Dante is 18, Sicily is his mom, so… and Logan is 20
Also, mind the tags. This story contains cross dressing, feminization and incest. If that’s not your thing this story is not for you.
Dante rushed home from school in his mom’s Volkswagen Beetle, happy to be free from another week of stress. He parked in the driveway and entered his luxurious home that he would have to himself for the weekend. His mom was on another vacation with her new girlfriend, Logan. He was glad his mom seemed to find happiness, but in the times they went out of town together, he was just thrilled he was home alone to enjoy the freedom.
He sped up stairs to his mother’s room while simultaneously connecting his phone to the blue tooth speaker. Moments later the house was filled with loud music from his “girl power” playlist which featured songs from Beyoncé, Katy Perry, Lady Gaga, Rihanna and the like.
He stripped and left his clothes on the floor while he searched her room for something pretty to wear. He had discovered long ago that he and his mother wore the same size clothes. Even her tops would fit him because she was rather flat chested herself. He settled on a white, spaghetti strapped mini sundress with pink flowers on it and a pair of pink, lace panties.
He laid the outfit on the bed and took a look in the body length mirror on the inside of his mom’s door. He had been dieting to maintain a slender frame and it was working. He was naturally short for a guy at only 5’6″ and weighed no more than 115lbs.
Mixed with Black and Italian like his mother, his skin was a tan and his hair was medium length, brown and very curly. Sometimes he wore his hair down and straight but never during the school year to avoid ridicule. If he shaved off his thin mustache and wore his hair straight he could easily pass for a girl, which was desirable for him but not in front of his classmates. But other than his head, he was completely shaven smooth.
He swung his hips to the music in the mirror, throwing his hands in the air and twirling around, trying to mimic the moves he had seen girls do on t.v. and at school dances. He gave himself a B+ on his moves and then exited the room naked, headed to the bathroom in the hallway rather than his mom’s en suite.
He liked to feel the cool air on his bare skin and he especially enjoyed the faux danger of being caught walking around the empty house without clothes on. Often he even fantasized about being caught either naked or in panties by his mom, who would get so turned on by his femininity she had no choice but to take him. In some iterations, he’d be a willing participant, in others, an innocent little puppet of his mom’s ravenous lusts.
It was an absolutely absurd fantasy that he was sure would never be fulfilled, but it didn’t stop him from stroking his little cockette imagining it until he came all over himself.
He skipped into the bathroom, leaving the door open and the music blaring, humming the lyrics to “Naughty Girl” by Beyoncé. He washed and dried quickly and returned to his mother’s room, eager to finally get fully dolled up after a two and a half month long wait.
He usually wore a pair of his mom’s panties from the hamper underneath his boy clothes when he went to school. Since mom did laundry every Friday like clockwork, he would steal a pair of dirty panties either Saturday or Sunday, wear them throughout the week, and return them Thursday night or Friday morning before she noticed they were missing.
Only when she was out of town could he wear a fresh pair, wash them and put them back where he found them, not to mention the fact that he could wear her full outfits.
Dante sat in the little chair at his mother’s vanity table, looking down at the many products she had accumulated. He decided against a full makeup job since he screwed it up so badly the last time he looked like a clown. He settled for simple pink lipstick and nail polish that would accent the dress. He then spread lotion and sprayed perfume all over his body and put on the panties and dress.
He was surprised at how short the dress was. It barely reached mid thigh and he figured it was shorter on him since he was a couple inches taller than mom. He whirled in the tall mirror again, his pretty dress flying in the wind, slightly exposing his panties, making him feel a little naughty. He then left the room, turned off the music and sat down on the couch downstairs.
Dante felt like such a pretty girl in his short little dress with his legs crossed, his little pink toes in the air, his soft panties snuggling his little penis in. Nothing felt more freeing, more natural, more sexy. Completely comfortable on the couch after a long day at school, Dante drifted off to sleep, unable to hear the key unlocking the door.
Sicily couldn’t believe it. Two days into her trip to Mexico with Logan and they break up. How the hell did this happen? Sicily asked monsters of cock porno herself as she sat in the back seat of the Uber and went over last night’s events in her head.
She wanted to take a step forward in her relationship with Logan so she gave her a key to the house. Then, for full disclosure, she had warned her that her son, Dante, was still living there. And that’s when Logan flipped out and left her there in Mexico.
On their first night together six months ago, Logan told her she only dated ‘true lesbians’ – those who had never slept with a guy before. But being a little buzzed and really horny that nigh, and Logan being the most gorgeous woman she had ever seen, she neglected to mention her son and his dad, figuring they’d never see each other again anyway.
But they did see each other again. And again and again. They couldn’t get enough of each other’s bodies. The sex for both of them was mindblowing, way better than anything they had ever experienced. And before long, a friend with benefits became her true love, or so thought Sicily.
But still she held on to hope. She hadn’t been able to contact Logan since she left her phone when she stormed out, but Sicily believed that if she could just explain herself, she would make her understand and things would go back to normal. Surely Logan wouldn’t throw our relationship away over one stupid mistake from 18 years ago, she reassured herself as the Uber pulled up to her home.
Sicily resolved that she’d just get some rest and that Logan would probably come to her senses after she had time to sleep on it, and then she would visit her tomorrow. She towed her luggage from the street to the front door and inserted her key, turned it and pushed the door open.
“Tae, I’m home early,” Sicily announced loudly into the dimly lit house. “If there’s a girl in the house this is your chance to sneak her out the window!” No answer, he must be asleep, she figured as she walked past the living room and up the stairs, dragging her wheeled luggage behind her.
When she got to her room she stepped on something when she walked over to put her bags on the bed. She then turned on the light and looked down. Dante’s school uniform, beige kakhis and burgundy polo shirt, and also a pair of panties. So he did bring a girl in the house. Good for him but why is her underwear in my room? Oh my god, did they fuck in here?
Sicily looked at her bed which was still perfectly made up and then checked under the covers for wetness. Nothing. Maybe they’re in his room, still in bed she thought as she headed that way. The prospect of catching them in the act was exhilarating for some odd reason. But the door was open and the room was empty.
She came back to her own room and examined the very familiar looking panties on the floor. Red and white striped bikini panties, identical to the ones she had on the night before she left for Mexico. Did he use my panties to masturbate? She wasn’t grossed out by the thought. In fact she was a little flattered that a handsome young man would get sexual satisfaction merely from her unmentionables, even if it was her own son.
She resolved that she wouldn’t berate or tease him about it but just have a candid conversation with him. That is, when she found him. She came back down stairs looking for Dante in the dark house when she spotted a figure on the living room sofa. The first thing she could make out was hot pink toe nails, followed by smooth, shapely legs.
Sicily’s eyes slid up the apparently female body all the way to a short mini dress and the pillow that covered the girl’s face. Dante left this girl on the couch alone? Where could he have gone?, Sicily wondered. So maybe those were her underwear in my room. So that means… her heart thumped at the realization that this girl was alone on her couch with a tiny little dress on that had ridden up just shy of her probably bare crotch.
She bit her lip hard, trying to shock herself out of her horny mental state. She knew it was wrong to be lusting after this young girl, probably Dante’s girlfriend, while she slept and she tried to clear her dirty mind. But after being deprived of sexual fulfilment during her short stay in Mexico, she couldn’t help herself and rationalized that she could just take a little peek as long as she didn’t wake her. No harm, no foul.
Sicily tiptoed over to the front of the couch, overlooking the sexy silhouette. She held her breath as she gingerly slid the front of the girl’s dress up the last inch, slightly uncovering pink, lacy panties. Surprised by the appearance of underwear, she pondered the confusing situation.
Ok, so those were my panties up stairs. But if there’s a girl here why are they even out? Tae wouldn’t be masturbating with a girl here. Right? And where the hell is he? Sicily gave up and decided to ask the girl where her son is, wanting answers but partly hoping to see if the girl’s naught america porno face was as beautiful as her body. She took the pillow off and was startled after a few seconds when she made out Dante’s face, touched up with pink lipstick.
The sight took her breath away. Her little boy, lying there on the couch, hands above his head, dressed in a pretty little dress and wearing panties, sleeping serenely. And rather than being turned off by the realization that this was a man she was looking at, and her son nonetheless, it gave her tingle between her legs.
She had never seen a guy look so appealing. It was bizarre to her that he had this effect on her, as if a simple dress crossed wires in her brain that pushed her sex drive past all natural barriers. Sicily had half a mind to drop her shorts and play with herself right then and there while the other half screamed, this is your son, sicko!.
And so she stilled herself, her motherly instincts winning over her libido and she shook Dante to wake him. Knowing him to be a hard sleeper, she sat beside him on the couch while shaking him at both his arms. It took a while before he would finally stir and wake, opening his eyes.
“M… mom?” he whispered in a groggy little voice, apparently too out of it to realize what he was wearing.
Sicily smiled at the cuteness, he was like a little kitten. “Hey there, pretty.”
Pretty? Did she say pretty? Why would she… oh shit! Dante’s eyes went wide at the realization he had been caught. His heart rate skyrocketed and his mouth went cotton dry. “Oh my god, oh my god!” he exclaimed as he covered his face in shame and put the pillow over his crotch and cringed down, trying his best to just sink into the couch in retreat.
“Its ok, Tae Tae. You don’t have to hide from me. I think its kinda cute, actually,” Sicily giggled as she wrestled the pillow away from her squirming son. When she finally removed the pillow, Dante just covered his face with both pink nailed hands as if it would make him invisible.
Calling him “pretty”, “cute”, and “Tae Tae” whilst giggling hardily wasn’t the best way to convince him she was sincere. She tried again, grabbing his wrists to gently pull his hands away. “C’mon, Tae, really, its ok. I’m not gonna make fun of you. I promise.” Sicily said, trying to quench the slight amusement in her voice. Amusement brought on by his futile efforts to hide rather than the way he was dressed.
“No! You’re already laughing at me! Just… go somewhere and let me change, ok!”
“No, sweetheart. I’m not going anywhere. Just look at me so we can talk,” she finally managed a sincere tone. Dante didn’t remove his hands from his face and he refused to talk. “C’mon kiddo, its not like I can’t see you. Your nails are still pink, you still have on a dress and thanks to all your wiggling, I can see your pink little panties.”
Dante’s hands shot down to pull his sundress down to cover his undies, almost as an instinct of feminine modesty. He then looked up at his mother, smiling beautifully over him, her long, curly, black hair framing her lovely face, her expression giving him the comfort of assurance her mere words failed to. His mother was a beauty queen in his eys, with full, glossy lips, hazel eyes, and smooth, milk chocolate skin.
“Ok, so can we talk now?” Sicily asked.
“I just wanted to say I’m not mad and there’s no reason to be embarrassed. And I wasn’t laughing at you as much as just laughing at the situation. But, really, I think it’s good that you want to experiment with girly clothes. I mean, it’s not the worst thing to try. It could be drugs or gangs or some weird ass religious cult or something. So I’m not going to act like a pair of panties is the worst thing ever. Especially when you look so good in them.”
That part was a little risky, Sicily ruminated as she tensed up waiting for his reaction, relaxing when he smiled.
“You… you really think so?”
Dante furrowed his brow. “So… do I look good as a boy or as a girl?” he asked shyly.
Sicily thought for a moment. He looked sexy enough as a girl to wet his own mom’s lesbian puss, but what if he wanted to be appealing to straight girls… or gay guys? Was he gay? Not wanting to offend him either way, and trying to ascertain more info, she said, “I think you’re beautiful as you are. But which do you want to be? Like, what made you want to dress like a girl in the first place?”
“Well, it started when me and Taylor became friends. I had a crush on her, or I thought I did, but I realized I didn’t want to be with her, I wanted to be like her. She was so cute and soft and girly and sexy and all the boys wanted her. I wanted to know what it felt like to be a pretty girl, so one day I put on some of your stockings, another day a bra, and then… well, here we are.”
“Hm,” Sicily thought, drawing a conclusion about his nubiles porn orientation based on context clues, but sensing he didn’t want to come out and say it, she didn’t press the issue lest he shut down again. That part would be a conversation for later. “So, this wasn’t your first rodeo. Y’know, when I found my panties on the floor up stairs, I thought you might be masturbating with them.”
“Nope, just wearing them,” Dante lied, not ready to spill that part of the story. It was one thing to be wearing his mom’s panties and another to be wanking his cockette while sniffing them. He figured a half truth would suffice for now… or forever.
“I see, so how often do you wear my clothes?”
“Well, I wear your panties almost every day. I only do a full dress up when you’re on vacation because I was always too scared to get caught.”
“Well, there’s nothing to be afraid of, sweetie. You don’t have to wait until I’m on vacation to dress up. I think I’ll like having another pretty girl around the house,” Sicily assured as she caressed his cheek.
Dante smiled. His mom thought he was pretty. The thought warmed his heart but he began to wonder how he got caught in the first place. “I’m glad you came back when you did. I would have never thought you would be so cool with all this, but, weren’t you supposed to be on vacation with Logan? What happened?”
Sicily took a deep sigh, dissapointed she had to shift her focus from her sexy son to her failing relationship with her probably soon-to-be-ex girlfriend, Logan. It also made her realize how wet her panties were when she stood up to walk to the kitchen. “Wine?” she asked as she re-entered the room and sat two glasses on the coffee table.
Dante sat up and watched his mother pour the glasses of white wine, still awaiting an explanation as to why she wasn’t sunbathing in Mexico. His gaze shifted from the glasses to the legs of the woman pouring them.
She was wearing grey jean short shorts and he fastened his eyes on her fleshy thighs which he had fantasized about getting his mouth on plenty of times. Her upper body was very thin and dainty, with A cup tits and a really thin waist, but her lower body was very shapely, with hips that gave her an hour glass shape, and a nice, round behind.
Dante’s cock swelled in his panties as he watched his sexy mom, queuing him to cross his legs to hide it. Sicily handed him the glass of wine, took hers and sat beside him. They sipped their wine and poured more as she told him about the trip. How she wanted to take their relationship to the next level and how it ended with Logan disappearing, leaving her in Mexico.
Dante comforted his mother, telling her how much of a bitch Logan is and how stupid she is for leaving her. He then began to tell her how sexy she was in very inappropriate ways, complementing her on having the “prettiest little titties” and a “sweet ass”. He even went as far as to say he knew she had a juicy pussy because of how he found her panties.
Sicily couldn’t stop laughing and blushing, squeezing her thighs together as to signal her pussy to stop drenching her panties. It didn’t work. At one point she wondered if he might be able smell her arousal. If this was a girl from the bar, she was sure she would have ripped her clothes off already. But it was her pretty little gay son. Completely off limits in so many ways.
But that didn’t mean she couldn’t complement him which she did every chance she got. She told him how much of a cutie he was and how sexy he would look in some of the different outfits she had upstairs, and even mentioned a few lingerie pieces she thought would compliment him. He had asked her to do his makeup one day and she promised she would, but not tonight because of their current mind state.
Dante seemed to become an entirely different person when he was drinking. But she had to admit it was a lot of fun to hang out with Tae Tae for the night as they talked and joked and cried and laughed.
Once all their commotion had dissipated, they reclined on opposite ends of the couch, massaging one another’s feet.
The two luxuriated in the soft touches, sighing softly as they relaxed. They weren’t necessarily drunk but several glasses of wine had given them both a constant stimulating buzz through the night. Neither Dante nor Sicily let on how turned on they were, sure the other was totally disinterested for issues of orientation and the fact they were related.
But Dante’s cock remained stiff and dripped precum all night. If it hadn’t been for his underwhelming size, Sicily would have surely noticed him poking out, tenting his sun dress, but it remained arrested in the pink, lace panties. So, they restrained themselves, though driving each other mad with lust through words and touches until they both fell asleep.
A beautiful goddess, soft hair flowing, curvy hips rocking, sauntering up to the white shore from the cool, blue ocean. The figure approached Sicily from a distance as she sat in the sand, legs spread wide awaiting the woman she instinctively knew was her lover, whose mission, so it seemed, was to give her pleasure. She radiated a kind of celestial sexual energy that got stronger as she approached, sending a current through her body.