Claire and Emma Have a Night Out

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Emma wants to be more like her former boss Claire.
4.2k words
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Part 2 of the 4 part series

Updated 08/11/2024
Created 07/06/2024
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Claire and Emma Have a Night Out

"Nervous?" Claire asked.

"Incredibly," Emma replied.

"I'll be by your side the entire time if you want me to be. You've got this Emma."

The two were in Claire's car, heading to a party. Claire wasn't nervous. She was looking forward to getting reacquainted with old friends.

"Tell me again how you knew about this party and how you know these people." Emma said.

"I dated a man who introduced me. I went to a couple of parties but didn't get a chance to really explore. The relationship didn't last because I was putting my career first. He and I stayed in touch. I met some great people and have gotten invitations occasionally, but this is the first time I've gone back."

"I can't believe we're going to a swinger party." Emma said.

"Well they don't really call it that. There is usually a theme, like tonight is a lingerie party. It's a tight group of people. Some are married couples or in relationships, but not all of them. New people are invited occasionally but they have stayed pretty exclusive and everyone has stuck to the rules."

"No telling, right?"

"That's a large part of it, Claire said. "No one talks about what happens at the parties except at the parties. There aren't many secrets among the group, however. Like I mentioned before, everything must be consensual. If you don't want to be watched, keep the door closed, and never enter a room unless the door is open."

Claire had been Emma's boss before a corporate buyout had split them and the rest of their tight knit-team up. They had all stayed in touch and recently gotten together for a cookout at Claire's house. It hadn't been planned but the group celebrated Nude Day in grand fashion.

"Have you talked to Asher lately?

Asher was one of Emma's former coworkers and Claire had been his boss, too. Claire and Asher developed a special connection at the party.

"Ash knows where I'm going tonight, if that's what you're really asking. Under that quiet exterior he is a confident man. Do you know he's been accepted into grad school?"

"Really? That's awesome. Way to go Asher."

"He's camping this weekend," Claire said.

"Asher camps? I cannot picture him roughing it." Emma said.

"That's what I thought too! He and a group of his college friends go every summer. From what I gather there is a little debauchery mixed in."

"And you're okay with that?"

"I am. He will be seeing his college sweetheart, and I told him whatever happens to just go with it and we'll talk when we see each other next. He told me to have fun and said he's good with whatever happens, too."

"And you believe him?"

"I do. We agreed that as long as we were 'safe' we should each enjoy ourselves."

"So you have a green light tonight?" Emma asked.

"Young people," Claire said exasperated. "Always making things sound so trashy."

"A green light isn't trashy. Now if I called it a hall pass, that would be trashy," Emma said.

"Tonight is about you, Emma. I'm not sure I'll be letting my hair down. "

Claire turned onto a long driveway. A large mansion-like house came into view. "We're here. Are you ready for this? If you're uncomfortable at anytime we will leave. Just say the word." Claire said.

"I'm ready. I want to have the confidence you do, Claire. And if I decide to go through with what we talked about, you're really okay with that?"

"I'm good with whatever you decide. I know from experience now, that a threesome can be wonderfully intense. If we find partners you're comfortable with, and you are sure, I will do everything I can to make sure it's everything you hoped.

#

Claire and Emma were met at the door by a couple appearing to be in their late 50s. The woman was wearing a sheer nightie, the outline of her areolas and nipples visible. The nightie was short and she wore lace panties.

The man was dressed in a loud print shirt, unbuttoned nearly to his waist, and blue dress slacks. "Welcome. It's good to see you again, Claire. I was so happy when I heard you were coming. And you must be Emma. I'm Phil Barnett, and this is my wife Anne," he said.

"Come in and make yourself at home," Anne said. "I'll show you where you can change."

Anne led the two friends to a dimly lit room off the main entrance. There was a king sized bed, oak dressers, a walk in closet, and a door leading to a large en suite bathroom. "You can put your clothes in the closet," Anne said.

When they were alone, Claire removed her three quarter length jacket, revealing a blue corset, garter belt, and matching stockings. When Claire walked to hang her jacket in the closet, Emma saw she was wearing a g string. She looked stunning.

"Claire! You wore that on the drive here? You really are the sexiest woman alive."

Emma stood by the bed naked. She was large breasted with large pink nipples. Her waist was small, her tummy flat. Her hips were wider than Claire's, but in no way out of proportion to the rest of her body. A thatch of red hair covered her pubis.

"Will you help me with this damn thing, Claire?" Emma held a tangle of fabric in her hand.

It took some effort by both of the women, but soon Emma was resplendent in her outfit. The bright pink looked great against her red hair. Thin straps came to a cupless bra. Each of her nipples were covered by a small bow. The rest of the top came just below her navel. Pink lace cheekie panties completed her ensemble.

"Come on," Claire said. "I was told there will be a few new faces here, but I will introduce you to everyone I know."

The lights were low in the main part of the home. Lighted candles gave the room a glow. Men and women with drinks in their hands were talking in small groups. A table with a dozen opened wine bottles stood next to a stocked bar area. It would have seemed like a usual cocktail party, but for the large bowl filled with condoms sitting on the bar.

"Claire! You look ravishing as always. I'm glad you decided to join us." The man speaking was medium height, appeared to be in his early 40s, and had a winning smile. His hair was dark brown starting to go grey at the temples and he was clean shaven. He was wearing a blue sports coat over a white shirt with tan chinos.

"Hello Steven, it's great to see you in person after so long," Claire said as the two hugged. "Steven, this is my dear friend Emma. I mentioned her when we spoke on the phone. Emma this is my friend Steven."

He stuck out his hand to take Emma's. It's Steve, actually. Claire is the only one who can get away with calling me Steven. May I get you a drink? Phil and Anne made sure the bar is well stocked. He raised his orange drink garnished with orange slices and a cherry."

"Whatever you have looks great," Emma said.

"I would be happy to make you one, but there's no alcohol in it. I don't drink, myself." He said.

"Well I'll have what you're having, if you don't mind adding a generous portion of vodka. Is that okay?"

"Of course. And Claire? Is it a red wine or martini night for you?"

Claire practically sparkled in the candlelight. Her blue corset matched her eyes perfectly and complimented her blonde hair. "Martini, extra dirty. Thank you Steven."

While Steven was getting their drinks, Emma said, "Wow Claire. He is the one you dated? I should have known he would be drop dead handsome."

"He is. And he is, isn't he? I really don't like thinking of it as shopping for partners, but what do you think? Should we put Steven on your list of possibles?"

"Oh Claire, he's gorgeous, but I wouldn't do that. It's obvious there is still a spark between you. And he is quite a bit older than me."

"Steven is a good man, Emma. I'm suggesting it because I know he will be open to the idea. And I trust him. More importantly, I trust him with you."

"Alright, let's mingle a little more before I decide."

Emma was amazed how casual and friendly everyone was. The group ranged in age, although of the 30 or so people, she was among the youngest. People flirted openly, but Emma heard no overtly sexual comments.

A younger man kept catching Emma's eye. At first she thought it was because they were close in age, but the more she looked his way, the more she was drawn to him. He was very good looking, but in a subtle way. He had dark hair and dark eyes. He wore a neatly trimmed goatee. His smile revealed perfect teeth. He carried himself in such a way that communicated he was comfortable with himself rather than full of himself.

"Do you know that guy over there, Claire? Emma asked.

"I don't. I heard he is a friend of the Barnetts and that he has been to a few parties. Go talk to him."

"Will you come with me?"

"No Sweetie. I will if you really want me to, but just be confident and say hello. If there's a connection the conversation will take care of itself. I don't think you realize how sexy you are. I'm sure he would love it if you talked to him."

The man was in a conversation with Phil Barnett when she approached. "Emma, hi! Are you having a good time? This is Sawyer, he's a good friend of Anne's and mine." Phil said. "This is Emma."

Instead of shaking her hand, Sawyer gave Emma a friendly hug. The gesture was in no way uncomfortable for Emma.

"How do you know each other?" Emma asked.

Sawyer hesitated. "It's sort of a long story, actually," he said.

Phil laughed. "But it is a funny one. Let me get Anne, she tells it the best."

"I kept waiting for a chance to break away and talk to you. This isn't how I hoped our first conversation would go." Sawyer said.

Phil came back with his wife in tow. "Sawyer. Emma. I was hoping you two would get a chance to meet." Anne said.

"I never get to tell this story except to people in this group. Sawyer grew up in the neighborhood and showed up asking if we ever had odd jobs that needed to be done. He was saving for his first car. He was so sincere. We hire a lot of the work around here done anyhow, so told him to come back Saturday morning.

"Anyhow, Sawyer was the hardest worker. It didn't take long before he had replaced our usual yard help. We loved having him around. He was always so respectful. One day he asked if he could use our pool. Of course, we told him he could use it anytime he wanted as long as we weren't entertaining. If we're not home, just let yourself in, we said. Sawyer worked for us all through high school.

"Fast forward to the summer after his freshman year of college. Phil and I had been out, and Sawyer walked over to see if we had anything that needed to be done. Since we weren't home, Sawyer decided to take a quick dip in the pool. He hadn't planned to, so of course he didn't bring a suit.

"When Phil and I got home we had no idea Sawyer had just finished skinny dipping. I took my clothes off and went out back for a swim myself. Sawyer and I nearly bumped into each other, both of us naked. Then here comes Phil out of the house and he isn't wearing anything either.

"Of course we didn't care that he was swimming nude. We told him he could use the pool anytime and wear whatever he wanted. But we didn't see him again for a whole year! The poor guy was so embarrassed. Summer break of his sophomore year there's a knock on the door. It's Sawyer asking if he can use the pool. Of course! Then he asks if he can swim nude. Of course! Phil and I don't care. It's not like we are going to spy on you when you do I said.

"After his junior year he comes to ask again. No one answered the door so he came around to the pool. He finds me laying by the pool reading a book and of course I wasn't wearing anything at all. I tell him to swim and do his thing, I won't bother him. Phil came home and finds Sawyer and I drinking lemonade by the pool in our birthday suits and strikes up a conversation. Later Sawyer asked me if Phil would be mad because we were hanging out naked together. I say hell no, it probably just adds fuel to his cuckhold fantasies. Well, you know 21 year old men are all hormones. Long story short, it wasn't the first time Phil watched me with a younger man, but I think it was the most fun. Sawyer came back after he graduated and we popped his threesome cherry."

Phil and Anne broke away to talk with other guests. Sawyer and Emma were alone. Emma broke the awkward silence. " I think that's a pretty cool story."

"Are you being serious?"

"I am. So you were in a threesome with the Barnetts? That's pretty hot, actually."

"Well, yes. And you do?" Sawyer said.

"I'm going to check in with my friend for a bit. I'll be back."

"I'll be here," he said.

Emma left Sawyer and found Claire.

"Emma, how are you? Everything alright?"

"I'm really good Claire." Did you here the Barnetts tell that story.?"

"I did. Sawyer is pretty damn cute. I like the way he carries himself. But what's your reaction to the story?"

"Based on his hotness quotient and prior related experience, he's definitely on my list."

#

Emma saw couples kissing. There was also some petting going on. The sexual energy in the room wasn't lost on Emma and she found she enjoyed it. She was looking forward to joining in, but didn't know how to start. Claire had introduced her to a lot of people and she found them all approachable and easy to talk to. She was comfortable with her surroundings now, but still thought it odd the women were in lingerie but the men were more formally dressed.

Emma heard the clinking of silverware on a glass. Everyone looked at the source of the sound. It was Anne.

"Gentlemen, we have reached the magical hour. Our invitations indicated how Phil and I planned to have the evening progress. We hope you have enjoyed seeing all our female guests in their beautiful lingerie. This may be a change from our usual theme nights, but I promise we are all looking forward to your return. We will be here waiting."

All of the men left, leaving the women alone. Emma looked at Claire who just winked at her and smiled.

The men began returning, every one of them naked. Emma had never seen so many naked men at once. She hadn't been expecting this, and laughed to herself that Claire had known but hadn't shared the information. She realized she was unabashedly looking at each man as they returned.

Phil Barnett was the first back into the room. He had the largest cock Emma had ever seen, although she didn't find the size overly appealing.

She saw Claire's friend Steve, and he looked as good out of his clothes as he had been wearing them. He had a smattering of light chest hair, that like his temples, showed hints of grey. He exuded confidence showing no sign of modesty. I bet all of Claire's former lovers were that hot, Emma thought. He crossed the room and kissed Claire. Emma admired his ass as he did.

Sawyer walked into the room. And wow...he was seriously cute. He had a great chest and shoulders. His physique looked like it came naturally rather than from a gym. Probably all the years of yard work. She thought his cock much more inviting than Phil's. It swayed a little as he walked. He headed straight to Emma and asked if he could get her another drink. Emma shook her head. She continued to admire his body, and Sawyer didn't seem to mind. Claire always told her to be confident. Emma was determined to enjoy all that was happening tonight. Before giving it much thought she kissed Sawyer's lips.

"Would you like to go somewhere more private to talk?" he asked.

"I would like that very much. Although, looking at you now, I'm not sure I will be in much of a mood for talking." The two kissed some more. Emma decided to take the initiative and tell Sawyer about her goals for the evening. She wasn't sure how he would react, but she was hopeful. Sawyer smiled and nodded. They walked hand in hand and approached Claire and Steve.

Emma did the talking. "Hi Claire. Sawyer and I are going to find someplace away from the crowd. We would really appreciate it if you would join us. We would love it if you came too, Steve. If you want to, that is."

"Yes, of course Emma. Will you join us Steven?" Claire said.

"Is this the possible scenario we discussed Claire?" Steve asked.

"Yes, I believe it is," Claire said.

Steve turned to Emma. "Emma. You are a very beautiful woman and Claire speaks highly of you as a friend. I'm honored you've chosen me to spend time with you tonight. I'm sure I speak for Sawyer, as well, in saying how much we are looking forward to the evening ahead."

"I've pulled a string or two," Claire said. "There is a room waiting for us with a feature I think you'll find intriguing."

The room was like something out of a magazine. Everything was lovely and looked...expensive. A queen would be more at home here than Emma felt. There was a day bed, a couch, and king bed. And it couldn't be. Emma had heard people joke about this, but never dreamt it existed in real life - there was a mirror on the ceiling above the bed.

When all four were in the room Claire closed the door.

"Thank you," Emma said. "As exciting as the thought is to me, I don't think I'm ready for a larger audience."

"You're in control Emma. If anything happens that makes you uncomfortable, say so. If you want to stop, these gentlemen will respect your wishes."

Claire walked to the two men and took a cock in each hand. She kissed each man on the lips, then turned to Emma and kissed her on the lips as well. She whispered in Emma's ear so the men couldn't hear. "It's your show. You are in control. And, Sweetie, remember to enjoy yourself."

"Okay...silly question. How do things get started?" Emma asked.

"I would start by putting my tongue down that cute Sawyer's throat, personally. I know you can master a cock. I'm confident you can master two equally as well."

Emma approached Sawyer and began kissing him. She ran her fingers through is hair then over his shoulders. She felt him harden as she ran her hands down his back and over his ass. Claire was impressed when Emma then began kissing Steve while stroking Sawyer's cock with her right hand. Steven was hard and she stroked both men as she went back to kissing Sawyer.

With a cock in each hand, Emma kissed Sawyer's chest, then his stomach. Before long Emma was on her knees in front of the younger man. He took a deep breath and exhaled with his eyes closed, face turned to the ceiling, as Emma took him in her mouth. She never for a moment stopped stroking Steve with her left hand. Her head moved in a steady, slow rhythm as she worked Sawyer's cock.

Emma then turned her attention to Steve. She licked his pouch, and took one of his balls into her mouth as her hand stroked his cock. Her right never stopped stroking Sawyer. Soon her mouth was working Steve's shaft.

Both men were similar in size with Steve only slightly thicker than Sawyer, Emma observed. A perfectly matched pair, Emma thought as she smiled to herself.

Claire grinned when she heard a long "mmmmm" from Steven. He opened his eyes and turned his head Claire's direction. Claire winked at him and mouthed "told you."

"You three may be more comfortable on the bed," Claire said.

Emma stood and began kissing Sawyer again. Steven delicately began undoing the clasps on the back of Emma's pink lingerie top. She moved her arms and the top slid away to reveal her large breasts. Her nipples stood erect in the middle of each half dollar sized areola. Sawyer began kissing her breasts greedily, caressing them with his hands as he did. When he stopped, he looked Emma in the eye for a moment then slid her cheekie to the floor. When she stepped out of them Claire saw the fabric was wet.

Both men's mouths were exploring Emma's body when they were on the bed. Emma was loving the feeling of their lips and tongues on her. It was Sawyer who moved to begin using his mouth and tongue between her legs first. Steve was kissing her breasts, then positioned himself beside her head. She turned to face his waiting cock and took him into her mouth. Emma opened her eyes and saw the scene reflected above her. In the mirror she saw that Claire was fondling Steve from behind, her hand between his legs.

12