came out to her bedroom and called for Aiden. He stopped vacuuming the other room and came in. Diana was sitting in the chair in front of her vanity, the back of her head reflected in the large round mirror.

“Aiden,” she said sternly, “what is this?” She held up something small and shiny – her missing earring.

“I’m sorry, Aunt Diana, I must have missed it.”

“You must have missed it? Aiden, it was right on top of the sink. What did I tell you about messing things up this morning?”

“That I would have to take my clothes off.”

“That’s right. That’s expensive lingerie, and it’s a privilege for you to wear it. Now come on, get undressed.”

Aiden unhooked his bra and handed it to her, head hung in shame.

“The panties, too, Aiden.”

“Yes Aunt Diana.” He slid the panties down his legs then had to struggle for a moment as they got caught on the heels of the shoes.

“Hurry up!” Diana yelled at the flustered, very naked boy.

‘Sorry! Sorry,” Aiden said, and handed her the panties as well. Then he turned to leave.

“Just where do you think you’re going?”

“Uh, Escort Kars back to the vacuuming…”

“Did I tell you to leave?” Diana demanded.

Aiden seemed to understand. His shoulders slumped. “No Aunt Diana.”

Diana sighed. “I am doing a lot for you this weekend, Aiden. Taking you into my home, letting you wear my very nice things, helping you with your mother. We can’t have this kind of attitude. I didn’t want to do this, but you’ve left me no choice. Come here, Aiden. NOW.”

Aiden approached her nervously.

“Come on, get over my knees,” Diana said.

Aiden complied, likely knowing he had no choice, his pale butt bent up towards Diana, his rapidly hardening cock pinned between her thighs.

Diana looked down at him and laid one hand on his bare bottom. He flinched when she did so and she felt an involuntary thrill of excitement. It had been a while since she had spanked someone. “Did your mother ever spank you?” she asked.

“When I was little,” Aiden said.

“Good. Naughty boys need to be spanked.” She wound up and smacked one cheek with her bare hand, hard. Then the other. Then the other again. She built up a rhythm. Aiden took it stoically at first, but soon he began to moan and squirm. His butt turned bright red. Diana’s hand began to hurt eventually so she grabbed an old wooden hairbrush from her vanity and began to use that, making deeper thudding sounds than her hand had, and she knew he’d be feeling the hairbrush for days. Aiden began to cry, probably as much from the humiliation as from the pain – this was certainly more than he’d bargained for.

After a few minutes Diana stopped, and rubbed Aiden’s cheeks gently. She felt good, though she knew he didn’t. That had been fun. His ass was burning hot to the touch and she let her hand linger. Tears were in his eyes from the pain, and she noticed that his erection had subsided. But still, his punishment wasn’t over. She let him stand up.

“I don’t think a naughty boy like you is suited for women’s clothes or women’s housework right now,” Diana said. “I think you need to work outside. Yes, dressed exactly as you are. Don’t worry, I have high fences. The neighbors won’t see you. Probably.”

She led him outside and started him cleaning the pool. He was wobbly on the pool deck in his heels, and his pale skin was bright in the sun. She hoped he wouldn’t burn too badly. She sat in lounge chair beneath an umbrella and fixed herself a gin and tonic as she watched her naked godson work.

When he was finished with the pool she instructed him to get the lawnmower from the shed and begin cutting the grass in the backyard. This was a struggle for him – the stiletto heels of his shoes kept sinking into the soft earth as mowed, causing him to stumble. Diana laughed at the sight but she wouldn’t him take the shoes off. Soon Aiden was sweating. She pulled her phone out and took a picture of him from behind. She looked at it. It was a good shot, Aiden’s pale sweaty butt shining, the high heeled shoes clearly visible. She scrolled through her phone. She knew she shouldn’t – Sharon had sworn her to secrecy – but she’d had a few more gin and tonics by that point, and Aiden’s face wasn’t even visible. Screw it, she thought, and sent the picture to one of her girlfriends with the caption “my boytoy aerates the lawn while he mows.” Her phone chimed almost immediately with a response. A text from her friend “i want one! share? ;)” Diana smiled. “maybe. come over this week” she wrote back.

Aiden was finished with the lawn, and Diana called him in, her demeanor greatly softened from before. “You did a good job with the lawn, Honey,” she said. “Now let’s go get cleaned up.”

They went upstairs to Diana’s bedroom and she gave him a bright blue cotton bra and panty set to wear “for now.” After Aiden put those on Diana asked him to go into the bathroom and draw a bath for her. She undressed and put on a bathrobe as she listened to him run the water, then walked into the bathroom and felt the water. “That’s perfect,” she said, and to Aiden’s shock she slipped out her robe in front of him and into the water. He stood by the tub rigidly, his eyes going everywhere but towards Diana. He didn’t want to stare at her, but he knew from before that he shouldn’t try to leave without her permission. Diana laughed. “Relax, Aiden, you’re one of the girls this weekend, remember? You don’t have to be embarrassed around a naked lady.”

Diana reclined into the water languorously. She took a long bath, and kept Aiden periodically busy fetching things for her. She liked having him around, standing guard in his blue bra and panties, her own sissy bath attendant. She considered making him wash her hair or body but decided, based on the obvious erection straining against the thin cotton of his panties, that that might be too much for him right now. When she was finished she stood up and had Aiden hand her a towel which she wrapped around herself. She stepped out of the tub and to Aiden’s surprised she hugged him from the side, her large breasts pressing through the towel into his shoulder. She kissed him on his cheek and lingered, her hands on his back and shoulders.

“You were good today, Aiden, I’m sorry I had to spank you,” she said, her face next to his.

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