Halloween Girl
by VerbalAbuse
Copyright© 2025 by VerbalAbuse
Erotica Sex Story: An older gent sees a boy dressed up as a girl for Halloween.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma Romantic CrossDressing .
Many thanks to neuroparenthetical, who edited this story.
It’s Halloween again. The street is busy with rowdy kids running around in their costumes. I watch the show from the lawn in front of my house. It brings back memories of my childhood, of kids growing up.
There’s a girl coming down the street, a pretty young woman who’s walking my way. She must be a party goer, her outfit looks too festive. Yellow dress covered with black motifs, black round shoes, black stockings, black hair. Cute little jacket.
Then again, all the stuff is too well cut and made. Regular halloween costumes are cheap fittings that can only be worn for a few hours.
“Hello there” I say as she passes by.
She raises her right hand, barely to her elbow and wiggles her fingers.
Girls these days!
I wonder who she is, pretty as she is.
She passes by. My eyes follow.
Later that day, I drive my truck back home after picking groceries. I see that same pretty girl again, hanging out all by herself. What’s she doing?
Just two blocks from my street, there’s a little park. No more than an open area with a few trees, some park toys and a couple of benches. She is sitting on the back rest of one, with her feet planted on the sitting area.
As I drive by I wonder Why not? What’s the harm in saying ‘Hi’? I circle back, park the truck across the street from the park and walk to the stranger.
“Good evening.” I say.
She smiles, but does not answer.
“I saw you earlier, I’m Mark Brown. My house is the long, white one on the street you were walking down earlier, the one with the large spruce tree in front.”
“I’m your neighbor.” she says neutrally. “I’m a Robinson.”
The Robinsons live just two houses down the street from my place. She must be a visiting relative.
“Are you visiting?”
“Umh, no. I live here.”
“Really? Why haven’t I seen you before?”
“I’m Josh, Mr. Brown. You know me.”
“John? Why the heck are you dressed like this!?”
“Halloween, sir? Everybody wears a costume.”
“Oh, I see it now. So you decided to dress up as a girl.”
“Yeah, that was the general idea.”
Something tells me it’s not that.
“Better come to my place before you get recognized. Some folks might take it the wrong way. And hanging out all by yourself in the park? Dressed like that? You know it’s dangerous.”
“I suppose you’re right, Mr. Brown. Wait. Are you alone tonight? I don’t want to be recognized.”
“Wife’s visiting a friend.”
Sonja -- that’s my wife’s name. She’s fifty six, four years younger than I am. We get along just fine, but love left the nest a long time ago. She lost her shape early on, and I lost interest. There had been no love making for the last decade.
Back at the house, I lead her in.
“You look like a real girl. Great job with the costume.”
“Umh, thank you, Mr. Brown. Mr. Brown?”
“What is it?”
“Please don’t tell my parents. I mean, it won’t be the end of the world if they find out. They won’t throw me out or anything, but I think they’ll freak out.”
“No worries.” I say lightheartedly. “Your secret dies with me”
He sits on a large chest on a small passageway between living and the kitchen.
“Are you cold or anything?” I ask. I sit in front of him, studying him closely. He’s pretty as a girl and sweet as a girl. Not saying he looks like a girl, though his figure is soft and feminine.
“No, sir. I’m good.”
I get closer, close enough that we almost touch.
“Sir...?”
“Yes, Josh?”
“What are you doing?”
I’m watching him. He’s so pretty. He’s young, fresh and sweet ... or maybe I just haven’t got some in too long.
“That’s a pretty outfit, Josh. Where did you get it?”
“In town. The big mall.”
“You picked it all by yourself?”
“Yes, sir.”
“You seem knowledgeable. You must have done lots of clothes shopping before.”
“Sir?”
“Yes, Josh?”
“What are you going to do?”
He’s not inviting me or anything, he’s half concerned. Ever the old fool, I can’t stop myself from toying with him a bit. I’m not a sadist or anything, I just find his nervousness cute.
“Are you gay, Josh?”
“No, sir! Of course I’m not.”
“Then why are you dressed like a girl, Josh?”
“It’s Halloween, sir. It’s just a costume. I swear.”
“You know how to wear it.”
“Umh.”
“May I examine it more closely?”
“Ooh, I don’t know...?”
His dress looks quite fine. The fabris is high quality. The design is intricate, the cuts are precise, and its many seams are strong. It has two, maybe three layers. The rest of his outfit is equally well-made.
“It must have set you back a fortune.”
“Ooh, I saved up some money for it.”
“Seriously? You saved up for it? How long did that take you?”
“Most of the summer. I spend most of my money on clothing.”
“Aaah! And you’re still not gay.”
“No, sir, I wouldn’t. Ever. I promise.”
I must have gone too far. The poor boy is scared for some reason. I sense from his voice that tears are not far off.
“It’s okay, Josh. I’ve already promised I won’t tell anybody. Okay?”
“Yes, sir.”
He breathes a sigh of relief, but I can tell his emotions are still heightened.
“You’re safe. Even if you’re not gay.”
“Thank you, sir. I really am not.”
“I know, Josh. You’re a good boy. No reason to be gay.”
“No, sir. None!”
I take his hand. What am I doing? He doesn’t pull it back.
“You’re okay. You want a hug? Just to calm down?”
He smiles. I see I was right, there are tears in the corner of his eyes. He’s calmer now.
He hugs me. I hug him back. Ah, this feels good. We stay in the embrace for a few moments, then I release him and he follows suit. I put my hands on his knees and he places his on my wrists. Maybe to stop me from pushing up.
Then I pull back. Time to give the boy space to breathe. I’d like to play with his emotions longer, but I don’t trust myself to stop in time. I haven’t played in a long time, and never with boys like him. I might fuck it all up.
“Want a warm drink? Cocoa? Tea? I have many sweetly flavored teas.”
We walk to the kitchen and I show him my wife’s tea collection. While he sifts through it, I fill and fire the electric kettle. Later we move to the living room and sit at a table.
“Have you been with a boy yet, Josh?”
“No, sir. Wouldn’t that make gay, sir?”
“Umh, not necessarily. Not if you did not want it.”
“Then, hmm, maybe something like that may have happened.”
“Once?”
“Once.”
“Several times?”
The boy nods.
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