A Conspiracy of Circumstances Ch. 05

Derek and Annie were watching “The Walking Dead”/On Demand when Cassie got home a little after 8:00. Annie hit the pause button and said, “So, how was the concert?”

“Amazing, just amazing! We had the best time!”

“My friend Thomas was there,” Derek interjected, “he texted me and said he saw you guys dancing. He said YOU were awesome!”

Cassie glanced at her mother but said to Derek, “What else did he say?”

“Nothing, other than he thought the concert was ridiculously good!”

Annie and Cassie were looking at each other and from the look on her daughter’s face, Annie mouthed the word, “What?” at her.

Cassie just shook her head and said to Derek, “It was! You two watch your show and I’ll fill you in on the details later.” When later came, Annie got the “details;” and halfway through her pussy started throbbing almost uncontrollably!

She had just decided to do something about it when the phone rang...Caller I.D. said it was Jill Hogan. “Hi Annie! I guess the guys got to their hotel okay.”

“Yes, this is a first for Phil isn’t it? He never went along before, did he?”

“No, but apparently these meetings are a big deal. But I’m calling to ask if you wanted to grab something to eat with me tomorrow night. A situation has come up and I need the advice of a friend.”

Annie paused while the memory of what Chris had told her flashed, “Oh? Well I’m not busy right now, Jill.”

“Well, I can’t tonight, but I would rather do it in person anyway if you don’t mind.”

“Okay, no problem; where and when?”

There was a pause, “I’ll pick you up at 5:30; is that too early?”

“See you tomorrow night, Jill!”

Wondering what this was all about, Annie went into her bathroom and sat down on the toilet to pee. She and Jill had been very good friends for quite a while, and they’d had lots of great conversations over the years. They had even discussed their sex lives on many occasions; several of which had been quite explicit. “Yes,” she thought to herself, “unless I miss my guess, this has got to be about Phil’s fantasy.”

She headed back downstairs and found herself alone. Grabbing an apple from the kitchen counter and her phone from the end table, she went outside and sat down on the front porch swing. It was a beautiful night; if Chris were there, she knew she would be snuggling under his arm. The notification “ding” from her phone broke the silence. The text was from Joyce, “Call me when you have a minute.”

When Joyce picked up, Annie said, “I have a minute now!”

“Hi Ann, I was just wondering if Cassie told you about their adventure today?”

She smiled and said, “Adventure? You mean the concert?”

“No, I mean after the concert. Did she mention anything?”

“Well yes, she said they went tailgating.”

Joyce paused on the other end; Annie thought she heard a snicker, “Yeah well, I guess you could call it that!”

Annie burst out laughing and finally admitted, “Yes, Cassie told me all about it; pretty hot I think!”

“You’re a fucking tease,” said Joyce. “But...I think we’ve unleashed a couple ‘hellcats.’ What do you think?”

“It’s too early to tell, but I did warn Cass about moving too fast in these situations; we shall see!”

“Yes, you’re probably right. Anyway, since you know all about it; let me change the subject. What are you doing tomorrow night?”

“I made some plans with Jill Hogan; our husbands are out of town on a business trip.”

“Oh? Well that’s too bad, I bought a new DVD today and I need someone to watch it with. Hey, maybe you and Jill could both come over? I know her fairly well, that might be fun!”

Annie teased her some more, “Define ‘fun,’ please!”

Joyce giggled, “Your mind in the gutter again?”

“My mind? Ha! Between the two of us, who’s the corrupter here?”

“That’s a fair point; I will admit. Wanna come over?”

Annie said, “No can do, Joyce; Jill is concerned about something and needs my advice. She wouldn’t tell me what it was over the phone.”

“Any ideas about it?”

Chris had cautioned her about confidentiality, so Annie replied, “Not really, do you think she might need some sex-pointers?” Both women laughed.

“One can only hope,” Joyce replied, “anyway, it’s an open invitation; I’ll leave the door open for ya!”

Annie sat in the swing for another thirty minutes; she was pretty sure what Jill wanted to talk about. The debate in her mind was over what route to recommend. She mentally played a scenario; Chris coming home one day and telling her he wanted to watch her with another man. “Hmm, this is a tough one!” she said out loud. “What would I do?” She couldn’t think of an answer, so she went to bed.

The next day was uneventful; Annie took a shower at 4:00 and made herself cute-casual. Her friend was prompt and when Annie climbed into the car, Jill was bright and cheery! “Hi you! haven’t seen you for a couple weeks; how ya been?”

“I’m good! Life’s been busy. Derek’s doing so much better, and that’s good; we don’t have to wait on him hand and foot anymore.”

“That’s certainly good news. I can’t say they same, my kids have me running all over the city lately. Maybe they’re overly committed.”

Annie giggled, “We are both servants, we LIVE to serve!”

“Isn’t THAT the truth?”

“So, my sweet friend; what’s on your mind?”

Jill glanced at her and then turned the corner. “Tell you what? Let’s get some food and settle a bit; then we’ll try to sort it out.”

“Okay, is this a problem?” Annie tried to play dumb, “Are you and Phil okay?”

“Oh we’re fine; you’ll see. I just want to run something by you and see what you think.”

When they got seated at the restaurant, they ordered lime rickeys and an appetizer then spent the next fifteen minutes catching up on family activities and interjecting little rumors and gossip here and there. Finally their entrees came and Annie said, “Okay, Sweetie, I’m so ready to hear your story; what’s on your mind?”

Jill had a forkful of salmon. She looked at Annie with a faint smile playing at the corners of her mouth. “I don’t want to shock you, but I really do need some advice; and this is not something I want my mother to know. You’re the only one I’ve ever discussed my sex life with in any great detail, so here we are.”

“I’m the only one? Wow, I’m flattered...I think!”

Jill grinned at her, “What are best friends for, huh? Anyway, a while back Phil shared something with me and, Oh my God, Ann...you could have knocked me over with a feather!”

“What was it? He’s secretly gay?”

Her friend burst out laughing, “Uhh...no! Not that, but it’s pretty shocking. He wants to watch me with another man!” When Annie smiled at her, Jill paused, “You don’t seem so shocked!”

Annie shrugged, “Actually, I’m not that surprised. When people have been married for twenty years, their minds go places. I don’t think your situation is unheard of.”

“Here’s the thing though; he’s brought it up three times now. The last time was just the other day.”

“Wow, okay!” Annie said nothing and they both ate silently for a couple minutes while a “what-to-do” debate went on in her mind. “Jill, I have to tell you something; but don’t get mad, promise?”

“I promise.”

“Chris told me about this a few nights back. They were talking about their fantasies and the subject came up.”

“I’m not surprised that he did; after all, we’re talking about it too, right? But tell me your thoughts here.”

“Honestly, what do my thoughts matter? What matters is what YOU think! Why does Phil want this? Has something gone wrong in your sex life?”

Now it was Jill’s turn to shrug, “I don’t think so; it’s still good! We play together at least twice a week.”

“Does Phil want a threesome with another guy?”

“He didn’t say that, but I don’t think so.” Jill took another bite of her salad, “Frankly, I think he might be too self-conscious for that.”

“What do you mean?”

“Remember? It’s been a few years since I shared; Phil is not that well-endowed.”

“Oh yes! I remember now! You said he was just shy of five inches. Hmm...know what Jill? That might explain why he wants this!”

“It does?”

“Sure! When you two fuck, do you use toys? Like a vibrator”

Jill reddened, “Sometimes.”

“How big is the vibrator?”

“It’s pretty big, eight inches!”

Annie pointed her forefinger at her friend, “There you have it! He likes to see a big dick in you, and now he wants to see the real thing in your pussy!”

Jill placed her plate on the edge of the table. “You think it’s that simple?”

“If he’s a little insecure about the size of his cock, it would explain it.”

“I never even thought about this coming out of any insecurity.”

Annie continued, “There might be another factor or two, but I’m willing to bet it’s the main factor. But let’s be real here; you love each other, and I’m assuming you don’t make fun of his smallish dick.”

“Heavens no, that would be cruel!”

“Would you say Phil is obsessing over this?”

“Obsessing is not the right word, but he keeps bringing it up.”

Staring hard at her friend, Annie probed, “Then WHY don’t you put a stop to it? Tell him you don’t want to do it, and he should not bring it up again!” Jill just looked at Annie; thirty seconds passed and she began tapping her fingers on the table. A minute passed, and Annie said, “It’s because you wouldn’t mind doing it! You’d like to try it!” Jill blushed crimson! “Yep, that’s it; you would like it!”

“I...w..well...uhh,” Jill stuttered, “I...think about it sometimes, I guess.”

“Sure you do! Your husband would like it, and so would you! I’m gonna guess that the only problem is...who to do it with, right?”

Jill nodded, “Yes, that’s it. I told him that. I said I’m not going to go find some stranger off the internet or something; who knows what I’m exposing myself to?”

“Very understandable. Diseases, psycho’s, all that shit!” Annie started giggling.

“What’s so funny?”

“I could just see you asking some guy, ‘Would you like to fuck me? Can you give me three references’?”

Jill laughed as well, “That’s funny, but in a weird way, it’s true!”

“I’ll tell you what’s true; if you put yourself out there, you won’t have any trouble finding a guy. You just want to find the RIGHT guy!” Annie studied her friend for a second. What she said was most certainly true; Jill was very sexy, her face was cute but her body was killer! Even after two children it was clear she worked out to maintain her figure. Annie had seen her so many times in swimsuits, her D-cup boobs, her legs, her ass...just beautiful! And now, with this new-found direction in her own life, she saw Jill in a different way. She was desirable! That thought briefly stunned her and she tried to fight that feeling away.

Jill was oblivious, lost in her own situation. “I guess that’s correct; so what do I do?”

“I don’t know, I’ve never gone looking for another man either!”

Jill grinned, “Maybe Chris knows someone?”

And right then a new, thoroughly devious thought formed in Annie’s brain! “You know what? I have an idea!”

“What is it?”

“I’ll tell you, but only if you intend to go through with Phil’s fantasy; do you want to?”

“I think I do.”

“Okay, you know my friend Joyce, right? Her daughter and my Cassie are besties.”

“Yes, I’ve met her a few times.”

“Yep, well, this needs to be kept secret, but I know Joyce won’t mind if I tell you. She and I have been talking and she confided that she has several ‘lovers’ on the side!”

“Oh my God! Several?”

“Yeah, that’s a long story but I’m thinking she might be able to hook us up with the right guy for you! What do you think?”

Jill sat there thinking, “I don’t think I want one of her lovers.”

“I have to tell you, when Joyce and I started talking about this stuff, it was amazing how much she knows. She’s very discreet; we should ask her.”

Jill smiled, “Okay, I have no objections. Wow, this is moving pretty fast”

“Even faster than you think; Joyce asked me if I wanted to come over tonight since Chris is out of town, but I told her I had plans with you. We could go over there now if you want! Let’s see what she has to say.”

They paid the bill and headed out to the car. Buckling her seat belt Jill said, “Joyce always seemed so...what’s the word...professional to me. How did you two get started on this conversation?”

“I told you it’s a long story, and it has an embarrassing beginning.”

“Wanna share?”

Annie had to consider where this was going, and if she wanted to go there. “Well, her daughter Melanie saw me doing something in the kitchen one day, and she told her mother, and it got the conversation started.”

“I’m going to pry; what were you doing?”

Annie knew she was blushing, “Masturbating!”

Jill’s head jerked sideways at Annie, “Are you kidding?”

“No,” Annie giggled, “I’m not kidding, and one thing led to another and Joyce and I talked about it, and that’s when she confided in me about her affairs.”

“Ohhh, so Joyce is the one that you...” All of a sudden Jill stopped.

This time is was Annie who jerked herself sideways, “That I what?”

“Nothing...I was just wondering, but never mind.”

“You can’t do that, Jill; don’t hang that out there and then not finish it.”

“Annie, I’m sorry...I didn’t mean to say that!”

“C’mon, finish what you said!” Annie insisted.

“When Phil and Chris were talking,” Jill admitted, “Uhh, when they were talking, Chris told Phil that you had been with a woman. I’m sorry, Phil swore to Chris he wouldn’t tell me, but...please don’t be mad.”

Annie wasn’t mad, but she didn’t like the feeling of losing control of her situation; so she just said, “God, life is getting complicated!”

Jill looked relieved, “Oh yeah, most definitely! Look what we’re doing right now? We’re going to someone’s house to discuss finding me another man to sleep with. Would this have ever happened ten years ago?”

“No way in hell,” thought Annie; but out loud she said, “Well, now I guess you can understand why I think Joyce may have some suggestions.”

Jill hesitated, “Can I ask you something?”

“Of course.”

“How was it with another woman?”

Annie studied Jill’s face; but her eyes stayed on the road. “It was so fucking hot; I can’t describe it all that well.”

“Have you been sleeping with women a lot?”

“No, Joyce was the first, but I had been curious for a long time.”

“You never told me that.”

“Why should I? Our lives were good! I had no intention of exploring this curiosity, but it just happened.”

Jill thought for a second, “Just so you know, since the subject has been broached, I’ve never been curious like that.”

“I totally respect that; and just so you know, Chris and I also had a threesome with Joyce! That was equally off-the-charts!”

“Oh my God! You two are something else!”

Annie laughed, “Yeah, we’re scratching things off our sexual bucket list these days!”

“Aren’t you afraid of the consequences?”

“I’m not sure what they are, so no...we aren’t really thinking about them because we reaffirmed our commitment to each other. Did you and Phil discuss ‘consequences’?”

“No, well, other than the perceived dangers of recruiting a stranger. I already told you that.”

Jill turned the corner onto Joyce’s street, and Annie said, “You just have to decide that this pleasure is just for fun, and it has nothing to do with your marriage. Do you think you both can do that?”

“I honestly don’t think I’ll know until something happens. I do want to keep our relationship on solid ground though.”

“That’s the best place to start; always keep that in mind. We’re here!”

Joyce’s front porch light was on; and when they rang the bell, Melanie answered. “Well Hello! This is nice! What brings you here on a Monday night?” When she noticed Jill, she added, “And who is this?”

“This is my best friend Jill,” Annie replied, “we just finished dinner and your mom invited us over.”

Mel opened the door, “C’mon in; she’s downstairs watching TV.” When the ladies entered, Annie saw Jimmy sitting on the sofa; Melanie introduced him, “Annie, Jill, this is my boyfriend Jimmy.

Jimmy stood up, “Hello there! Hi, Ms Hughes! Cassie tell you about the Katy Perry concert yesterday?”

“Oh yes!” Annie grinned at him, “They never had concerts like THOSE when I was a kid!”

Jimmy colored slightly and said, “Maybe not...but they should have, huh?”

Annie and Melanie just laughed and Mel walked them to the stairs, “Hey Mom? Annie and her friend Jill are here!”

From below they heard her voice, “Awesome! Send them down, Honey!” Joyce was waiting for them at the bottom of the stairs and she greeted them with hugs. “Great to see you again, Jill! It’s been a while.”

“It has, over a year I think.”

“Yes, It was at the high school preview day.” Joyce gave a suggestive wink, “By the way, Mel thought your son was VERY cute!”

Jill giggled, “Cute like a puppy? Or attractive cute?”

“Sexy cute! Her exact words were, ‘It’s too bad he’s a freshman’!”

“Wow, okay if I tell him that? No wait...maybe I won’t, we don’t want him getting a big head!”

“I don’t think he’ll have any problem finding a girlfriend someday,” Joyce returned, “assuming he knows how to treat a lady.” Without waiting for a reply, she turned to the TV, pointed the remote, and stopped the movie. “So, I’m glad you both came over; but something tells me you didn’t come to watch this with me.”

Annie and Jill sat down on the sofa and Joyce pulled the wingback chair around to face them. “No,” Annie said while glancing at her watch. “Seeing as there’s little time for small talk; Jill and I were discussing our situations and we think you might be able to help her with this little problem she has.”

A small smile played at the corners of Joyce’s mouth, “Me?” Her eyes darted over to Annie, “How can I help?”

Annie turned to Jill, “She likes to play coy!” Grinning at Joyce she continued, “I told Jill about us; Chris too!”

Appearing to relax Joyce said, “Ohhh, Okay, so she’s already done the ‘freak-out’ then?”

“Nope, no one freaked-out!” said Annie.

Actually, I’m rather impressed with Chris and Annie’s, umm...adventurous spirit!” said Jill.

Joyce giggled, “Me too! It certainly has opened some doors!”

Cutting to the chase, Annie continued, “That’s the thing right there, Joyce. Jill and her husband have an adventure planned also. I mean, they’d LIKE to plan one; but this is a first for them. They need a door to open but don’t know how to open one. Talking about it over dinner, I thought you might have some insights.”

When Joyce heard that, her eyes sparkled and she even licked her lips! “Oh my God, I have lots of ideas! But this all depends on what your interests are, Jill!”

Joyce’s reaction was lost on Jill, but not on Annie. She was going to say something, about her friend being straight, but Jill spoke first, “Honestly, I would have never brought this up, but my husband has brought it up a few times. He wants to watch me with another man!”

“Awesome! I don’t know if you’re aware of this, but that’s quite a common fantasy for a lot of men. So if I’m reading this right, you’d like to know how to find this other man?”

“Yes, that’s it!” Jill leaned forward, “I don’t want to be going on-line or picking up a stranger at a bar; do you know of any other options?”

Joyce looked thoughtful, “If you don’t want to sleep with a stranger, then you’re cutting the options way way down. How many men do you know that might be interested?”

“Holy shit!” Annie interjected, “Look at her! She might get a lot of offers if we advertised!” All three girls giggled at that one.

Joyce narrowed her eyes at her, “Now that you said that, how about Chris?” Annie heard Jill gasp; and when she looked at her, Jill was blushing profusely. Joyce continued, “Before you say no, that would be a huge step...and probably not a wise one unless both couples decided to make this a ‘swinger’ thing.”