Alex Finds His Place - Ch. 01

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Sissy boys initiation to the web.
2k words
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Part 1 of the 4 part series

Updated 04/10/2024
Created 01/08/2024
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This is a fictional story. All the names, places, and situations have been made up.

No characters are under the age of eighteen (18).

After the divorce, Alex stayed with his dad while his mom moved to away to live with some younger guy she'd met. Not long after she left Alex and his dad started fighting over even the smallest thing. Although Alex realized it wasn't personal, just frustration they both had, he'd been spending more and more time away from home. Since he'd graduated high school, he spent most of the days at the mall with his friends, and nights until the early morning at the adult movie theatre, watching gay movies, or at the adult book store, checking out the movies in the back rooms or checking out the magazine and book rack.

Tonight, Alex is in one of the movie rooms at the adult book store. He's eighteen, 5'7, skinny, with his reddish-brown hair cut in a shaggy pixie style. He's wearing a light green cropped t-shirt that stops a couple inches above his bellybutton, baggy jean shorts, and black sneakers.

When the movie stops, Alex checks his pockets for more tokens. Finding he doesn't have any, or the money to buy more tokens, he decides it's time to leave. As he reaches for the door to leave the room it opens and an older man walks in.

The man looks at him and smiles, "Sorry, I didn't know this room was taken." The man is in his fifties, 5'11", athletic, with short black hair and a scruffy beard and mustache. He's wearing a sport jacket, matching slacks, a white button up shirt, and black dress shoes.

Alex shrugs. "I must have forgotten to lock it. Besides, I'm out of tokens so I'm leaving anyway."

The man sits on the bench next to the door. "I just bought some tokens, you can stay if you want to."

Thinking about the situation at home, Alex sits on the bench next to the man. "Sounds better than going home."

The man drops a token in the box to start the movie, "Trouble in paradise?"

When the movie starts Alex rests his back against the wall behind the bench. "Yeah, my folks are being assholes."

"That has to suck." The man pulls a condom from his jacket pocket, then takes his cock out.

When Alex sees the man pull his cock out, he's shocked at how big it is. "What...what are you doing?"

The man starts stroking his cock. "I'm going to masturbate. Do you mind?"

Alex shakes his head and tries to concentrate on the movie. "No...I'm good."

Alex continues to glance at the movie, then back at the mans cock, repeating the process over and over. "Do you do that a lot here?"

"All the time." When the movie stops, the man drops another token in the box. "I use the condoms so I don't make too much of a mess." After sliding the condom over his cock, he turns to Alex. "Haven't you?"

Alex stares at the mans cock and speaks almost in a whisper. "I've thought about it, but I never have."

The man smiles, takes Alexs hand, and places it on his cock, gently wrapping Alexs fingers around his shaft. "You've been interested in my cock, so go ahead." He slowly starts sliding Alexs hand up and down his cock.

Alex is surprised when the man lets to of his hand, it continues to stroke the mans cock. He can feel how it swells in his hand, his fingers unable to close around it.

The man places his hand on Alex's inner thigh. "I'm Nick."

Alex turns his focus to the movie, unconsciously stroking the mans cock faster. "I'm Alex."

Alex can feel Nicks cock starting to twitch. He closes his eyes when he feels Nick squeeze his thigh.

Nicks legs spread wider and start to shake. "That's it, don't stop, just like that."

Suddenly Alex feels Nicks cock spasm. He watches as the tip of the condom move as it fills with cum.

When his cock is empty Nick takes his hand from Alexs thigh and puts it around his shoulders. "Careful when you take the condom off, you don't want to spill."

Alex looks at Nick confused. "I'm going to take it off?"

Nick points to a small trashcan in the corner. "You can leave it in there."

Still confused, Alex carefully removes the condom and drops it into the trashcan. He sits back on the bench.

Nick smiles at Alex. "You did really good." He glances at his limp cock, then back at Alex. "You can put me away now."

Without thinking Alex carefully put Nicks cock inside his pants and zips him up.

Nick stands and hands Alex the rest of his tokens. "I hope we meet up again." He straightens his clothes. "If you ever get tired of putting up with your parents, you can stay with me." He opens the door and smiles back at Alex. "Have fun."

Alex stayed in the room until he'd used all the tokens. When he passed by the counter on the way out, the sales person called him over and hands him a bag. "Some guy said to give these to you."

When Alex gets home, he's glad to find his parents are asleep. He quietly goes to his room, closes the door, and empties the bag onto his bed. There are several magazines, a book, a cheap blindfold and cuff set, a vibrator, and a card. After quickly glancing at everything he opens the card. 'Alex, it was nice to meet you. I wanted to thank you for making it a special evening. I hope you like them and make use of them. I do hope we meet again. Thanks again, Nick' At the bottom of the card is the link for a website and a username.

Alex can't wait, he goes to his laptop and types in the link. After looking at the things Nick had given him, he wasn't surprised when an adult sex website appears. When he does a search on the username, Nicks face appears in a small picture at the top of the screen, with several links to pictures and videos appearing below it.

He quickly samples several of the videos until he opens one where Nick, who is nude, is helping a girl in a dress, onto a table. It's when she gets on all fours and Nick pushes the bottom of the dress onto the girls back that Alex realizes it's not a girl, but a boy wearing a dress.

Unable to look away, Alex watches as Nick stands at the end of the table and appears to tell the boy to suck his cock. As he watches the boy suck Nicks cock, he quickly puts on his headset and turns up the volume. He hears the boy gagging on the large cock whenever he tries to swallow all of it. After a while Nick tells the boy to masturbate.

It's the boy who cums first, his hips trembling as he releases cum onto the table top. Seconds later he hears the boy gag as Nicks body trembles and he cums in the boys mouth. When he is finished, he pulls his cock from the boys mouth and tells him to clean up his mess. As Nick walks off camera, the boy repositions himself on the table and starts licking up his cum.

When Alex closes the video link, returning to Nicks page, he realizes unconsciously he'd been rubbing his cock through his pants, and was about to make his own mess, inside his pants. Realizing there's no time to get to the bathroom, he undoes his shorts and slides them and his underwear down to his ankles. He takes off his shirt, and as he starts to masturbate, holds the shirt against the tip of his cock.

When he does release, his whole body trembles as he lets out a muted moan. When he's done, he steps out of his pants and underwear, tosses everything in with his other dirty clothes, and sits back at the laptop.

Realizing he can't send Nick a message, since he's not a member of the site, he rushes to create a profile. Once in he sends a message. 'Hi Nick. Thanks for the stuff. I like your site.'

Before he can log off, he gets a reply. 'Didn't expect to hear from you so soon. Have a camera?'

Nervously he messages back. 'Yes, but I'm naked.'

A smiley face appears. 'All the better. Don't be shy.'

Alex looks around the room and thinks before turning on his camera. He waves when he sees Nick, fully clothed, appear.

Nick puts on his headset and smiles. "Hi cutie."

Alex speaks into his headset. "I...I thought you'd be nude too."

Nick laughs and shakes his head. "I just got back from meeting with some friends." He appears to look at something on his screen. "A couple of them are online now, I'll let you meet them."

Suddenly two other men appear on the screen, both fully dressed.

Nick sits back in his chair. "Tom, Glen, this is Alex, the one I told you about."

One of the men waves, "Hi Alex, I'm Glen."

The other man waves, "And I'm Tom."

Glen smiles. "You didn't tell us he was this cute."]

Tom laughs. "Holding out as usual. Are the parts we can's see just as nice?"

Nick shakes his head. "Honestly, I don't know." He seems to look straight at Alex. "Stand up for me."

Alexs body trembles as he stands, his hands hiding his small penis.

Tom tosses his head back, "Damn Nick, I think this one checks all the boxes."

Alex feels himself blushing. As odd as it is, it's nice to feel appreciated, even if it is by total strangers.

Glen shakes a finger back and forth. "Not so fast." He lowers his hand and speaks in a soft voice. "Alex...put your hands down and give us a twirl."

Hesitating for a moment he puts his hands to his sides, and slowly turns all the way around.

Glen nods. "Nick...he's perfect. He's cute, has a sweet little package, and a nice bubble butt."

Tom leans forward in his seat. "Nick, did you make a copy of this to send to us? Please say you did."

Nick pauses before speaking. "No need. I'm going to post it on here."

Tom nods in approval. "I'll be sure to look for it. I better get some sleep. Some of us have to work in the morning. Bye everyone." He disappears from the screen.

Glan leans forward in his seat. "I'm going too. I'm beat." He waves, "It was nice to meet you, Alex." He disappears from the screen.

Alex is still standing, trying to understand what happened. "Are you really going to post this?"

Nick appears to be doing something on his computer. "Of course. I don't doubt people will copy it to other sites as well."

Alex sits back on his chair. "But what if someone I know sees it?"

Nick leans back in his chair. "Done." He holds both hands out to his sides. "Then they see it." He smiles. "You should check it out, see what everyone will see. You definitely made a good impression with Tom and Glen." He stretches. "I think it's time for me to get to bed also. I hope you look for me again. Good night, Alex." His picture disappears.

Alex finds the new link and clicks on it. When the picture appears, although you can hear Nick, Tom, and Glen talking, he only sees himself. He watches, mesmerized, as he follows their instructions obediently. He happens to glance at the bottom of the video and sees it already has a bunch of followers and likes, and even people who have linked to it from their profiles on the same site.

When he scrolls down, he sees multiple comments. Most talk about how cute he is, and there are quite a few discussing what the individuals would like to do to him. A few talk about him wearing girls things and how he'd make the perfect daughter or niece.

In a daze, Alex takes off the headset, pushes the things Nick had given him to the other side of the bed, and crawled on top of the sheets. Before he could realize it, he is fast asleep.

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AnonymousAnonymous29 days ago

Better yet, "Alex stayed with his dad while his mom moved to away to live with some younger guy she'd met" doesn't jive with "When Alex gets home, he's glad to find his parents are asleep"! It's OK, cutie, keep at it, you'll improve. Wish I was a slutty crossdressing 18 yr old, I'd be in heaven!

AnonymousAnonymousabout 1 month ago

I liked it. Nice start of what can be a good story with a little more work.

LilStoryTellerLilStoryTeller3 months agoAuthor

Sorry about the confusion. I think I got caught up in the story and didn't pay as much attention to the rest, my uncle always talked about tokens, so i went with it. Thank you so much for the comments. Chapter 2 coming soon!

AnonymousAnonymous3 months ago

I thought that some parts were interesting and I could put myself in Alex's shoes, especially at the adult book store. Nick seemed natural and pretty realistic and I liked his interaction with Alex. I also liked how Alex obeyed the men on camera while naked.

I guess I enjoyed and visualized myself as Alex enough to not realize that the setting was mostly pre-Internet, but also could somehow support video calls. That technological hiccup honestly doesn't bother me enough to not read it. I actually loved the pre-Internet days of life. Everything was better back then. In a lot of ways, technology only made life worse.

Thanks for writing.

AnonymousAnonymous3 months ago

What year is this set in lol. Going to an adult book store with tokens but bandwidth for video calls exists? People can like video links too?

It's like an alternative dimension lol.

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