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"Her" First Time


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It was his first time. Ever.

The idea was always in the back of his mind. He always wondered what it was like, but always knew he'd never actually do it... besides, he didn't even know where to look for one in the first place... but one day, just by happenstance, he came across a post online. Someone asking where to find one.

A glory hole.

Apparently they were a lot more common than he'd ever thought. Sex shops. It seemed so obvious in hindsight, but... he wouldn't go to one. Ever. He'd never been. Besides, this was all just fantasy. It was just porn... it was a fetish and nothing more. But no matter how much he thought about it, the idea was so incredibly hot to him. It never failed to spring an erection whenever he thought of being eye-level to a large cock. The sights, the smells, the texture, the taste... he could imagine it all, he'd even been tasting his own cum.

He was somewhat ashamed of his interests. The dirty things that excited him so much... but that shame only made it hotter, harder to resist... these feelings had already struck him once before on the way home. He'd tried hookups a few times but always chickened out as the meeting time approached.

What if his parents found out?

What if someone he knew saw him?

What if word gets out?

What if it reaches the church?

All of these questions and so many more would echo in his mind any time he started to explore it... but every once in a while, he'd have that edge-tipping thought...

How good would that feel?

That thought had so much power over him. At his most stressful times, he found him gravitating to it more and more. It wasn't what he was supposed to do. But it was what his body desired, what his body craved... he wanted to feel that shame. Maybe once the secret got out, he would be free from his closet. Maybe... that change was necessary.

There were two steps that made this a possibility. Two things he'd done recently to help stop himself from chickening out before hookups.

He'd shaved himself. Top to bottom. Only the long, soft red hair on his head remained. Having no hair on his body made him feel so much more feminine. So much more soft, so much more... slutty.

He'd bought an outfit. A girl's outfit. It was a simple one, cheap but effective. A girls'-cut shirt, a bit tight on him, but it worked; a black skirt, he loved the feeling of having so much of his legs exposed; socks that ran up his shins, something about the way they clung to his legs made him feel so much cuter; a padded bra to give him the look of having tits to fill out the shirt; hairpins to style his hair; silky white panties; and a pair of black heeled shoes, just to complete that look... The look of a horny, slutty girl who was ready to submit to anyone and everyone no matter how reckless it was...

His heart was racing just from figuring out where he'd change clothes. He briefly dismissed the idea of the bathroom. What if someone saw him walk out in girl's clothes? Then, he thought, wouldn't that be so much hotter than a gloryhole?

So, he went and changed. And she emerged.

She had decided that when he changed into these clothes, Trent was too busy studying at the school's library. It was Trish who was in town.

When she arrived at the sex shop, her heart was pumping out of her chest. She couldn't believe what she was doing. She didn't even know if they'd have a glory hole. But, she'd never been out in the public like this before, either. What if someone saw her? What if someone recognized her...?

What if, though...?

She shook the idea out of her head and continued, pushing the door inside. She was blushing like crazy. Even the clerk could tell she was nervous and asked if she needed anything.

"N-no, I'm just... looking."

It was a lie, but Trent was holding her back. He was so afraid... but why? Everyone who was here would be happy for her... She decided for now to pretend like she was just here to shop. She wound up buying a small dildo. Something else she'd never done. But there was still something there...

She was at the register, checking out... and then...

You're so close, don't miss your chance.

"Um... actually... er... n-nevermind."

Idiot.

But as she shamefully walked away with nothing but a dildo in her hand, she hesitated at the door. There was a man at the counter now. He asked about a glory hole and her whole body froze as she looked around and saw the clerk leading the man down the hallway. She didn't get a good look at the man, but that was fine. She immediately gravitated toward the two and followed them as well.

There were two doors.

"Suck on the right, get sucked on the left." 

This was it... it was real and it was here. She was frozen. Everything was lining up and she was frozen. That was when the clerk noticed her. An amused smile on her face as she gestured for her to approach.

She did. At this point, her erection was clearly visible in her skirt.

"Are you too nervous to ask? Don't be, darling. Suck on the right, get sucked on the left."

She repeated it with a wink before walking back to the counter.

Trish stepped up to the door and pushed it open, closing it behind her. Locking it. There was a stained pillow on the ground and the air in the room was humid. Her heart was racing. She'd never done this before.

The man in the other room must've heard the door close. It wasn't long at all before the cock was pushed through.

This is it.

She reached forward, placing her hands against the wall. So many disgusting things could happen... so many questions...

What if I get an STD?

What if it's someone I know?

What if they can tell I'm a guy and get mad?

He's waiting.

He acted before he could even keep thinking... so much shame filled his body as he leaned forward and licked the tip of this cock. He heard a moan from the other side. This man was sensitive. Before she knew it...

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One thing led to another. His heart never stopped pounding. The shame was so overwhelming. And yet, so hot.

This was who he was.

This is what he's been reduced to.

No man would do this.

He was a girl.

He was a slut.

And that turned him on more than anything he'd ever thought to himself before.

He.

Felt.

Good.

It wasn't long before the man came in his mouth. He didn't stop. She didn't stop, either. The man was still hard. She just kept going. Even digging his dildo out of the bag it was in and beginning to ride it, using spit and cum as lube.

And soon, it was over...? The man came one last time and pulled away. She didn't hesitate to swallow what remained. He resented the fact that he probably just sucked off some dirty old creep... somebody who couldn't get any so he just came to get a quick fix... but why did he want more?

Then one more thought returned to his head.

How good would that feel?

He heard the door on the other side open and, without thinking, without so much as moving to put her panties back on, she got up and rushed out of the door. She had to see.

She was met by a man who was smiling down at her. He wasn't leaving at all.

She blushed.

"Do you need something?"

"I-I..." She felt so small. So weak. He was so much bigger than her. He wasn't stunningly attractive or anything, but...

The man looked down at her erection, causing her to blush even more.

"I won't do a thing unless you tell me you want it."

"I-I... I do..."

"What?"

"H-huh...?"

"Would you like to come with me? Just for the night..."

Just for the night...

It wasn't just a night.

It wasn't just a night.

Again, no thoughts. He'd find an explanation later. He nodded.

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And that was how his new life began. Slowly, his shame dissolved. This wasn't her boyfriend, he was her master. He used her. She loved being desired.

And to think, all of this came, from one simple impulse.

"How good would that feel?"

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