“They should certainly renovate this space”, Emily was thinking as she was seated in a booth at the Capital Grille. The decor looked old and the space wasn’t very well lit. She preferred the more open space of Smith and Wollensky on the Seaport but since Capital Grille was his favorite restaurant and they were supposed to go shopping at the Pru, she didn’t mind. Besides, the food was excellent. He had texted her that he would be a little late, because of a last-minute phone call by an important client and to go ahead and be seated. She had ordered a cocktail and couldn’t wait for him to reveal to her what plan he had in mind. She was getting excited thinking about the possibilities when he entered the room, following the hostess.
– Hi Jack, Emily said, how are you?
– Hi Emily, Jack answered. I am great. Sorry for the delay. I had a client I couldn’t not talk to. Sometimes you have to do what you have to do.
– I understand, Emily said. Don’t worry, it wasn’t a problem for me to wait. I actually won a few things on this game I have been playing on my phone. Emily knew that Jack was usually very flexible with his time but that big clients of his law firm needed attention sometimes. Being a very successful lawyer had its downsides.
– So, have you looked at the menu? What are you in the mood for? Jack asked.
Emily and Jack proceeded to have a very enjoyable lunch, catching up on his work as a lawyer and on her classes at the university she was attending. They finally reached dessert and ordered a chocolate cake to share.
– Please bring me a black coffee too, please. Jack said to the waitress. Do you want one too, Emily?
– No thanks, I am good. She replied.
As the waitress was leaving the table, Jack took a small box out of his jacket and put it on the table.
– Don’t open it yet, he said. Take it and go to the bathroom and text me a pic.
Emily blushed. She wasn’t expected that. But she felt an urge to follow his order. She took the box, put her covid-mask on and started walking towards the bathroom. Once in the stall, she opened the box and discovered a small butt plug. She was shocked. She wasn’t sure that she wanted to do this. Yes, they had done some kinky things in the past but this was on a completely new level. And she had never used a butt plug. At least he had taken a really small one. She took it out of the box, turned it around and realized her name was written on the back. She got aroused, thinking he had planned this for a while, had probably ordered it on the internet just for her.
Emily started to push the butt plug into her asshole. It didn’t want to go. She felt very nervous. Is there a special way to do this? She thought. She quickly googled “how to insert a butt plug?” and saw that the most common response was to use lube. Damn, she thought, What do I do now?
Emily looked at the box again and saw a small pouch of lube. She hadn’t paid attention before as she was focused on the plug but, of course, Jack had planned everything.
She opened the pouch and put lube on the tip of the plug. She pushed it into her asshole. The internet had also said to be very relaxed so she thought about something else as she pushed the plug in and, suddenly, she felt it getting sucked into her ass. It was as if it was fitting perfectly in her ass. She stood up and could feel it, but it wasn’t uncomfortable at all. She wiped the lube and was thinking about getting dressed as she remembered Jack had said he wanted a pic. She took her cell phone and took a pic of her ass with the plug barely showing. You could kind of make out the “Emily” tag on it. She texted it to Jack, blushing even though she was by herself.
– Good job, Jack texted back, with a smiling emoji. Now put your panties in the box and bring it back to me.
Emily hasn’t thought of that either but she was decided to follow Jack’s instructions. She wrapped her panties in a ball and put them in the box and went back towards their table. She was wearing a very short dress and thigh-high tights but it was the first time she was without underwear. She could feel the air on her ass and pussy and the butt plug felt awkward as she was crossing the room. She felt as if everyone was watching her and knew she was butt-naked with a butt plug up her ass but she walked with assurance and sit back on her seat.
– Those desserts are really good, Jack said, as he grabbed the box she put back on the table with a shy look. Let’s finish this and we’ll go shopping.
She did enjoy her desert and they were soon on their way to the Pru. Jack was still talking to her about a YouTube video he had watched but she could see in his sparkly eyes that he was very much thinking about the toy she had in her.
As they were going on the escalators, she felt Jack behind her. One of his hands was almost touching her ass and Emily realized he was preventing people from being able to peek under her short skirt.
They walked all the way to the Louboutin store. Jack really enjoyed high heels and she had learned to appreciate them too. She was still working on walking with very high heels and she was definitely getting more comfortable in them. Jack was pointing as different heels and boots that she found really nice and finally settled on the Louise X over-the-knee boots. Emily found them amazing.
– Could we try those in 38 please? Jack asked the salesperson
– Of course Sir, she replied.
Emily really liked those boots. She was hoping they would look great on her. When the salesperson came back with the box, Emily was going to sit down on the couch when she realized she had no underwear on. She felt embarrassed. What if the salesperson saw it. Already the salesperson was opening the box on the floor, kneeling down to take the boots out of the box.
– I am sorry, because of social distancing, I can’t help you with them ,the salesperson said.
– Of course, Jack replied. I will help. Jack kneeled down and took a boot as Emily was sitting down. He presented it to her and helped her slide her foot and leg in. Emily felt aroused. Now it was Jack facing her. Could he see her bare pussy? He wasn’t showing any indication he could. She felt drawn to open her legs more, flashing him. Jack looked at her as he was handling her the second boot and she could guess he was smiling, despite his covid mask. She blushed. Lucky for those masks, she thought to herself.
Emily zipped the boots on and got up. She walked to the mirror. She looked so good in them. She loved them right away. Because she is petite, the 100mm heels were really giving her a boost, and she felt more confident in them. She walked a little and although the high heels made her a little uncomfortable, it wasn’t so bad. The heels made her ass higher and she could feel the butt plug more. She had almost forgotten about it, as it felt more and more part of her as time as passed. But the heels made her feel more conscious about it. What if they could all tell she had it in her?
Jack was very complimentary.
– You look amazing Emily. Those definitely fit you.
– Yes, you’re right. I was a little worried about my calves not fitting at first but it’s not a problem at all, Emily replied.
– We’re taking them, Jack said to the salesperson. Actually she will wear them now.
– Of course Sir, she replied and they left the store with Emily’s shoes in the box and Emily wearing her new boots.
– Let’s go to Dior, Jack said.
– Oh yes please, Emily replied. It was her favorite store so she was excited about it, even though she was walking towards it relatively slowly. She didn’t want any accident with the high-heel boots that would expose her.
At the Dior store, Emily had so many items that attracted her that she didn’t know what to look at. But Jack took his phone out and showed something to the salesperson.
– Yes we do have it Sir, she said. Please give me a second.
The salesperson went looking in another part of the store and came back with a plate with different necklaces on. Once she was closer to them, Emily could see that those were chokers. They did look very pretty.
– What do you think about this one? Jack asked Emily as he took one of the plate.
– Yes, I was looking at this one too, Emily answered.
– Let’s try it, Jack said.
Emily turned around and Jack put the choker around her neck. It looked so good on her, she thought. And it would remind her that she belonged to him, that she was his toy.
As she was thinking about it, the choker slipped off her hands to the floor. She was stunned.
– Get it, Jack said to her in a quiet but stern voice.
She bent down to grab it. She could feel her skirt lifting up in the back, revealing her bare ass. She felt his pants touch her and his bulge rubbing against her. She was so aroused. She was so close to being exposed, standing with her bare ass with a butt plug in it.
But she acted like nothing had happened and grabbed the choker.
– We’re getting it, Jack said to the salesperson, as he secured it back on her neck.
They left the Dior store.
– Where are we going now Jack? Emily asked.
– The Gucci store is right here, he replied.
– Oh yes! Emily replied excitedly. She was really getting spoiled today.
They entered the Gucci store and she started browsing around.
After a while, Jack made a sign to join him near the fitting rooms. She walked there and was surprised when he handed her a lingerie set.
– I think you need panties and a matching bra, Jack told her.
– I’ll let you change in this room Miss, the salesperson said. You can try it on top of your underwear.
Emily entered the fitting room and she could feel she was blushing. She didn’t have underwear on.
– Keep the boots, Jack whispered to her, waiting outside the door.
It was difficult to put the panties on with the boots but Emily managed. It was fitting well. It was such a sexy and comfortable set.
Emily opened the door and Jack sneaked in. Emily looked amazing. Her fit and toned body was so hot. Her perky tits were so enticing and that lingerie set looked even better with her boots on. Her head was looking down as she felt ashamed of being almost naked in front of him.
– Turn around, Jack told her.
Emily executed, turning around to show her ass.
– Bent over.
Once again, she followed his order. She felt so aroused, knowing that he was looking at her ass with the butt plug showing.
– Do you like wearing a plug? Jack asked.
– Yes I do, she answered sheepishly.
– Good girl. You’ve been so obedient today, you’ve made me very happy.
– I love pleasing you.
– Good. Let’s see if you still do.
Emily didn’t know what he meant but she suddenly felt his hand on her ass. He started spanking her. It became so hot. Feeling his hand on her, punishing her. It felt so good. But what if the salesperson heard. It was both scary and exciting.
Spank, spank, spank! Three short but hard hits sent her ass on fire. She almost shouted but caught herself.
She can’t. She can’t say anything. She has to take it silently she thought. He can do whatever he wants with her and she’ll have to take it. That thought started to make her pussy wet. She would be such a good girl. So submissive, always obedient to him. She could feel his hands all over her ass, calming down the pain.
– Sit down on that couch, he said.
She did, facing him. He pushed her backward and kneeled down in front of her. He pushed the panties on the side of her pussy and started licking it. She could feel his tongue all over her pussy. It felt so good. Her pulse was accelerating as she felt her clit going on fire. He was sucking on it, biting is gently. She wanted to moan so bad, she had to bite the inside of her mouth not too. What if someone came in, she was completely at their mercy. She could feel the blood rushing to her clit. She wanted to moan so badly. She felt his hand reach her tits and squeeze them. Her nipples were so hard. He was squeezing them so hard, and yet it felt so good. Suddenly she felt his tongue inside her pussy. It was reaching so deep. The motion of his tongue on her pussy and his fingers pinching her nipples was so intense. She was completely exposed. She was rocking her body back and forth, she wanted more of his tongue inside her. The butt plug felt so good. It was the first time she had felt that anal pleasure. She felt it deep inside. It was so intense to have both the anal plug and his tongue going deep inside. Suddenly he bit her clit a little stronger and she came. She felt such a strong wave of pleasure in her ass and pussy. She felt her juice coming out. “Oh no, oh no” she thought, It’s going to be all over.
Jack was waiting for it. He loved the way she came. Such strong orgasms that were rocking all of her body. She always had a thick juice coming out of her that he couldn’t get enough of. He swallowed it all, tasting that sweet nectar.
As she was coming back to her senses, Jack told her to put her clothes back on. The GUCCI panties were all soaked with her juice. Her thighs were covered with it. She did look presentable with her clothes back on and he opened the door.
Jack found the salesperson.
– We’re taking the lingerie set, Miss. She’ll be wearing it right now actually. Here is the tag.
The salesperson was a little bit taken aback but she proceeded to the register.
Emily felt so good. Sure, it was a little awkward to walk in the high-heel boots with the butt plug still in her and a soaked underwear. But she felt so fulfilled, to be his toy. She couldn’t have asked for more.
– She said to wash it by hands only, Jack told her with a smile as they were leaving the store.
– Yes I will, Emily replied, as her mask couldn’t completely hide her whole face blushing.