Yes, with a buttplug

Jennifer was alone, naked, in a car that wasn’t hers outside a sex shop her friend had ran into to get a toy for her to play with her own ass with so she could get dressed and stay dressed. Every sound outside sent her into high alert as she tried to not think of being caught in this situation.

Without Jamie there to talk to or distract her all she could think about was her incredible orgasm and that it had came from playing with her ass. The lube leaking out of her still coating her asshole had her tempted to go again and even if it would do nothing about her clothes situation she was still so turned on it seemed worth it. She felt like her whole mind had been rewired by the trials she had faced today.

She adjusted her seating and placed a finger over her slit giving it a quick rub before remembering where she was. She wasn’t really masturbating just absent mindedly grabbing herself. She heard footsteps outside and pushed herself further under the dashboard to hide. Dragging her lube coated asshole against the carpet reminded her why she was naked and why she would be until the curse was sorted out.

Jamie was inside the sex shop and knew she had to be quick but she was looking over the toys to make sure they were comfortable and wouldn’t overwhelm Jennifer. She also knew this stuff might not work and grabbed a few other items for that contingency. She looked at her phone and it already had a text asking where she was from her mom. There was no clothes there other than bdsm gear so she decided that she’d have to shop elsewhere for Jennifer’s clothes.

She made her way back to the car after paying a much higher amount than she expected but figuring that was the price she had to pay for cursing someone.

She knocked on the window only able to see naked legs sticking out from under the dashboard to make sure she didn’t freak Jennifer out by opening the door. Jennifer looked out the window nervously and breathed a sigh of relief.

Jamie stepped in and put down the bag which Jennifer was surprised to see it definitely had multiple items in it. Before she could ask Jamie began to speak.

“Okay, we don’t have a lot of time. Do you know what a buttplug is?”

Jennifer had a basic clue from the name but hadn’t heard of it before.

“I assume it plugs my butt?” She said trying to feel comfortable naked and discussing new butt play with someone she barely knew.

“Yeah, that’s about it.” Said Jamie expecting to have to do a lot more explaining.

Jamie reached into the bag and opened up a small box, pulling out a pink plug that was short, skinny, and made of silicon.

“This is supposed to be the most comfortable one they have. It’s silicone, so it’s flexible and it’s not very big. I know you’re uncomfortable but we need to get this done now.”

She handed the plug to Jennifer and took the bottle of lube out of her bag. Jamie turned her head to give as much privacy as she could given she was also in the car.

Jennifer swallowed looking at the plug in her hand. Jamie was right, it was not that big and it was flexible. It was pink and looked like two small cones with their bases pressed together and then a small flange at the bottom to keep it from getting sucked In. It was as good as it was going to get. She looked up to see Jamie’s turned head and appreciated what privacy she could offer. She coated the plug in lube before spreading her legs and scooting her butt forward. She then rubbed some lube around her anus.

She tried to ignore that she wasn’t alone and that she was afraid but she was afraid. She was afraid it would hurt, she was afraid it wouldn’t work, and she was afraid she would like it, like it even more than her first experience with assplay.

She put her legs up onto the seat and pushed her butt more forward. Jamie saw this out of the corner of her eye and looked accidentally. She saw her friend lining up the plug with her asshole. She saw her asshole was small and pink below her wet lips and felt like she was violating her trust but she couldn’t look away and Jennifer hadn’t noticed as she was too focused on the plug. Her friend’s breasts still looked pert lying flat on her back with stiff nipples and Jamie felt slightly better knowing her friend was likely turned on if not enjoying herself.

Jennifer took a deep breath and pushed the plug against her asshole. She pushed it in and felt her anus expanding as it slid down the cone and she tried to control her breathing and relax. The daylight shining into the car reminded her she could be caught any moment. She got it to the thickest part of the plug and it felt tight and she paused but that only made it worse and wanted to pull it out. Realizing she’d gone this far she pushed a little further and as it shrank down her anus became more comfortable until she got it all the way in and her anus contracted around the base until all that could be seen was the end. It made an embarrassing squelching sound against the lube and she got a full body blush.

“I didn’t...”

“I know.” Said Jamie trying to be reassuring.

Jamie had watched the whole thing out of the side of her eye and she was ashamed to say it made her feel powerful. She had caused all this and despite Jennifer being completely innocent of all she had thought she was it was kind of hot in a dominative sort of way.

Jennifer tried to move her butt around as she had the bizarre feeling of fullness in her rectum and the base pressing against her anus. She felt her clit stiffen as she realized it was turning her on.

“I don’t want to rush you but we need to go.”

“Would you mind if... I masturbated with you here. I mean I still need to cum, right? That wouldn’t be too weird for you? I’m sorry...”

Jennifer felt so weird talking to her friend with a plug up her ass on top of the shame of having to ask if it was okay to masturbate with her in the car.

Jamie put her keys in the ignition.

“We don’t really know. It’s just a theory we’ve been operating on. I would not feel weird at all if you did and I appreciate that you’re showing that much trust in me to do that with me in the car. Don’t be sorry. Do what makes you feel comfortable. I’ll drive to the mall to get some clothes.”

Jennifer closed her eyes and began to rub herself when she was taken out of the moment when she heard a clicking noise and Jamie saying “oh shit.”