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Jill's First Swinger’s Party

"Jill let's loose at the party while her boyfriend watches"

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As Jason pulled into his boss’s driveway, he couldn’t believe he was there. Sitting beside him was his beautiful girlfriend, Jill. He would never have believed that she would agree to attend one of his boss’s notorious parties.

Jill had grown up very conservative with a super strict mother. With her good looks there was no doubt that many guys had tried to get into her pants, but Jason had been the first and the only, and that was not until they had dated for a year.

So to see Jill all dressed up and willing to go to the party had been a surprise to him.

He believed her decision had stemmed from her conversation with another couple from work that they knew. Her friend, Sue, had told her about the parties and said they could be lots of fun.

But she had also assured Jill that no one had to do anything they would rather not do.

Something else she had said had stuck in Jill’s mind too, “It can’t do anything but help Jason’s career advancement.”

She had wondered if that could really be true. But the more she thought about it, she realized that other men had received promotions that she thought should have gone to Jason.

“We’re here,” Jason somewhat nervously said, “Are you sure you are okay with this?”

“I should be fine,” Jill replied,

“Sue has told me a bit of what to expect.”

Jason looked over at his girlfriend and was proud of her. He didn’t think she realized how stunning she was. He had often noticed that her hot figure accented by her nice tits and her sexy hair had caused men to look her over. He couldn’t imagine any man not wanting her. That wasn’t the question.

The question was: How far was she willing to go? They had talked about it the night before and Jill had admitted that she had let some boys play with her tits and even finger her pussy when she was in school, but that was as far as she had ever gone with another guy. He knew she had never even sucked a cock because she had always refused to do that even for him. He worried a bit that some guys might get upset with her if she refused to play much at the party.

They were greeted at the door by Jason’s boss, Ken, and his wife, Linda, who immediately offered drinks. Ken and Linda were an attractive couple in their mid-fifties.

Ken was a bit tall and quite tan from playing golf all the time. Linda was a more petite brunette with a very buxom figure. As they entered the large family room, Jason and Jill realized quite a crowd had already gathered.

Jason counted eight couples and four or five single men. He couldn’t help but wonder if his girlfriend would be interested in any of the men there.

It wasn’t long before Linda said, “May I have your attention, everyone? Everybody is here now, so I think it is time to mingle. But first, I want all the ladies to come with me, and we’ll all change into something more comfortable.”

This was the first moment of truth for Jill. Jason held his breath and was a bit relieved when Jill got up and followed the other women to another room. He had another drink and waited anxiously for the women to return.

In about fifteen minutes, he heard a door open upstairs and some women laughing, and he knew they were headed downstairs. He immediately tried to pick out his girlfriend in the group.

His eyes lit up when he saw her descending the stairs dressed in a very short sheer black dress showing her bare shoulders with what appeared like sexy black stockings on her legs.

Jason realized it was sexier than anything she would have ever picked out for herself.

As she sat on a sofa across the room, Jason’s eyes nervous glanced around and noticed that several men were looking at her. For her part, she seemed to gaze about without making direct eye contact with anyone.

Linda got everyone’s attention again and said, “Okay, you all know the rules. No one has to do anything they would rather not do. No, definitely means NO. We want everyone to have fun, but to make sure the rules are followed, please remember that the rooms are being monitored. If you violate this rule, you will be asked to leave and not be invited back. So that being said, everyone, have fun!”

After her announcement, Linda came over and sat by Jason. “I think everything will be okay. I believe Jill will play a little bit, and you can too if you’d like.”

“I am not so sure,” Jason replied.

“If she doesn’t play with anyone, then I certainly won’t be doing it. I imagine that would upset her.”

“Well, take a look. It looks like she’s not wasting any time.”

Jason turned around and saw his girlfriend headed up the stairs hand in hand with another man. His mind began to race. He wondered if she would do anything? What might she do? Would the man get upset when he found out she wouldn’t do much?

When he turned and looked back at Linda, she took both his hands and said, “Don’t worry. She’ll be fine. Why don’t you come with me and that will take your mind off her?”

As she stood up, she pulled him up and guided him to the master bedroom on the first floor.

When they arrived in the bedroom, Linda sat down on the bed and patted beside her. She could tell that Jason was still worried about his girlfriend. “Really, she’ll be okay. You don’t have to worry,” she tried to calm him.

“It’s just that she’s never done hardly anything with another man,” he responded. “I don’t want him to get upset with her and either harm her, or embarrass her.”

“Would it make you feel any better to know for sure that she was okay?” Linda asked.

As Jason meekly nodded yes, Linda picked up a remote control and clicked on the TV.

“Remember that I said all activities are monitored for safety?” The TV screen lit up and Linda changed the channel. Jason gasped when he realized he was watching Jill and another man in a bedroom.

Jason watched as his girlfriend sat on the bed with another man. They were both still dressed and simply chatting.

“That’s about what I figured she would do,” Jason told Linda.

“Well, let’s just wait and see. They’ve only been there for a few minutes,” Linda replied.

After a few moments, Jason realized the man was going to try to kiss Jill. He felt sure she would push him away. To his surprise, she opened her arms and lay back on the bed while returning his kiss. He reasoned that a little kissing was fairly innocent, and she was probably okay with that.

His eyes widened when he saw the man’s hand slide up and cup her breast, and she made no attempt to push it away.

Jason heard Linda whisper softly, “Hmmm, it looks like maybe she is going to enjoy the evening.”

He responded, “Well it’s just a little petting. Pretty innocent in the scheme of things.”

Jill was returning the man’s kisses quite passionately. She didn’t resist when he slipped his hand inside her top and began fondling her soft tit. That sight caused Jason’s cock to stiffen and as he shifted a bit on the bed.

Linda teased, “Are you finding this arousing?” He kept his eyes glued to the TV and only mumbled a little.

Jason continued to watch as the man fondled his girlfriend’s breast. By now he had worked the top of her dress down and her tits were completely exposed. He heard his girlfriend moan through the TV speaker as the man leaned forward and started sucking on her erect nipple.

Jason couldn’t believe that his girlfriend was allowing this stranger to play with her like this.

He saw her wrap her arms around the man’s neck and pull him tighter against her. As the man slid his hand down between her thighs, he realized she was opening her legs for him. His hand pushed up under her dress and Jason realized Jill was wearing black bikini panties with a high waistband that allowed the man to start fingering her cunt.

“I’ll bet you could use some help,” Jason heard Linda say as she unzipped his pants, reached in and pulled out his cock.

She slowly began to stroke his hard cock, which caused him to groan. Back on the screen, Jason watched in amazement as the man had slipped Jill’s dress down over her hips and she slipped out of it. He saw him move down between her legs and looked at Linda and said, “This is where it will stop”.

“She never lets me eat her pussy. She says it’s nasty.” But instead of pushing him away, Jill opened her legs even wider and arched up when she felt her new lover’s tongue licking her pussy.

From the rocking of her hips, there was no doubt she was enjoying it. The man feverishly licked her pussy as Jill cupped her tits and played with her nipples, pinching and pulling them, all the while with her hips rocking and pushing back into the man’s face.

“Oh my… Oh, my…”, Jason heard his girlfriend shriek through the TV speaker as she grabbed the stranger’s head and held it to her pussy and pushed back hard as her body shook wildly and her toes curled.

“I have never felt that before!”

“You’ve never felt a tongue on and in your pussy?” her lover inquired.

“Well yeah, that too…but I have never ever cum before. I have only read about it,” she gasped.

Her lover laughed, “Really? Well, I am glad to be the first man to make you cum. Do you mean your boyfriend has never given you a climax?”

“No, he hasn’t. He only fucks me, but he's not that big, and I have never had an orgasm from that. So I didn’t realize how good a climax would be.” And with that, she collapsed back onto the bed, still breathing heavily.

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Jill didn’t even realize it as her partner finished removing all his clothes and lay beside her. She cuddled up against him and smiled.

“Thank you so much. Can I give you a hand job?”

“Sure,” he responded as he rolled more onto his back. He appeared agreeable to accepting whatever she offered.

Jason watched his girlfriend grasp the man’s stiff cock and slowly stroke it. Simultaneously Linda started stroking Jason’s cock, matching the action on the TV screen stroke for stroke. She looked at Jason and said, “I think your girlfriend is going to get fucked tonight.”

He looked at her and replied, “I doubt that. All she has offered is a hand job, and I’m even surprised she did that.”

As he looked back at the TV, he saw Jill shifting and couldn’t believe his eyes.

He watched as his girlfriend, who had never sucked his cock before, wrap her lips around her lover’s cock and slowly slid her mouth down over it.

He was confused and excited at the same time. “She has never done that for me,” he whimpered to Linda who didn’t say a word but in response simply leaned forward and took his cock into her mouth.

“Ohhhhh,” moaned Jason. He leaned back a bit, watching his girlfriend sucking another man’s cock while Linda sucked his.

He could see that the man was really enjoying having his cock sucked by his girlfriend, when all of a sudden she pulled off and lay beside him.

He thought, “Uh, oh,” he’s going to be mad at her for stopping.

However, Jason watched in disbelief as the stranger moved up and over Jill. Instead of pushing him away, she spread her legs apart and wrapped her arms around him.

“Nooooo,” thought Jason as he watched the other man’s cock sink into his girlfriend’s waiting pussy. He could see that her pussy had stretched wide to accept his thick cock, and as it pumped into her, he could see her glistening juices coating her lover’s cock as he pulled back out.

Slowly at first, he began to fuck her, sliding his large cock all the way in and then nearly all the way out. He could hear Jill grunting through the TV speaker.

Then he heard her speaking, “Fuck me, oh fuck me. Yes, like that. Oh, you are fucking me so much better than my boyfriend …your cock is SO much bigger than his” as the man started to thrust into her faster and more vigorously.

He watched as she kicked her legs even further apart and held them high and moaned, “I’m cumming, yes, yes, yes.”

She continued to breathlessly gasp,

“That was the first time…. I’ve never had that happen before…. I never knew I could do that.”

Her breasts rolled as she heaved and panted. “Oh, thank you, thank you,” she told her lover.

The entire time she was in ecstasy, the man had continued to fuck her. All of a sudden, he groaned and jerked forward, and Jason realized that he was emptying his balls into her.

The realization that another man was cumming in his girlfriend’s pussy was more than he could handle, and his cock exploded into Linda’s mouth.

Linda swallowed Jason’s load of cum like a pro and then smiled at him and asked,

“Did you like that?”

He replied, “Oh yeah, I’ve never cum in a woman’s mouth before. That felt so good!”

Linda laughed, “Well I am glad you enjoyed that, but it’s not what I really meant. I wondered if you liked watching your girlfriend sucking and fucking another man.”

“It was the hottest thing I have EVER seen,” he responded. “I never thought she would ever do anything like that. Plus, it looks like she actually enjoyed it.

“Oh yeah,” Linda laughed softly, “I’d say she definitely enjoyed it.”

The entire time Jason and Linda had been chatting, the man who had just fucked Jill had been getting dressed. Jill was still basking in the afterglow of her first orgasms and had simply remained lying in the bed.

“I am going to slip on out,” the man told Jill “You were great. I hope we can do this again.”

Jill smiled back and simply replied, “Yes, me too.”

She lay there in bed, catching her breath as she watched the man leave the room.

Just as Jill was ready to get up to start to get dressed, she saw the door opening again. She pulled the sheet up over herself instinctively to cover her body. When she saw that it was the host, Ken, she relaxed a bit but still kept herself covered.

“I’m just checking on you since I know this is your first swinger’s party. Is everything going okay?”

“Everything is just fine,” she giggled.

“I was never really expecting this, but I am so happy we got invited. I hope Jason is having a good time.”

“Oh, I imagine he is,” Ken replied. “I suspect Linda is taking care of him. She likes to welcome newcomers, just like I do.”

Of course, he knew where the hidden camera was, and he looked right into it and winked.

Jason had to stifle a laugh. “You two are something else,” he told Linda.

“It’s all in good fun,” she responded.

“And best of all, the night is still young!”

“Well, I don’t know how much more Jill might want to do. This was a pretty big step for her.”

“Why don’t we wait and see.”

As she spoke, she nodded toward the TV screen.

Jason hadn’t been paying any attention to what had been going on in the other room, but at Linda’s prompting, he looked back up at the TV screen.

He was surprised to see that Ken had removed his shorts and was standing at the end of the bed. But he was more surprised to see Jill was sucking Ken’s stiff cock.

She had moved to the edge of the bed and was sitting there at the perfect level for his cock.

Jason watched in amazement as his girlfriend was sucking her second cock of the night.

“Are you sure she has never sucked another man’s cock,” Linda asked. “She looks pretty good at it to me! She must be a natural.” Linda giggled.

“Well, she had never sucked my cock before, and she said she had never sucked another man. But now I am beginning to wonder.”

Jason felt like he was watching a porn star as he watched his girlfriend worshipping Ken’s cock.

She would slide her tongue up and down his shaft and then swirl her tongue around his cock head. He also saw her cup Ken’s balls and hold them and squeeze them gently. He noticed Ken really seemed to enjoy that.

Watching Jill service another man started to have an effect on Jason again.

Linda noticed too and teased him, “It looks like someone is enjoying watching his girlfriend suck cock.” He could only smile back at her.

“Well, you know, so far, I am the only one here who hasn’t gotten fucked tonight. I think it’s time we took care of that.”

She took Jason’s hand and guided it to her pussy.

“See, I find watching arousing too. Can’t you see how wet my pussy is? Why don’t you lay back across the bed, and we can still watch the TV while I ride you.”

She didn’t have to tell Jason twice. As Jason laid onto his back, he felt Linda slowly stroking his cock.

"Yeah, you’re ready again!” She moved up over him and held his cock upright, guiding it into her warm, wet pussy.

As she sank onto his cock, Jason smiled up at her. Then he reached up and cupped both of her tits.

“Thank you so much,” he sighed.

She just smiled and started riding his cock. As they fucked, they both looked over at Jill and Ken. Jill was taking all of Ken’s cock in her mouth.

Watching him gently thrust into her mouth like it was a pussy was so erotic. Ken was holding Jill's head as he fed her his cock. In and out, he slid in her mouth as her tight lips wrapped around it.

Linda was grinding on Jason’s cock faster and harder. His gaze kept switching from watching her tits bounce to watching his girlfriend sucking Ken’s cock. He knew that it wouldn’t be long before he would cum again.

As he looked back at the TV screen, he saw Ken stiffen, then heard him groan. Jason’s eyes grew big as he realized that Ken was cumming….cumming in Jill’s mouth.

And it appeared she was making no attempt to pull away. He thought he could actually see that she was swallowing.

Once again, the sight before him triggered his climax. He bucked up into Linda and cried, “Oh fuck.”

Linda had reached the breaking point too. Her body shivered as her orgasm took over. Her pussy was spasming and clamping on the cock in her pussy.

She was milking Jason’s cock for every last drop of cum in his balls.

“That was nice,” Linda whispered to Jason as she leaned down and gave him a soft kiss. “I loved watching Jill suck my husband’s cock and swallow his load. And I loved you cumming in my pussy. I am so glad you accepted our invitation to the party. I hope you will keep coming back.”

“Just say when,” he responded as he looked over at the TV and to see Jill.

Jill had finished sucking Ken’s cock and the two of them were chatting.

Jason watched as Ken pulled open a drawer and took out a gift box.

“This is for you,” he said as he handed it to Jill.

“What’s this?” was her reply as she opened it.

Then she exclaimed, “Oh, these are so beautiful! I had noticed most of the other women wearing them and wondered where they had gotten them. It seemed odd that they were all wearing identical pearl necklaces.”

Ken proceeded to tell her, “It’s your initiation gift. It will let the other women know that you are part of the club. To get one they all had to do the same thing you just did…suck my cock and swallow my load.”

Jill blushed but simply replied, “Well, thank you so much. I have had such a good time!”

She smiled back at Ken as he turned and walked out the door. As he stood in the doorway, he winked at her and said, “Well, dear, the night’s not over yet. Keep having fun.”

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Written by Jay35sox
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