Girls' Night Out Ch. 12

"Ok I guess I guess we have some dinner dates."

Kylie took a sip of her wine. "My turn," she began. "It was the best Thanksgiving I had in a long time. I consider you guys my second family but this was my real family. Suzi's home is amazing and it was beautifully decorated. My two nieces are just so adorable. Little Katie and I became friends for life." She hopped off the bed and retrieved a piece of paper. "Here this is picture of Katie and me." She handed it to Angie.

"What beautiful eyes you have!" She laughed as she handed it to Cassie.

Cassie looked at it and smiled. "Excuse me but what are these suppose to be?"

Kylie took the paper back. "Don't you know? They're my boobies!"

The girls started to laugh.

"She didn't call them that?" Angie managed to ask.

Kylie nodded. "Oh yes she did. Right in front of her mother and father and sister too."

"Wow, that's too funny!" Cassie said.

"Yes it was but I don't think her mother thought so," Kylie replied. "Jack's parents, John and Maggie, were just great. I think I may have the grandfather I never had."

Angie reached over and squeezed Kylie's hand.

"Any way Cassie you right. Jack's younger brother was a horn dog. He kept trying to hit on me but I couldn't even give him points for trying. Jack's sister and her family, let's just so they were interesting."

"What do you mean?" Angie asked, setting her glass down.

"Let's just say they don't put the fun in dysfunctional. Her husband was just as bad as Jack's younger brother. He tried to corner me in the kitchen once. I don't think I made a good impression on the sister either."

"You?"

"Yup. It seems her daughter Chrissie is a little troubled. She confused about college, about boys and her mother doesn't give her a break on any thing. So when we went shopping she and I got separated. We talked and I took her shopping, you know girl stuff."

Angie smiled. "Let me guess, Victoria's Secret right?"

"That was one of the stops. Chrissie said she had never been there so.... We went."

"And that went over, how?" Angie asked.

"Like a lead balloon, but." Kylie took out her phone. "Look at this text." She showed them Chrissie's text.

"Nice," Cassie said, " A black thong, huh?"

Kylie grabbed the phone back. There was a video of Chrissie spinning around, modeling her panties. "Oh boy, didn't see that before. Looks like it was taken by a friend."

Angie leaned over. "Yeah, either in the girls' locker room or bathroom."

"I better text her back and say no more pictures. Maybe she should delete it. I don't trust her mom not to find out."

Cassie nodded. "Good idea."

"Why does she think she is confused about boys? Does she think she gay?" Angie asked.

Kylie sighed. "Her mom is pressuring her to have a boyfriend and she told me she wasn't really interested. I told her about our situation, about the three of us living together. She seemed genuinely intrigued about it."

"What you tell her about you?" Cassie asked.

"I told her the truth. I said I like girls. I said Angie was bi- and I said you weren't sure yet. Was that ok, Cassie?"

Cassie frowned and then said, "I guess so."

"I gave her my number so she could text me or talk. It seemed like the thing to do."

Angie leaned over and gave Kylie a hug. "You are such a good person."

Kylie hugged her back. "Thanks. Now let's talk about plans for Christmas."

Cassie said that her sister was having it at her house this year and that's where she was going. She said that Angie and Kylie could come if they wanted. Angie stated her Mom and Dad were going to Florida for Christmas. Her sister had a new baby and that's why she wasn't up at Thanksgiving. Her parents hadn't seen the baby so that's why it was Florida for Christmas. She was thinking about flying down herself.

Kylie stated her plans. "I plan on going to my sister's in New Hampshire. Since Christmas is on a Sunday, I thought I go up Friday evening and stay until Monday. Angie, it might be an opportunity for you to meet them if you would like. Think it over."

Angie could tell by the look in Kylie's eyes and her tone, she wanted Angie to say yes.

"Ok, there's another thing," Angie brought up. "We usually do a Girls' Night Out before Christmas. We go over to Springfield, shop, and see the Festival of Lights. It seems a little more difficult this year, not counting Covid, of course. Alexa and I have been talking and trying to set a date. Nothing yet. It seems everyone is busy. Any ideas?"

"Well my dad's birthday is coming up. Can't miss that," Cassie said. "Hey maybe you could come for that? Just saying."

"No plans that I know of," Kylie added.

"I'll talk to Alexa again. Now one more thing." Angie hopped off the bed as the two girls looked at each other. She returned with two small wrapped packages. She gave them the girls. "For you," she said.

Cassie and Kylie quickly unwrapped them.

"What are these?" Kylie asked, raising an eyebrow.

Angie laughed. "They are matching butt plugs. Yours is pink, Cassie's blue. This is to celebrate you both losing your anal virginity!"

Cassie looked over at Kylie. There were questions in her eyes.

Kylie opened the box and held it. Suddenly it began to vibrate. "What the fuck, Angie?"

"Yup, multi speeds. Just push the button on the base," Angie said with a glint in her eyes. "Ok here's the challenge. Let's see who can wear it the longest without removing it. One who can will get a reward. The one who can't, well."

Ever since she had known Angie it was her who pushed the envelope. It was Angie who came up with the idea dressing as a girl, getting Kylie to take some chances with clothing and of course taking Kylie's anal virginity. This was not too far a reach for her.

"You mean put this in me and go out?" Cassie asked.

"Sure, just for tomorrow, one day. What do you say?" Angie asked with a smile.

Cassie looked at Kylie. "I will if Kylie will."

"Ok," Kylie replied. "What's the harm?"

***

Tuesday

"Assume the position, sweetie," Angie said as Kylie knelt on the bed. Kylie placed her head on the pillow and raised her ass in the air. "I'm going to lube you up pretty good." Angie looked at Cassie. "First Kylie, then you."

Angie looked at Kylie's cute little asshole. She had an urge to run her tongue around it but decided now was not the time. She smeared some lube around it and then placed two well lubricated fingers at the opening.

Kylie complained, "Its cold."

"Sorry. I'll remember that for Cassie."

Angie rubbed the two fingers over Kylie's ass hole before slowly slipping them inside.

Kylie gave an involuntary moan as Angie's fingers entered. It felt so good.

Seeing Kylie's reaction, Angie took her time. She slowly moved in and out. On the in stroke, she buried her fingers deep and then wiggled them. Again Kylie moaned.

It was doing more than causing her to moan. A drop of pre-cum appeared at the tip of her cock as Angie's fingers probe her butt. Her cock began to harden.

Angie glanced over at Cassie who seemed mesmerized by what was going on. Cassie licked her lips as she watched.

Angie removed her fingers. "Time for the plug, sweetie. It might seem a bit big. I'll go slow."

True to her word, Angie did go slowly. It only increased the pleasure Kylie was feeling. Tiny moans came from her until Angie pushed it all the way in it. Kylie's ass gripped it tightly.

"How does it feel?"

Kylie sighed. "Full but good."

"And how about this?" Angie asked as she pushed the button on the base and the plug began to vibrate.

"Oh fuck, babe! Too good, shut it off."

Angie leaned back. "No you do it. Just push the button."

Kylie reached behind her but found it difficult to reach it. The vibrations continued. She became more determined to shut it off. Finally she reached and pushed the button. Expecting it to stop, it instead changed intensity. "How do I stop it?" she yelled.

"I told you it had variable speeds. Just press the button and hold it, it will stop."

Kylie did as she was told and the vibrations stopped. She rolled onto her back, her hard cock standing upright and proud. "I don't know if I can do this."

"Giving up already? I'm surprised. Besides now Cassie knows how it works." Angie turned to Cassie. "Ready?"

"Ready?" Cassie thought. She was more than ready. Her pussy grew wet watching all this and she was sure some wetness had flowed down her ass crack. She quickly assumed the position.

Angie smiled as she found Cassie's ass already wet in anticipation. Instead of teasing her like she did Kylie, Angie lubed her up, inside and out, and then inserted the plug. She turned it so Cassie could feel the sensations.

Cassie was sure if she let this little baby continue to vibrate she could cum all over it. Instead she easily reached behind her and shut it off. She could wait.

Kylie suddenly remembered her meeting with Mr. Fairchild. She quickly got dressed, white blouse and grey skirt, black stockings and heels, and a black jacket. "How do I look?" she asked the girls.

She kept herself busy, tidying the office and rearranging the decorations. So much so she forgot the plug in her ass. Only when she sat down did she feel it. Instead she kept moving. She wasn't sure just what kind of business Mr. Fairchild was interested in but she was going to be ready. She had some water and small Coke bottles in the refrigerator just in case he wanted something.

Promptly at 11, a black Porsche pulled into the lot. Kylie checked herself in the mirror and went out to greet Mr. Fairchild.

What she saw was a tall, distinguish looking older man. His grey hair was sprinkled with black hair and the same could be said for his neatly trimmed moustache. He looked to be a little over 50. He stood about six feet tall and dressed in a grey flannel suit, he walked with an air of someone who do knew what they were all about.

He walked to the other side of the car and out stepped an absolutely stunning blonde. She was drop dead gorgeous. Long blonde hair, blue eyes, long legs and an amazing figure that was shown off superbly by tight mid-thigh black dress, this woman was by far the most beautiful creature Kylie had ever seen. Together they walked to the door.

"Good morning, Mr. Fairchild," Kylie greeted him. "Welcome to my gallery. Won't you please come and follow me." Kylie escorted them to the office. "Please be seated. May I take your coat, miss?"

"Jonsson, Ingrid Jonsson."

"Please make yourself comfortable, Mr. Fairchild, Miss Jonsson. Would you like anything to drink? Water?" Kylie hung up Miss Jonsson's coat and sat down behind the desk. "Now what can I do for you?"

"I will come right to the point, Miss Stevenson," Fairchild began. "I own a number of galleries, one here on the Cape and others further up the coast. They are fairly successful. Now I heard about your gallery. It seems you have turned this into something that is becoming well known. Actually taking some business away from my Provincetown gallery, taking some of my clients and buyers."

"Sure, Mr. Fairchild, you must not believe that was my purpose." Kylie leaned forward to the edge of her chair. "I was just hoping to get my business going." As she moved in her seat, she felt a strange sensation in her butt. "Oh God! No!" she thought. By shifting her seat she accidently pushed the button on the plug. It began to vibrate!

Her first thought was 'Can they hear it?' From their reactions, the answer was no. Her second thought was 'How can she shut it off?" Her third thought was "Damn, it feels so good!"

"So, Miss Stevenson, what do you think?" Kylie heard Fairchild ask.

She tried to refocus. "Excuse me, Mr. Fairchild would mind repeating that?"

"Yes, Miss Stevenson," he began again. "I would like to buy your gallery."

"I see," Kylie said sitting back in her chair. This slight movement caused the plug to change rhythm. It began to pulse. Kylie moaned quietly.

"What, Miss Stevenson?'

She was finding it hard to sit still. She squirmed in her seat and she felt herself growing flush. Her nipples began to press against blouse. Her cock developed a mind of its own and began to harden and grow. She had to get out of there. "Excuse me, sir. I won't be a moment." She stood and walked quickly out of the room.

She could hardly walk as she hurried down the stairs to the studio. There she went into the bathroom. Luckily today she wore stockings with a garter belt so all she had to do was lower her panties. She reached frantically for the button. Pushing it caused the vibrations to stop. She gripped the plug, slowly but gently removed it. She gave a long sigh as she did.

Having done that she looked down at her cock. It was rock hard and covered with pre-cum. The front of her panties were also soaked. She checked the front of her skirt to see if was leaked on it. It was dry.

"Well this isn't going away soon," she thought. "Just have to tuck it away and hope for the best."

Kylie straightened herself and returned to the office. She found Mr. Fairchild was gone. "Excuse me, Miss Jonsson, I'm sorry about that."

"That's alright. He had to make a quick phone call. Please call me Ingrid. I hate formalities."

"Well Ingrid, my name is Kylie. Do you mind if I ask you a question? What do you do for Mr. Fairchild?"

"I am what you call his girl Friday. I do a little of everything for him, secretary, accountant, associate. If you decide to work for him, you will be paid well with great perks and benefits."

"Work for him? All I thought he wanted to was buy the gallery," Kylie asked.

"No, Kylie. He wants you to manage the galleries on the Cape, here and in Provincetown plus another small shop there."

Kylie smiled. She realized she really lost focus for more than a few seconds.

Fairchild returned to the office. "Is everything all right? You looked a little flushed there. Did you and Ingrid talk?"

"Yes we did, Mr. Fairchild and I must say I am quite flattered by your offer. As long as I understand this, you are offering to buy this gallery and offering me a job? Correct?"

"Yes, that is correct, Miss Stevenson."

"Can I have to after the holidays to think about it? I need to talk it over with some people."

"Miss Stevenson, take as long as you want." Ingrid and he stood up. "Here is my card. Call that number when you made up your mind. We can talk numbers then." He turned and headed out the door.

Ingrid lingered behind for a moment. "This is my card, Kylie." She flipped it over and wrote something on the back. "This is my personal number. Call any time you want to talk or get together." She gave Kylie a knowing smile.

As the Porsche drove off Kylie pondered her options. Either way it was a big decision.

***

Tuesday Night

Kylie was extremely angry with both Angie and Cassie. "That little stunt almost caused me some big trouble!"

Angie, in all seriousness, asked, "Why, what happened?"

"At first," Kylie began to explain, "The plug felt kind of good, little filled feeling but good. I went about doing what I had to do. At 11, Mr. Fairchild and his associate, Ingrid, showed up. I took them to my office and sat down with them. Sitting made me notice the plug. A few minutes later as he was explaining his business offer, I shifted in my seat. The damn plug started vibrating!"

Cassie looked over at Angie who was smiling. "Oh no! Then what?"

"Then what?" Kylie raised her voice. "At first I thought they could hear it but they didn't seem to. Then it began to feel a little too good. I couldn't sit still. And all that movement caused the plug to start pulsing!"

Angie started laughing.

"It was no laughing matter!" Kylie exclaimed. "I couldn't even concentrate."

"Sorry," Angie said. "Just picturing it, it is kind of funny. What did you do about it?"

"I excused myself and went quickly to the bathroom. I took down my panties to find my cock rock hard and covered with pre-cum. The front of my panties were soaked."

"Then what?" Cassie asked. "Did you, you know, take of business?"

"No! There wasn't any time. I reached behind and took the damn plug out! Then I returned to my office and finished up with Mr. Fairchild. He asked if I was all right? Except for having an throbbing hard-on, I was fine!"

Explaining it didn't make Kylie less angry.

Cassie smiled. "That's too bad. I played with the settings. They felt good. I think I came three or four times."

"Wonderful. Good for you." Kylie's voice dripped with sarcasm.

"Well sweetie, it looks like Cassie kept her in longer. You lost." Angie looked at Cassie then Kylie and smiled. "I guess there need to be some consequences."

"Oh great! I can't wait," Kylie replied, still angry.

Kylie stood in the shower, letting the hot water cascade over her. She wasn't as angry as earlier but it still bothered her. It bothered her that it could have lost a possible opportunity but more importantly it bothered her that she got so mad at Angie and Cassie. It was a fun idea and it did feel good. It just wasn't a good day for it.

She started thinking what kind of punishment those two were thinking of. They never did any S-M and they weren't into that stuff. Angie could be a little forceful but it was pretty tame stuff. She was sure Cassie wasn't. She was sure Cassie hadn't even thought in that direction.

So what would it be? Using the strap-on again? The butt plug? Kylie was sure it would be something like that and the thought excited her.

Kylie walked out the bathroom and into the bedroom. What she saw caused her to stop. Standing either side of the bed was Cassie and Angie. Both were dressed in black bra, black panties, and stockings held up by a black garter belt. The look made her smile.

"Are you ready for your punishment?" Angie asked.

Kylie knew the drill, "Yes, Mistress!"

Angie smiled, happily knowing Kylie was ok with what was going to happen. Maybe?

"Lie on the bed on your back. Arms stretched out," Angie commanded.

"Yes Mistress," Kylie said as she did what she was told.

Both girls climbed on the bed and knelt on either side of Kylie. "You have failed us. Are you willing to be punished?" Angie intoned.

At this point Cassie laughed. Angie shot her a dirty look.

"Yes, Mistress."

"Good. Bring your knees up and spread your legs."

Kylie did as she was told. She felt the coolness of the lube being rubbed on her asshole. She also felt some being applied to her cock and a pair of hands stroking it and massaging her balls. It felt good.

After a few minutes she could feel Angie inserting the plug in her ass. Again Angie took her time, going in and out slowly before totally sinking it in. She pushed the button and the vibrations began. Kylie moaned.

Cassie gripped Kylie's balls and slightly pulled them away from her body. She slipped a ring around them, holding them there. She then slid the cock ring to the base of Kylie's cock. When done she slowly stroked Kylie's cock to hardness. "Does that feel good?" she asked.

Kylie groaned out, "Yes!"

The two girls now moved up and began to kiss and nibble on Kylie's neck while each played with her nipples. Kylie squirmed as the sensations coursed through her body.

"Do you like it?" Angie whispered in her ear.

"Oh yes," Kylie responded

Angie pinched Kylie's nipple. "Yes, what?"

The sudden jolt of pain caused Kylie to arch her back. "Yes, yes Mistress!"

Cassie and Angie began to suck on Kylie's nipples adding more sensations to her body. Angie reached down and pushed the plug's button a few times, reaching a new setting. It now vibrated harder and pulsed.

Kylie's mind was now being overwhelmed with feelings of pleasure. Her body tingled with excitement. The new feeling in her ass caused her mumble, "Oh fuck! Oh fuck!"

Cassie lifted her head from Kylie's breast and looked at Kylie's cock. She nudged Angie to take a look. What they saw made them stare.