A Stupid Bet (m+/f, nc, anal, gloryhole)

It was just supposed to be a stupid dare. With her new fake ID, she said it could get her in anywhere. Of course, there is always an asshole about, some jerk who has to challenge any claim you make. In her case, that asshole was Steve. He called bullshit on her and wanted proof. She had expected him to ask her to buy some alcohol or go into a bar, but for some reason, likely perverted, he had challenged her to go to a nearby adult theater and buy something. She was grossed out by the idea, but everyone at the lunch table had latched onto the challenge and she would have to provide a receipt for proof.

So that was how Sydney, 17, found herself outside “Handy’s” on a Friday night, biting her lower lip anxiously. She wished she had dressed super conservatively, but it was well into summer and she was going to the movies with some friends after. So, here she was, a leggy dirty blonde, wearing a modest summer dress, trying to gather courage to go inside. A car drove by and that was the push she needed. She hadn’t parked in the back, something she now regretted. Instead she pushed the black glass door and went inside.

The first thing that hit her, besides the mountain of porn, was the smell. There was a sour sweaty reek to the entire place that she couldn’t place, and it reeked of cigarette smoke. Wall upon wall of sex toys lined the back, but what drew her attention the most was some center racks. Hundreds of porn DVD’s made her want to laugh, wondering if anyone even bought those. Did they not know that shit was free on the internet?

She entered and walked inside, noticing a long hallway to her right just past some bathrooms she had no intention of using. A sign saying Booths pointed to the right and Theaters to the left. She shook her head nervously, again wondering why anyone would pay for this stuff. The toys at least she understood. She walked towards the back when a man behind a counter with dozens of old style TV’s ran behind him. Some showed porn, some showed the booth hallways and theaters she guessed.

“Excuse me miss, mind if I see your ID?” he asked. She immediately blushed, flustered as she went through her purse, her heart suddenly racing.

“Oh…um….ok..uh yeah, right, ID, right, yes sir,” she stammered, pulling out her real ID, before realizing her mistake and then switching it with her fake one. “Ummm, here you go. No problem I hope,” she said, wishing she could shut up.

“No, no. Just have to double check or I can get in trouble,” he said, smiling, handing it back to her. “Thank you miss”. She nodded and went back away from him, heart racing. Besides the man behind the counter, there were only two other men in the building. Both way older, which probably explain the lack of understanding technology. Their leers were disgusting but at least they were open about it. She always found that easier to deal with that the subtle ones, watching but pretending they weren’t.

She ignored them, and the small chime from someone entering as she looked at a couple vibrators. If she was going to get proof, at least she could get something she’d enjoy. She’d probably get teased about it, but she could generally give as good as she got. A quip about at least a toy never disappointed her would generally shut up most guys she figured. She picked out a cheaper one, hoping that it too wouldn’t disappoint, when a hand touched her shoulder.

“Sydney? Sydney Allgeier?” a voice asked, and her heart jumped, recognizing it before she turned around, pale white. Right there, hand on her, was her neighbor Bill. He was married to one of her mom’s best friends and she’d known him her entire life. And now…she wanted to bolt so bad.

“Sydney, what are you doing here,” Bill asked. But he smiled when he asked it and she was froze in place, too panicked to respond. That seemed to encourage Bill, as he slid his hand down her back, pulling her close, until his hand was resting on the top of her ass and his mouth was inches from her ear.

“Don’t worry, I won’t tell your mom, unless you give me a reason too,” he said, grasping her ass and pulling her close. She barely whimpered his name, looking up at him.

“Bill, please…,” was all she said, as he groped her ass and held her chin.

“What? We both know why you are here. Dirty little bitch needing toys? What happened to your boyfriend you fucked in the back yard last month?” he asked. She simply looked at him in shock, as he slid up his hand to her neck, squeezing the back of it firmly. “How about we have a little conversation, little girl,” he asked, though it was more a demand. Sydney found herself completely froze up in shock as he hung up the vibrator and led her to what she thought was outside.

Sydney was basically in shock as he directed her. She half expected him to take her outside to yell at her, but they suddenly pivoted and headed down the dark hallway. She stopped and looked at her neighbor, who’d always been so nice, still struggling to process the past couple minutes. He simply squeezed her neck harder, painfully and shoved her forward to the middle booth along a wall and shoved her inside. There was barely room for one person in it, much less two. There was only a stool, an old CRT TV showing static, and two rough hewn holes on each side. She’d heard of them, gloryholes, but had never seen or even thought they were a real thing. It stunk in there and she felt so trapped that she started to cry a bit.

“Listen,” Bill said, stroking her hair. “This doesn’t have to be bad. I’m not asking for much, you’re just going to be nice to me for a few minutes and I’m going to be nice back and forget I ever saw you here. Ok?” he said as he inserted some money into the booth as porn popped up on screen. Sydney just froze up, half staring at him, half at the woman getting face fucked on the screen.

“Please,” she said, before jerking hard from a sudden slap from her neighbor. That made her cry more, then he gripped her hair, pulling her down.

“No, no fucking please. Be nice or I’ll be fucking mean you whore!” With that, she was shoved down, and he pawed painfully at her chest, before slapping her several times. “The dress, out of it.” She was crying hard now, but did as he said, scared now. She pulled it over her head and he tossed it on the floor. He jerked off her bra and spun her around, pressing her face into the corner of the booth, hard against the wall as he groped her ass, jerking her thong to the side, his finger pressing hard against her asshole.

“Puh….please….I’ll…I’ll be good,” was all she could muster, barely a whisper, and the pressure relented. He turned her towards him, playing with her nipples, before mashing her tits in his hand.

“Try anything, and you’ll fucking regret it. I know what you are, understand?” he said, and she nodded. He then pushed her head down and she looked up at him, stroking his cock. “Open wide,” was all he said as he gripped her hair and pushed at her mouth. As soon as his cock was in her mouth, he began thrusting. She’d sucked cock before, but never like this. He was fucking her mouth, gagging her, drooling so bad. Then suddenly she got sick and puked a bit, but he never slowed down. Finally, after a couple minutes, she felt him stiffen and blow his load down her throat which almost made her sick again. He shoved her back and zipped up. As she tried to get back to standing a flash blinded her.

“Just proof of what you are. Don’t worry, it’ll stay in my collection as long as you behave, understand?” She nodded, when a cock was poked through. He held up the camera and told her to suck it, and though she was crying, she did as told. This guy tasted horrible and didn’t last long. He pulled back after he came, and she heard a door open and shut.

“I have an idea, stand up, face the wall. Now.” He said and she did. Her legs ached and her stomach was upset, and she whimpered as cold wetness was pressed against her ass, as he forced a finger in.

“I’ll delete my photos and video, if you let someone fuck your ass through the gloryhole. I’ll delete it so you can see its gone. And don’t worry, they won’t see you. Ok?”

She should have said no, she should have screamed, but she was so tired and scared she only nodded. She’d never done anything with her butt, but she’d seen videos and they didn’t seem too horrible. He fingered her ass a lot and then told her to spread her cheeks and lean against the wall. He pulled out a $100 bill and put it in her purse as well. She was about to ask him about it when she felt someone push against her. Then she did yell, but he covered her mouth and held her in place. Even with his hand, he had to turn up the sound of the porn to drown her out.

Hurt was an inadequate word. Her ass felt like it was on fire as the man pushed again and again. If not for Bill holding her, he would have failed but after several thrusts, the head popped in. A pill was shoved in her mouth by Bill, and she swallowed, hoping it would take her away or dull the pain. It did neither. It only made her spacey as some stranger raped her ass. He didn’t last long before dumping a load in her ass, pulling out. It hurt to move as Bill spun her about and shoved her against the wall. She cried no as another man in the opposite booth did the same, thrusting at her ass until he got in. He lasted much longer and after long minutes did he empty herself in her gut. After he pulled out, Bill let her drop as she balled up on the cum stained floor.

Bill took a dozen or more pictures, spreading her bleeding ass to take closeups of it. Then he pulled her limp and drugged body over the stool and thrust into her cunt, fucking it. She was too spaced out to do anything, just grunting as he pumped her again and again. Before long, he had filled her with his seed. He hoped she wasn’t on birth control. Then leaving her there leaking, he went through her purse, pulling out a tampon. She laid on the stool crying softly as he wiped her messy ass and cunt, then inserted the tampon in her ass. Then he helped her dress, her eyes glassy as he took her to his car. Then he took her phone and texted her friends, telling them that she wasn’t feeling good.

“You’re ruined now Sydney. No one will ever want someone like you. But I’ll take care of you. Let’s go to the motel and I can be nice to you. Otherwise, we’ll go back in and I’ll leave you in the theater. Your choice.”

Sydney could barely focus on anything, her legs ached, her ass burned, she felt ruined as he said. So she barely whispered to the man who was once her nice neighbor.

“The motel. I….I’ll be good.”

Bill smiled, and Sydney was indeed very good. But Bill was not. He never was, as Sydney would learn. But that is another story.

Source: reddit.com/r/sexystories/comments/beawx6/a_stupid_bet_mf_nc_anal_gloryhole