Gracie's Three Punishments Ch. 04

Quickly she stood up, as Gracie had, and pulled down her gym shorts and panties revealing her bare lips and a dark landing strip atop her mound. She sat back down, but unlike AJ and Gracie she was still cross legged, happy to show her symmetrical, pink labia to her friends. Of the three, Kelsey was the only one with the "perfect" symmetrical lips that were ubiquitous online. Gracie wasn't jealous of Kelsey, but she wished she could be as confident.

"That gets easier every time," AJ said.

"Yeah a lot better than the first time in front of a guard," Kelsey added.

"That was your first time?" Gracie asked, she knew it had been AJ's but thought Kelsey might have been more experienced.

"Kind of, it was the first time exposed in a bright room. I'd hooked up with guys, but it was always dark and under the covers," she laughed nervously.

"That makes sense," Gracie told her, "Having a male guard sucks, too."

Kelsey nodded.

AJ chimed in, "I've still never had a man touch me."

"The guy in the tent," Kelsey reminded her.

"Right, I forgot about him. Still, not, you know, down there," AJ responded.

"We don't have to talk about that day," Gracie offered, "How do you suggest I do this, Kelsey? You're the expert."

"As much lube as you think you need and relaxation. I used my finger first and built up. At first I did it in the shower but then I started doing it in the mirror in my room so I would know what it looked like."

"I don't really care how it looks. Tomorrow is private, anyway. I'll just do it on the bed, it won't be that bad, not my sheets anyway," she joked.

"You don't have to go first," Kelsey said, "I've done it before."

"No, I'll go first," AJ volunteered, "I never got spanked last week, I owe you."

"I'm not going to stop you, but there is no owing going on here," Gracie protested.

"Whatever, you know what I mean," AJ said, "Pass the lube over, Kels."

"Alright," Kelsey grabbed the lube and passed it to AJ.

AJ laid on her right side, so her head pointed toward Kelsey and her ass pointed away from the circle. She supported her head with her right hand and her left hand reached behind her toward her cheeks.

She had chosen a position where the other girls couldn't see what she was doing, which was fine as far as Gracie was concerned. She didn't need to watch this, but she was touched that they were willing to share in this with her. "Maybe they're getting something out of this."

AJ's hand was rubbing back and forth. After a few seconds, she reached for the lube letting her head drop so she had two hands to fiddle with the lid and squirted a large helping of lube onto her index finger, "Wow that was more slippery than I was imagining."

"They make it like that for a reason," Kelsey said, "You'll be fine, just go slow."

"I've had a finger in my ass before," AJ reminded her, referencing the cavity search they had all endured. She reached back toward her ass and brought her left knee forward. Gracie watched as she took a deep breath and frowned as she pushed her finger into herself. After a moment she smiled to her friends, "See? No big deal with the lube."

"You don't have to use the brush," Gracie told her.

"No, no, I'm going to try at least." AJ rolled more onto her stomach, pressing her breasts on the comforter, and propped herself slightly on her knees so her ass pointed upward off the bed, "Will you lube the brush, Kels?"

Kelsey grabbed a black handled brush off the bed and squeezed a line of lube onto the handle. She rubbed the lube all around the handle and handed it to her girlfriend. Gracie looked down at the lime green brush next to her. It was maybe eight inches long, half of it the round handle that tapered at the end and where it connected to the flat backed brush. At its widest point in the middle it was less than an inch in diameter. Gracie realized it was probably just about perfect for its purpose tonight, Kelsey knew what she was doing.

AJ held it by the bristle end and reached behind her. With her other hand, she spread her cheeks and, closing her eyes, she started to push the handle into her. She gasped softly but kept pushing it in. It didn't take her long for her to get it all the way into her.

Gracie was impressed. AJ even left it there and returned her hands to the bed though she was breathing heavier than she had before. The figure she cut was strange. The pretty blonde teenager was on her knees and elbows with her ass in the air with the bristle side of the brush sticking out like a tail.

She thought it wasn't the most realistic prediction of the position she would be in tomorrow. Sure, it would give the technicians access, but she thought being strapped into a gynecological chair, like she had been last week for her spanking, was more likely. That option just seemed simpler for all involved.

"Are you ok?" Kelsey asked.

"Yeah, it's fine. It's ok once it's in. It didn't hurt too much. I'm going to take it out now, though."

She reached back and grunted as she pulled the brush out of her hole. Quickly, she got off the bed and walked to the bathroom. Gracie heard water running and soon AJ returned without the brush, "No reason to have that on the bed."

Gracie could tell AJ was flustered but was trying to hide it.

Kelsey rubbed her friend's hand, "Good job, much better than my first time. I actually don't mind the feeling once it's in, as long as the thing isn't too big."

"Yeah, the feeling of it coming out was . . . something," AJ declared.

"You like it?" Kelsey asked, sounding surprised.

"Like I said," AJ responded, her hand moving slightly toward her crotch, "It was something."

"I can leave you girls alone," Gracie offered.

"No, I mean, maybe later," Kelsey said, winking at AJ.

"Yeah, something for us to look forward to," AJ said quickly.

Gracie wasn't sure what that meant. "Are they expecting a threesome?" She decided that wasn't going to happen, but they could do whatever they wanted.

"I think you're next, Kelsey," AJ prompted.

Gracie wasn't going to complain about going last. She had never liked anal with any of her old boyfriends, but she was going to make herself do this. The practice had helped last week and there was a lot of peer pressure, now that AJ had done it.

Kelsey frowned as she rubbed lube on the handle of a dark blue hairbrush. "For somebody who planned these nights, she never seems that excited to participate," Gracie thought, "I guess that makes her a good friend, though."

"Don't make fun of me," Kelsey requested, "But this is the best way to do it."

She got up from her cross-legged position and sat up on her toes. She spread her knees far apart exposing her lips to her friends even more than she had been before.

"Wow," AJ complemented.

"Not now," Kelsey responded. She clearly wasn't looking forward to her routine, but she caught herself, winking at her girlfriend.

Holding the brush in her right and using her left to support herself, she positioned the brush underneath her. She hesitated, taking some deep breaths, before slowly lowering herself onto the handle. She winced as the handle started to disappear inside of her. She supported the brush with her hand but didn't push it up into her, instead she gently moved her ass side to side, sliding the handle into her hole.

Ten seconds later, it was in her all the way up to the hilt and she exhaled, "There, done." She slowly closed her legs and let herself fall down on her side, so the brush pointed to the side away from AJ.

AJ petted her friend's hair, "Good job, sorry to ogle."

"It's ok," she turned her head to Gracie, "It gets better the longer you get used to it. Eventually you can just ignore it."

"You don't have to keep it in," Gracie told her, "I can tell you don't like it."

"It's not the brush, it just brings up some memories."

"Let me take it out then," AJ offered.

"Ok, I trust you."

AJ scooted over toward Kelsey and reached over her. Slowly, at first, she wiggled the brush free, before extracting it quickly once the widest point was out. Kelsey gasped as it was removed and laid her head in AJ's lap.

AJ was left holding the hairbrush, but Gracie could tell she didn't know what to do with it. Wanting to let Kelsey stay with AJ, she got up and motioned that she would take the brush to the bathroom. AJ handed it over and went back to stroking her friend's hair as she recovered.

Gracie went to the bathroom feeling guilty for what she'd just put Kelsey through. "If I feel peer pressure, she must feel it too, and she has worse memories."

She washed the handle of the brush with soap and water and laid it on a towel next to the brush that AJ had already cleaned. "Maybe I should call this off, that wasn't easy for Kelsey," she debated with herself as she took her time washing her hands.

As she was about to leave the bathroom, she checked herself. Reaching a hand between her legs, she touched slight dampness. "Damn, this whole routine is getting to me." Everything she had been doing with her friends was so intimate even if they never touched each other. She really wasn't surprised when she thought about it. "Oh well, I know they'll get over it."

She walked out of the bathroom, prepared to offer an end to the night. However, it was clear that the girls weren't ready to quit. AJ was sitting with her legs crossed and Kelsey was straddling her girlfriend, their lips locked together. Both of them flushed as they saw Gracie return. They quickly separated and Kelsey climbed off AJ's lap as Gracie sat back on her bed.

"Sorry," Kelsey said, flustered.

"It's ok, I can leave you guys alone. We don't have to keep going. I'll go take a long shower."

"No, no, you don't have to. We can keep going. I mean, you don't have to," Kelsey blurted, "Wait, let me catch my breath."

Gracie didn't know what she wanted to do. She would have felt bad to quit after watching them, but she also felt bad about interrupting whatever their time together.

After collecting herself, Kelsey continued, "It's whatever you want to do. We'd be selfish to run you off because we're horny." AJ nodded in agreement.

Gracie decided to just be honest with them, "Girls, I'm turned on and I'm not sure what I want to do. I could just take care of myself in the shower and give you guys time out here, but I feel bad not, um, practicing after what you guys did."

"Do both then," Kelsey suggested, "We can be patient, we would feel bad if you didn't get to practice because of us."

"I guess," Gracie started, but Kelsey wasn't done yet.

"You can join us if you want. We both agreed before tonight."

Gracie thought that might be what they were aiming for and she couldn't deny it was tempting. "I don't know, girls," she said, giving herself time to think.

"Whatever, you're comfortable with, but we both have a crush on you," AJ assured her, smiling.

"Does that make it weirder?" Gracie thought. She debated with herself, "Am I leading them on? Is this irresponsible? Am I asking too much of them?" She shook herself out of indecision, "No, they're adults and this was their idea. It will be ok."

Gracie finally picked a middle ground, "I'll take care of myself on my own bed. Is that ok?"

The two younger girls looked at each other and nodded. Kelsey spoke, "That sounds good to us. We know you like being watched now." The girls laughed, putting Gracie at ease.

She couldn't deny that. Her heartrate was quickening now that she knew what was going on. "This was probably always going to happen. It'll be fun."

Gracie grasped the lime green brush next to her and held it up, "I guess I have to do my practice, don't I?"

"If you think it will help," Kelsey responded.

"Last week did, and I can't back out after you guys. Toss the lube."

In a moment, the bottle landed to her side. She debated how she should sit. AJ's method seemed strange and not helpful for tomorrow, while following Kelsey's lead scared her. What if she toppled over? Finally, she decided to imitate a gyno chair the best that she could since it seemed the most likely position the next day. She put her feet on the floor and slid her butt forward so that it was on the very edge of the bed.

With some reluctance, not from showing her friends her vagina but from the fear of how wet it was, she opened her legs revealing her dark labia to the room. Below her cleft, partially hidden by her cheeks, her dark bottom hole awaited her fingers and soon the brush handle.

Gracie looked at her friends, whose eyes were transfixed on her privates, and a shiver went through her. "Yep, I like being watched. That's probably good for tomorrow, makes it easier."

Her right hand slid down from her stomach, over her mound, and, brushing quickly over her lips, one finger found her anus. She pushed against it and, as she expected, she couldn't get far. "Relaxation and lube, like Kelsey said," she reminded herself.

She took some deep breaths and fumbled with the lid of the lube bottle. She was nervous and shaking, not from fear, she realized, but from anticipation. Finally, she got it open and squeezed a few drops onto her finger. "Relax, I've had fingers in my ass before."

When her finger reached her ass, she didn't hesitate, figuring the guards wouldn't tomorrow. She pressed her finger against her hole, and it relented. Quickly the first two knuckles of her finger were in her ass. She wiggled it around, testing how it felt and trying to prepare herself for the brush. It hurt slightly, but at least it was her own finger. After a few moments she brought it partially out before pressing it back in, training herself to not bear down.

After she was satisfied with her warmup, she pulled her finger out. Still quivering from anticipation Gracie dribbled lubrication onto the gel handle of the brush and twisted her hand around the grip, spreading the wetness all over it. She flipped the brush and held it by its head, the bristles were cheap plastic and spread to the side as she gripped it. She reached down and positioned the handle before her hole and started to push it in.

As soon as the handle started to widen, Gracie felt uncomfortably full. She wavered, looking at her friends who were giving her supportive smiles. "Come on can't quit now. They didn't."

Gracie restarted, pulling the brush out a little. Now she rotated it back and forth as it slid in. She was better lubricated now that some had been deposited inside her and quickly it was all the way in. She released the head and felt her muscles contract around the insert, involuntarily trying to expel the object.

She closed her eyes and imagined what it would be like tomorrow at the Punishment Center. In her mind's eye, Gracie was strapped down in the same position as last week. A masked punishment technician was hovering over her as he inserted probes between her legs. Surprised, Gracie realized she wasn't that scared. She had gone through so much the last few weeks that she knew she could get through whatever happened tomorrow.

Opening her eyes, she saw her friends still watching her and arousal surged between her legs. She pulled the brush out from her ass and sat up. "That wasn't bad. I think I'm ready."

Kelsey and AJ smiled as Gracie walked to the bathroom. Gracie washed the brush and her hands and checked between her folds. She was still wet. Her mind was a jumble. She couldn't put her finger on what exactly was turning her on and she ran through the options, "Intimate night with friends, being watched, or am I looking forward to tomorrow?" The last choice worried her, but maybe she could use the feeling. If she could make herself look forward to being seen naked by the guards and techs, then it was better than being scared.

She looked at herself in the mirror, "What has happened to me?" Two weeks ago, at her first punishment, public nudity was what worried her the most, but now she thought she could use it to distract herself from the real punishment. Finally, she shook her head, "Whatever. I'll do whatever I can to get through this. Less than twenty-four hours and I'll be done."

Gracie returned to the bedroom expecting the girls to be all over each other and they didn't disappoint. Kelsey was laying on top of her girlfriend. Their lips were locked together, and they were grinding into each other. She tried not to watch them too intently. Gracie didn't get off on voyeurism. "I wonder if they like watching me or if they just can't keep their hands off each other?"

She laid back on her bed and decided to focus on herself. She propped up some pillows so she could lean back against the wall and spread her legs. Well-practiced fingers quickly split her labia and started rubbing slow circles around her clit.

Gracie closed her eyes and she was back in the theatre where her pussy was spanked last week. Her legs were tied up and spread for the crowd to enjoy. She couldn't remember any specific faces from that day, so her fantasy was populated by old friends, acquaintances, and coworkers who were staring at her bare lips and applauding.

Gracie's finger started rubbing harder around her clit as she relived her exposure and the crowd's adoration. She reached her spare hand across her chest and started to roll her nipple between her thumb and forefinger. She squirmed under her own touch, lifting her hips and grinding into an invisible partner.

As she started to gasp involuntarily, Gracie was suddenly self-conscious and turned her head to look at her friends. Both panting, they were obviously in their own world. They had rolled onto their sides, with their backs toward Gracie. Kelsey was the big spoon and her hand was reaching between AJ's thighs.

Gracie pulled her eyes from her friends and returned to her own fantasy. She realized her hands weren't tied to the chair and she couldn't help but rub between her legs. She was masturbating for the crowd, running her fingers from her clit to her opening. She felt herself approaching the finish as she imagined an ex-coworker's face light up as she spread her lips for the crowd, giving them an unfettered view.

Back in reality, she slipped her finger into her soaked hole and pulled wetness up to her clit as she rolled over into her favorite position. Her nipples rubbed against the comforter as she ground her clit into her palm and her fingers dipped into her cunt. She looked at the bed next to her, where Kelsey's hand still played between AJ's legs, and listened as AJ moaned, overwhelmed by her girlfriend's work.

Returning to her imagination, the masked guard loomed over her. He reached between her legs, but this time he delivered pleasure, not pain, as his fingers slipped into her hole. Soon Gracie climaxed and she moaned, matching the teenager's exclamations. As Gracie came down her fantasy dissipated taking all her worries and expectations for the next day with it.

Exhausted, Gracie pulled down the sheets and climbed into the bed. The girls had switched positions. Kelsey was arching her back as AJ went down on her. Giving them privacy, Gracie rolled over. She listened as the sounds of Kelsey's passion were the last thing she heard before falling asleep.