An Instagram Nightmare Pt. 03

"Don't ever come to see me again, and don't ever call. You're a fucking loser, and you'd be lucky if Master let you sniff my asshole," her words rang out ruthlessly before she tapped angrily on the screen, ending the call.

I walked over to her and tossed the towel on the couch beside her. She put her phone down and looked up at me, the scowl disappearing from her face. "Well Master, Tight Slit doesn't think he'll be a problem," she told me.

"Turns out he's a more obedient slut than any of us!" She chuckled to herself and then looked back at me. "Is there anything else you want, Master?" she asked.

I nodded my head, "You're gonna take over from Annie, and then I'm gonna take her out for a bit." She looked a little dejected but nodded. "I'd take you too, but you have to work."

I patted her head to reassure her, dropping the towel on the couch beside her. I went back to Annie's room and rummaged through Trudy's toy chest. I found a vibrating dildo and a butt plug.

Then I got the tape from Annie's closet. Taking them back to the living room, I held the toys out to her. Trudy reluctantly took them. "Put them in now," I told her. She gulped.

Trudy hadn't gotten to cleaning up yet, so her slit was still slick. After rubbing the tip of the vibrator against her lips to gather up some cum to use as lube, she gently inserted the vibe into herself. She bit her lip and closed her eyes as she pushed it home, and then shuddered.

She looked at me to see if I had a response for her, but when I didn't she took the plug and moved it to her rear entrance. Her ass rejected it at first, and she had to use a bit of force to push it inside herself. As she got past the big end, it slipped inside her, and she let out a moan.

Next, I grabbed her and lifted her from the couch. I pulled her dress back up to get full access to her crotch and then bent her over the armrest. With her holes both fully exposed, I took the tape and ripped off a big piece. One strip after another, I used the tape to secure the toys inside her.

Once I was done, I gave her one last spank and then lifted her by her hand. "You've got five minutes to clean up, and get ready for work," I told her.

I sat on the couch as she carefully made her way past me to try and get herself presentable for her job. The latex pieces of her outfit came flying back down the hallway as she went, littering the floor.

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Fifteen minutes later, the two of us arrived back in the lobby. Trudy was looking similar to this morning, only now her cheeks were flushed. Her blouse was also unbuttoned at the top. The top three holes.

The shirt hung loosely over her torso, with the collar pulling away to reveal her neckline and the top of her breast. Trudy's perky nipples poked through her shirt while her tiny skirt fluttered as she walked. If she bent over at all, the skirt rode up her ass, revealing two stuffed holes.

Trudy was quick to get behind the desk and immediately started trying to pull Annie from her chair. Annie grabbed her hands and pulled Trudy down across her lap. "So what's the plan, Master?" Annie asked.

"Trudy's taking back over while you and I go shopping. It's time you had a collar around your neck," I replied, giving her a stern look.

She looked a little surprised, and her mouth opened as if to speak, but she closed it moments later without a word. Annie planted her elbow into Trudy's back and placed her chin in her hand.

With her other hand, she started massaging Trudy's ass underneath the skirt. Trudy tried to fight back, but all she could do was uselessly try to grab at her hand. "Do I have to?" she asked quietly.

"Yes, Cock Hole you do," I told her.

She considered it again, "Everyone's gonna think I'm a whore." Her hand found its way down to Trudy's plug, and she started pulling on it gently. Trudy's efforts doubled, and she started kicking her feet.

Still, the difference in size was too great, and she couldn't do anything but rock herself on top of Annie's knees. I moved closer to her and leaned on the desk beside them.

"You are a whore. You sell your body on your live stream every night. You didn't even need me to push you to that," I explained to her. "Now get up and get your lazy cunt moving."

She smiled and then let Trudy go. Trudy slid from her lap onto the floor with a thud. She looked up at Annie angrily but didn't say anything. Annie got to her feet and started walking past me to the door.

I grabbed her arm and stopped her. "Did you think I didn't catch that little bit of defiance?" I asked her. She gave me a sly grin and then nodded her head.

"Bend over slut. If you want to act badly, you're going to get punished," I said, pointing to the desk. I let go of her arm and, she walked over to the front of it. Turning slowly, she planted her hands on top and bent over exposing her pussy and asshole to the front door.

I couldn't help but smile as I walked around her and lifted her cute little pink dress. Her big juicy ass stared at me and enticed me with its supple-tanned skin. I rubbed my hand over both cheeks, massaging them and preparing them. Then I pulled my hand back and let loose a fierce smack that caused her to yelp. "Count it out, slut!" I ordered her.

"One, Thank you Master!" she cried.

I let two more blows ring out, and she started whimpering. Trudy comforted her as Annie spoke, "Two, thank you, Master! Three, thank you, Master!" Her ass turned red after ten more smacks, and her eyes were starting to fill with tears.

Trudy held her face in her hands and continued kissing her forehead while whispering to her. "You're doing great," she said.

I let up for a moment and let Annie enjoy Trudy's presence. I rubbed her reddened skin and watched as goosebumps started to form along it. The breeze must have started to affect her.

I looked around at the empty lobby and out of the door at the front. There was no one around, but that would only be the case for a while. Rearing back a final time, I let out the last two spanks. One on each cheek.

Annie squealed like a pig, "Fourteen, thank you, Master! Fifteen, thank you, Master!" After that, I massaged her ass for a while to rub in the rawness and then pulled her dress back down.

I gave her another minute to recover and then started walking toward the door, keys to my van in hand. I was halfway across the lobby before Annie managed to gather herself and come running along to catch me. She took my hand in both of hers and skipped along beside me while we headed out.

I could swear I saw her turn back and stick her tongue out at Trudy.

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It took us a few minutes to walk to the garage where I had parked, and then another forty minutes or so to cross town. While we drove, I explained the deal I had made with Trudy to Annie.

"You're going soft," she teased. I smiled at her and continued. On the outskirts of the city, there was this skeevy-looking sex shop that I'd never been inside, but it seemed like the perfect place to take a burgeoning exhibitionist.

When we arrived at the run-down strip mall where it was located, the parking lot was pretty much empty. It was sometime in the afternoon so that was to be expected, but the businesses beside it weren't doing well either.

I looked at the store itself, and it even looked like it came from another era. The top had a large neon sign that read "Sex Shop Est. 1953." Clearly a relic that hadn't gone the way of the dodo.

The front window had mannequins in it dressed up in different skimpy outfits. Lingerie, leather, and latex pieces that just barely covered all of a woman's sex. There were also signs listing out some of the products and services they provided. Annie walked past me and pulled open the door. "Coming Master?" she asked, holding it open.

I followed her inside and then looked around again. There was an open area in the middle with an assortment of racks holding different fetish clothing. Bottoms and tops of all different sizes, shapes, and levels of exposure.

Collars and harnesses and all their leather wearables lined shelves nearby. Annie immediately started thumbing through them and picking out a few to try on. To the right side of the shop was a wall of accessories.

They had different models on display, strapped to the little glass platforms that held them. Dildos, plugs, cock rings, basically anything that went in or around your junk was displayed there.

To the left was an assortment of restraints. Cuffs, ropes, tapes, and anything else that could help secure your prey. Along the back wall was a counter with larger, more expensive objects behind it.

Vibrators of every size and strength, bigger toys like sybians, and complex blow-up dolls still in the box. Behind the counter was also the world's skeeviest man. A dude in his late forties with a greasy brown rat tail and grimy-looking skin. He wore a black vest over a green shirt with jeans.

His eyes hungrily stalked Annie as she moved around the store. I smiled at his lack of decorum and walked up to him at the counter. "Like what you see?" I asked him.

"You sir, are a lucky man," He replied, continuing to stare at Annie's ass as she bent over to look at a latex hobble skirt.

"Cock Hole, bend over all the way!" I yelled at her. She looked back at us for a second and then bent at the waist, touching her palms to the floor. Her pussy and asshole were put on full display for the two of us.

I turned back to the shopkeeper, who was now staring wide-eyed at both of her holes while licking his lips. "I need a collar for the fuck toy. Do you guys do inscribing here?" I asked him.

"Ye... Yeah," he muttered, distracted.

"I'll make her suck your dick if you get it done in twenty minutes, " I offered him. He finally turned to look at me, a sparkle in his eye. He looked back at her and then rushed off to grab some supplies from the back.

He returned with a toolbox and set it on the counter. Then he went out into the shop and got a couple of blank leather collars of different widths and brought them back to me.

"Which one you want on her?" He asked, holding up a one-inch collar in his left hand and a four-inch posture collar in the right. I pointed to another one he brought over that was about two inches wide, and he set it aside before putting the others back. "What do you want it to say," he called out while he worked.

"Cock Hole Annie," I replied curtly. Looking over at Annie, I realized she was still standing there bent over, exposing herself. "Annie, get over here!" I yelled at her. She stood up and scuffled over, a timid look on her face as she sidled up next to me.

The shopkeeper placed the collar into a pair of vices that held it in place and then took what looked like a soldiering iron out of the box. He placed the iron onto a wire holder and then plugged it in. He grabbed a booklet from a shelf nearby, and then flipped it open, showing it to me. It was a series of fonts that I could select from. I pointed at a normal-looking Impact font, "And do it in all capitals."

"Cock Hole Annie?" He asked, confirming again. I nodded, and Annie tried to hide behind me. Her face was beet red, and she didn't say a word. He pulled up a stool from nearby and then sat down in front of the vices.

Taking the stencil from the booklet, he placed the letters over the leather, and then with a marker, he etched out the words. Once he was done, he showed it to me, "That good?" I nodded and then reached around behind me to get Annie. I pushed her in front of me and then bent her over the counter.

Reaching down to her pussy, I traced my fingers along her pussy lips. She whimpered and in the glass behind the counter, I could see her close her eyes in the reflection.

Her face looked so innocent and full of embarrassment. The shopkeeper looked over at us and gulped before returning to his work. He took the iron from its holder and started burning the words into the leather.

I pressed my fingers to Annie's entrance and started probing inside. She moaned and her hands flew back to try and slow me down. I grabbed both of them and held them in the small of her back while I worked her to orgasm.

Within a few minutes, she was panting and humping my fingers. Her shame was starting to subside, and her lust was taking over. Beside us, the man was clearly getting distracted because he was letting the iron sizzle in the air while staring at us slack-jawed. "Damn, she's one hell of a freak. You too dog!" he exclaimed.

"Just wait until she's sucking your dick. Then we'll see who the freak is," I said, looking him in the eye. He gulped again and went back to work. My attention returned to the slut.

Annie at this point, had given up all pretenses and was starting to play with her clit. While she rubbed away, her legs were tensing. She was close to cumming, so I added two more fingers.

They drove deep, looking for her G-spot. I must have done something right because she screamed out in ecstasy, and her thighs clamped shut around my hand. When I tried to pull away, her hands clasped around my wrist and held it there.

"Thank you, Master," she said breathlessly. She relaxed on the counter and let go of my hand. Her thighs relaxed and I was able to pull away. I reached my fingers forward to her mouth and she instinctively opened up and started sucking on them.

"Good girl," I told her, patting her ass with my other hand. I turned to look at the shopkeeper who was still finishing his work. "How's it going?" I asked. He ignored me. Pulling my phone out, I checked the time and saw that we were close to the deadline I had set.

Walking around the counter, I went behind him to see how it was and saw that he was actually done. He had decided to add a beautiful-looking diamond into the design beside it.

He was hard at work adding details to it, and shading in certain sections. It looked incredible, so I waited for him to finish. It took him a few minutes longer than expected, but once he was finished, he was excited to show it to me.

"What do you think?" he asked. I took it from him and looked over the handy work. He had a good hand, the lines were perfect, and the diamond he added to the design was quite elegant looking. I showed it to Annie who looked up at it with an exhausted look and nodded.

"It's great, master. Totally what I want to wear every day," she muttered. I smiled and turned back to the man.

"I think you've earned yourself some head, my good sir," I said, waving toward Annie. She looked over at the two of us. It was her turn to gulp and give me a reluctant look. "It's not a debate, Cock Hole," I told her.

The two of us stared into each other's eyes for a bit. Another small battle of wills. She gave up quickly and lifted herself off the counter. Annie crossed around behind it, and then walked past me over to the shopkeeper. He immediately set down the iron, unplugging it, and pushing the holder away from him.

Annie kneeled beside him and unzipped his jeans. It took her a few seconds to fish out his cock, but it came out rock hard. She looked at it with disgust, before looking back at me.

"You better do a good job, " I told her. "You're staying here until he's satisfied."

She sighed and then went to work, taking him into her mouth and licking his shaft while fondling him. He moaned a little as she began, and then his hands went to the back of her head and gently settled there.

I wandered while she sucked, looking around the displays behind the counter at all the expensive toys. The one that caught my eye was an expensive little clit ring. Looking over at them, I saw the shopkeeper leaning back on his stool with his eyes closed. Annie's head bobbed up and down.

This seemed like the kind of place where you could trade favours for products. He certainly wasn't saying no at the moment. "What would Cock Hole have to do, to get you to give us a discount?" I asked as nonchalantly as I could.

He started to speak, "Uh... Well..." It was like his voice was stuck in his throat. He struggled to try and get his bearings for a few more moments, but Annie was trying to torment him. I saw her head dip deep into his crotch, taking him down her throat.

He composed himself, and then eventually he used his grip on Annie's head to stop her. He took a deep breath and then looked over at me. "Well, I could give ya a discount for the blowjob. Hell, she's sucking the soul right out of me, but..., " he trailed off.

"But what?" I asked, taking the bait. He smiled and then pointed to the back of the shop.

"There's a gloryhole back there. You could put her inside, and we could split the money," He explained earnestly. His eyes were lit up at the prospect. Below, Annie was staring back at me with disgust.

"No way, this guy's bad enough," she said quietly. I smirked at her and then looked back at the man who seemed a little disappointed.

"She'll do it, but I want to film her inside the box. That and I want to set her up with a few toys in there," I told him. The light returned to his eyes, and a crooked smile crossed his face.

Annie rolled her eyes and then went back to sucking his dick. It didn't take her long to recapture the shopkeeper's attention and get him moaning. I left them there and started looking through the shop. "Get whatever you need," he called out between moans.

First I went to the back and inspected the "Glory hole" the man mentioned. It was in a small hallway with a glass ticket booth at the front. The booth was empty at the moment but had two signs inside that read "In use" on the front.

Walking past the booth, I saw the hall had two doors on the left and another two on the right. I opened the first door on the left and it was just a small enclosed room. Inside there were four walls, and on one of them, there was a single hole leading into the next room.

It was just big enough for a person to put their head through. I kneeled and looked inside, the hole led into the second room. It was identical to the first room. Going back into the hall, I checked the other side and saw it was the same. Figuring I could force Annie's head through the hole, I went back into the store to find a hood to cover her face.

While I looked through the hood section, I heard the shopkeeper start to groan loudly, and then I heard Annie grunt and gag. Looking over, I saw her stand up and wipe her mouth.

She tried to turn and walk away from the man, but he made sure to spank her one more time before she could get away. She yelped and then scurried out from behind the counter. Annie rushed over to me with a look of desperation on her face. "Can we please just get out of here," she said hastily.

"No, I looked at the backroom, and it's perfect for your next shoot," I said. She looked at me skeptically and then went to have a look for herself. While she was away, I found a pink latex hood with two nostril holes, a mouth hole, and two holes in the back for pigtails.

They had a couple of sizes, so I held a few up to compare. Annie came stomping back, a rush of anger on her face.

"You think I'm gonna stick my head through that and suck some guy's dick with my face out?" she whisper yelled. Standing there in her cute little pink dress and white socks, she looked kind of ridiculous.

Like a real-life Barbie was chastising me. I reached out with the hood in my hand and held it next to her face. Confusion crept into her eyes, and she looked from me to the hood and back. "You want me to wear a hood?" this time the question was a little softer. "For how long?" she added.

"As long I tell you to. Now try it on!" I commanded. Annie took it from me with hesitation and then took a deep breath before sliding the material over her face. She moved it around on her head and pulled her hair through the holes until everything was in place.