Halloween Girl

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An older gent sees a boy dressed up as a girl for Halloween.
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[Everybody's 18+.]

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.

"Was it bad?"

"I don't want to talk about it, sir. I'm not gay."

"Yes, Josh, I know you are not gay."

Silence sets it. What are youth talking about these days? Justin Bieber?

"You want to sit on my lap, Josh?"

"Sir?"

"You are dressed for it. Your pretty girl outfit."

He nods.

"I suppose I could."

I spread my legs and let him sit on my left thigh. I put my left arm over his waist.

"Comfy?"

"Yeah."

We don't say anything for a while. I savor the sweet moment. I certainly didn't expect to be in this position when I woke up this morning.

His face leans towards mine. I put my other hand on his waist and draw him in closer. I let him close the gap, bring his pretty face to mine. I press my lips against his. He's kissed before and wants to be kissed now. I keep the kissing at lips level, and he's happy to follow my lead..

After a long while I break from the kiss and look at his pretty face, I see his emotions are high. I bet his dick is as hard as wood right now.

"You're so not gay, Josh."

He giggles embarrassed and shakes his head.

"No, sir, am not."

I kiss his sweet lips again.

Not long after, he leaves my place. He tells me he's going to slip into his house through the back so that his parents don't see him.

***

It's December already. It's 11 a.m. and it's a bright day, made brighter by the snow covering everything. I shovel some off my alley when I see the boy -- Josh.

"Good morning, Mr. Brown!"

"Good morning, Josh! How are you today?"

"Great, really. I thought I'd get out of the house and take advantage of this sunny day."

"Good thinking."

"Well, actually, I wanted to come to see you. Maybe do a little something around your house."

"Are you asking me for a job, Josh?"

"Nothing like that, sir. I don't want any money. Maybe you could show me something. Repair work, anything really. Happy the shove the snow for you."

He's dressed in his regular boy clothes, with his hair under his wool cap. It's the same pretty face from Halloween.

"Why don't you get inside, buddy? Better like that."

"Sure thing, sir."

"I'll finish what I've started here and be with you in ten, fifteen minutes. Okay?"

"Yes, sir."

Back in the house, I put my jacket on the hanger by the door. Josh's jacket in waiting there already, as is he, sitting straight on a chair by the large dining table. The living receives plenty of light through several window panels.

"I'm gonna eat. I have soup and cold turkey. Care to join?"

"Yes, please."

"Actually, there's plenty more in the fridge, but I can't be bothered to fix or heat anything but the soup. You're welcome to have anything you can find, though."

"No, thanks, sir. Soup and turkey is good."

The soup is thin and savory. The turkey is cold. I finish eating without much talking. Josh has eaten without making much fuss, keeping his pretty head down.

I pick up the dishes and dump them in the sink.

"I can wash those, sir."

"I can wash them myself."

"Noted, sir."

"Take your clothes off."

"Sir?"

"You heard me, sweetie."

"Yes, sir."

He obeys without further protestations and fold his clothes before placing them on a nearby couch.

"Did you take a shower today?"

"Yes, sir."

"What time?"

"Ooh, not sure. 7:30 or 8."

"Not good. It's 11:30 now. Go take a shower."

"Yes, sir."

"Wait!" I call out to him when he's by the bathroom door and throw him a fresh, folded towel. "Now go."

He doesn't take long, and when he's back I let him in the middle of the living. I ask him to turn around a few times. It's the same living with large windows.

Josh is rather smallish for a boy, with soft shoulders and pleasing girlish curves. Even his butt is shamelessly fleshy.

The house is a bit chill, I don't heat it to where it's comfortable staying in underwear. He'll be cold soon.

"Let's go upstairs. The master bedroom is warm and cozy."

I follow him up the stair. The room is large, and it too has large window panels, on two sides.

I sit by his side. I run my hand over his back, neck to butt crack. I haven't experienced this kind of pleasure in a long time.

"Sir?"

"Yes, Josh?"

"Is Missus going to show up?"

"No, Josh, she's out of town."

She's visiting a relative.

I kiss the boy. His mouth tastes fresh. He had brushed after the meal. So did I.

I eat his full lips and suck his tongue. Damn it. It's been such a long time!

I stand in front of him, caressing his facial features. So smooth, so soft. I lean forward to kiss him.

I kneel to look at him from the same height. I push his legs apart, running my hand over his thigh. The boy is smooth like a girl.

His tiny dick is hard and pointing up. I cover it and his small testicles with my right hand. Can there be something sweeter than holding a boy's parts in your hand? The smaller the better. It gives you options, hold them, grab them, pull them, all the while having it all in hand.

"Sir?"

"What is it, Josh?"

"What if someone sees us?"

The road is visible over the windows, so are the neighbors' houses.

"I got you."

I go find a party mask in a drawer, one of those lacy masks worn by women at costumed parties. I fit it on him.

"Nobody will recognize you now."

"What if they see me leaving?"

"Well... you have a point. You want to give the mask back?"

"No, I'll keep it. What if somebody sees you and spreads the word?"

"Yeah, as if I care."

The mask still leaves his lower face open, and I kiss him more -- deeply and slowly, as kissing should be done. As I haven't done it in so long. The boy responds, his mouth seeking mine back, his tongue finding mine. His arms hold me and pull me closer.

I still have his cute junk in my hand, playing it, pulling gently.

He starts flowing as our kissing gets the most intense. It's only now he moans. I don't stop rubbing his genitals, on the contrary, I try to please him. When the final throes of orgasm leave him, he pulls back. His happy, wide smile makes it all worth it.

"Sorry." he says.

"No, don't be."

"I've cum all over you."

He did cum a surprisingly large amount. I guess one cannot guess the amount of semen by the size of the balls.

I grab a white towel from a cabinet shelf and wipe his crotch, then wipe most of what dripped on the floor. I throw the towel in a laundry basket by the door.

"Won't Missus see it when she comes back?"

"I doubt she'll check for cum stains."

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AnonymousAnonymous4 months ago

You might want to try a different editor. Her/him, Josh/John, "Happy the shove the snow for you." "The living (room)receives plenty of light through several window panels." "He obeys without further protestations and fold(s) his clothes..." "when he's back I let(?) him in the middle of the living (room)." "It's the same living (room) with large windows."

Those are a lot of mistakes to miss on one short page. Aside from that, this story has no emotions and no heat. Josh/John is like a robot.

You might not be the best person to give writing advice.

wankerholic42wankerholic424 months ago

Nice one! Looking forward to reading your other stories.

jrrtolkien420jrrtolkien4207 months ago

Pretty good start.

AnonymousAnonymous7 months ago

Looking forward to another part.

AnonymousAnonymous8 months ago

Many guys have dressed up for Halloween and enjoyed it so much they continue

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