Ann: a Love Story

© 2025, All rights reserved -- mimaster

~ * ~ * ~ * ~ * ~ * ~ * ~

Ann was silent as she sat at the table. Chad was just staring at me, smiling as if he was a cat and he'd caught the canary. After what seemed like days with no one saying anything, I finally broke the thick tension.

"What's the big deal about playing a game, Ann?"

She closed her eyes and chuckled to herself; a wry smile crossed her face.

Chad spoke up and said, "It's a little more complicated than that."

"What the hell happened while I was gone?"

Ann opened her eyes and said, "Dana told Chad about what I showed her... and that kind of opened a can of worms."

"What are you talking about?" I asked.

She leaned forward, putting her elbows on the table, making her loose top fall forward slightly. I saw Chad shift in his seat, trying to sneak a peek, but she didn't care. Her mind was on what had happened while I was reading to Dana's girls.

"Remember before, at dinner? We were talking, and Chad said he wondered what it was that made Dana change her mind about being more adventurous."

"Yeah... I remember."

"Well, the thing that changed her mind was... me. And you."

"I'm afraid to ask what that means," I said, taking another gulp from my glass of wine.

"It means I showed her some of the pictures from your trip to West Virginia with Tina."

My eyes flew open. I'm not sure if I smiled, or if it was just the shock of her statement, but she grinned back at me as she put her feet up on the glass table, crossing her ankles as she sipped her Chardonnay.

"You... showed... wait, which ones?"

"Uh... all of them, actually," she said, matter of factly, a hint of a shrug coming from her shoulders. My lengthy silence must have concerned her, because she finally asked, "Are you okay, baby?"

"I'm fine... I just --"

"I know. I'm sorry."

"I'm not mad Ann. Just surprised, that's all. I thought you said earlier that Dana was your role model for being a parent and a slut at the same time. You said she was wild... didn't you?"

Ann laughed and said, "She is wild...

now

... because I showed her the pictures. So, I'm not sorry I showed her, Neil. I'm just sorry I didn't tell you. I don't regret showing her at all... I had to."

"You

had

to?"

"Yeah... I think."

"Now I'm confused," I said, looking over at Chad.

"Don't look at me... I'm confused now too," he chuckled.

"It's what you and I do, Neil. We've kind of touched on it before, but we seem to rub off on people... sexually. I think in a good way. That's the real reason you fucked Carol when you were out there, wasn't it... to help her get past her divorce?"

"Yeah... but it was also because I was supposed to be James Bond, and that's what he does."

"Sure... and I was okay with that, because I set it up. But before me, you and Dawn healed each other, and then there was the woman... the maid at the hotel that you and Dawn helped. And I've done it. There was a time or two after I dumped Ray, but before you came into my life, where I fucked a guy to kind of help him out, which helped me out... so to speak. I mean, I think that's what we do. Just look at what's happened since we've been together. Look at our parents, and your parents' friends, and now my Aunt and Uncle. They've all opened up, and I think that is totally because of us and how we are together."

Ann was right, of course. But I wasn't sure what she was driving at. "Well, there's no argument there, babe. But what does that have to do with showing Dana the pictures."

"Everything. She didn't believe me."

"Believe you? What didn't she believe?"

"I needed proof," Dana said as she stepped back out onto the deck with a white cardboard box tucked her under her arm. It looked like a standard issue board game from either Parker Brothers or Milton Bradley. She put it on the deck floor next to her as she sat down and handed Chad her empty stemmed wineglass. "Ann was right, and as luck would have it, I've never been happier to be proven wrong."

~ * ~ * ~ * ~ * ~ * ~ * ~

Chad had gone inside the house to get another bottle of wine. I didn't drink wine often, which was a shame. I actually knew quite a bit on the subject, but the guys I hung out with were more beer drinkers. I suppose it went with playing in sports leagues. Still, I had an appreciation for good wines, and I always found it relaxing when I had a glass in my hand. I'd been around Ann when she'd had a few beers before, and I didn't know how wine affected her, if at all. Yet like me, she seemed to become more relaxed the longer we sat and talked.

Dana on the other hand, was beyond relaxed. She was loose, and wired... and visibly horny. She had been sitting on Chad's lap, and she had practically been giving him a lap dance in front of us. Not that I minded... Ann seemed intrigued by what Dana was doing, and based on what I saw, I knew she was horny too. But with Chad in the house, the focus of Dana's prurient energy seemed to change from Chad, to... elsewhere.

She looked at Ann and said, "So, did you ask him?"

Ann shook her head and said, "No... because I'm not sure I'm up for this. I already told you that."

"Come on... you're the one that said I was too uptight all the time. Look, we don't have to do it

exactly

like the instructions say. We can do whatever you're comfortable with. But I want to have some fun. And I think you do too. What do you say... do you wanna play?"

I looked at Ann, who gave me a look that was half 'I'm sorry', and half 'I want to do this'... with a little 'I want to fuck your brains out' thrown in for good measure. I was more intrigued than I was confused. I knew whatever it was they were sort of discussing, it was going down the all too familiar path of being sexually charged.

I studied Ann, who sipped her wine slowly, sexily, peering over the top of her glass. Her eyelids were half shut, but her dark brown eyes glowed from the reflection of the Tiki lamps Chad had lit all around the deck. And in those eyes, I could see her passion and excitement simmering just beneath the surface, ready to explode. It just needed to be ignited.

Knowing that, I decided to just relax and trust her. Whatever this was all about was up to her. I'd yet to be upset or disappointed from anything she had set up before, and even though this seemed to be staged by Dana, I knew she knew what was going on. So there was no reason to think this would be any different. Content that she knew what she was doing once again, I was more than happy to go along for the ride.

At least, that was before she grinned at me when she finally answered Dana, saying, "It's not up to me, Dana. It's still Sunday. It's totally up to Neil!"

I felt a lump appear in my throat to go along with the instant pit I got in my stomach. I was suddenly nervous, and I didn't even know what we were talking about yet.

~ * ~ * ~ * ~ * ~ * ~ * ~

"Prove you wrong about what?" I asked Dana as she stared at me over her newly refreshed glass of wine.

She let out a nervous laugh, and Ann said, "Go on... tell him! You brought it up."

Dana took a deep breath and said, "I just didn't understand the whole 'James Bond' thing. It seemed silly to me at first, and Chad was putting all of this effort into helping Ann."

"She got jealous," Chad said with a laugh.

"I wasn't jealous. Well, I guess I was, but not about Ann. I was jealous because you were so excited about what she was doing... and you...."

Chad patted her on her thigh. "I know honey... I was so caught up in it that I didn't give you enough attention," he said, soothing her.

"Well, that's part of it. But you know as well as I do that you wanted that to be you. Ann understood Neil's love of James Bond, and I never bothered to try and understand yours. In fact, I never said this before, but I think

you

were jealous of Neil because he was going to get to live out a fantasy that you wanted for yourself."

Chad looked at his wife, and his expression changed. It was as if he was suddenly enlightened, and that lit up Dana. Especially when he said, "You know... you're probably right. Maybe I was a little bit."

"I think you were... but that didn't stop you from putting all that work in that night for Ann. And I know I got in a tiff about it, but I just didn't get it then. It wasn't until she talked to me about what Neil was doing that I started to. But Ann, you have to admit... setting up Neil for an adventure like that with someone you'd never met? I'm sure you can understand why it all seemed so far-fetched to me."

"Sure, but like I told you then... I've never lied to you, so what would I have to gain by lying then."

"I know that...

now

. And I'm sorry I doubted you."

I thought I had a handle on the entire thing now. Putting two and two together, I hoped I was going to come up with four instead of some odd number. Taking a stab at it, I said, "So, let me see if I got this. Ann needs help from Chad to set up my Bond weekend because she doesn't have enough time to do it herself, plus, he

knows

Bond, so he was the perfect person to ask for help. Chad helps, but he's also a little envious that it's me that's getting his 'Bond' fix stroked instead of him. But in the process, Dana gets ticked because Chad's involved with something for Ann, and it's taking time away from her and the girls... and yet she doesn't get the bigger picture. And in the end, the only way Dana can see the bigger picture is by Ann showing her the actual pictures I sent when it was all done and over. Am I close?"

Chad and Dana nodded, while Ann laughed and said, "Yeah... that's pretty damn close."

"Okay... so I have one question?" I said, looking directly at Dana.

"What's that?" she asked.

"What exactly

is

the bigger picture? What was it you didn't believe?"

"Oh... that," Dana laughed. "Well, it's a couple of things really... but for me, the bigger picture was all about me learning. First, I found it hard to believe Ann was actually letting you go out and fuck another woman. Well... women, really. That was hard to swallow to begin with... until she explained it to me. So, I learned there that I needed to be a lot more aware and understanding of Chad's needs."

"I learned that too... about Dana," Chad chimed in.

"Then, I couldn't fathom how all the things she and Chad came up with actually worked out... I learned a lot more about James Bond than I ever knew. But more importantly, I learned I needed to be more willing to not only accept the things that he likes, but share in them too. You know, find things I like about them, or at the very least, accept that while it's not important to me... it is to him, and respect that."

"Me too," Chad said, nodding as he drank his wine.

Dana smiled at him and said, "And I think I've come to like Bond movies, at least a lot more than I did. Chad even took me to see the latest one. I also learned that I should try to be a lot more inventive. I don't think I'll ever have the kind of mind that Ann has when it comes to this kind of thing, but I never thought to even try before. I felt what Chad and I had between us was good enough. Funny, though... it turned out it was good, but it

wasn't

enough. Then on top of that, Ann asked why I would settle for just good, when I could just as easily have great, or fantastic, with a little effort."

"Or amazing," Ann added as she leaned over and kissed me on the cheek.

"Yes... even amazing," Dana said with a grin. "The point is not to accept less than the best. And I think we were. As for the final piece of the pie, I didn't believe it when Ann told me you and... Tina... that you both helped a married couple with young kids. And that got me thinking about Chad and me. I mean, they're not even his kids, but he's always treated them like they are. And yet, I know he had to sacrifice what he would like, for them... and I didn't see that too clearly."

"I told you Dana, that never bothered me... honestly," he said, trying to make sure I knew he hadn't been whining.

"I know that, sweetheart. And I love it that you never complained. But be honest about it... do you like the way we are now, or the way we were before Ann showed me the pictures and we had our little talk?"

He practically barked out his answer, quickly saying, "Now! No question about it!"

"That's what I thought... so why don't you just be quiet and enjoy the... amazing sex I've been giving you, okay?"

He nodded like a little boy and said, "Yes Ma'am."

Dana giggled and smacked him on his shoulder. Turning to me, she said, "So, now you know. Ann had to show me the pictures, especially the ones of the husband and wife that have the young kids... because I thought it all sounded too incredible to be true. Turns out, Ann is the incredible one."

"Enough already," Ann said, waving off Dana's assertion. "All I did was show a couple of pictures... you've done the rest all on your own, and I think it's safe to say that you have a pretty good imagination too."

"You did more than that, and you know it. But I do feel good about some of the things I came up with," Dana said with a twinkle in her eye.

"I feel good about them too!" Chad laughed, raising his glass in a toast to himself.

~ * ~ * ~ * ~ * ~ * ~ * ~

I swallowed. Not just my wine, which I finished gulping down just as Chad came out of the house with another bottle, pouring me another half glass like he was a waiter. I also swallowed my nerves. The question I needed to ask hung in the air over us. Having just walked out, Chad had the 'what's up' expression on his face, knowing things had changed since he left. Dana was looking at me with anticipation, like a teenager hoping to be asked on a date. Ann was simply smiling, knowing she'd put me on the spot, and wondering how I'd handle it.

Gathering the courage to pull that question out of the air and say it, I glanced first at Ann, who smirked. It was sexy, and it was sending a message. I felt confident that I was able to read her signals pretty well, even though we truly were still getting to know each other. What couple that had been together less than a month wouldn't still be in that 'I wonder what they're saying without saying it' stage? And yet, while I was confident, I was also wary, because I didn't have the details. And the only way to get them was to ask that damn question now dangling from the tip of my tongue.

"So, you want to play. Why do I get the impression we're not talking about a board game any longer, Dana?" I asked, making sure I directed the question exactly to whom it needed to be asked.

"No, it's a board game. It's just one that has a slightly higher age appropriate level than the last one you played," she said as she reached down and picked up the box next to her, placing it on the table. I blinked a couple of times unsure if my eyes were playing tricks on me.

It certainly was a board game. And it was designed for a higher age group. It was for adults. Adults intending to have fun, if you liked your fun naked and it involved some heavy sexual overtones. It was a white box, with a huge red lip print on it in the shape of the letter 'O', like a woman would leave on a napkin in lipstick. Underneath it, in bold red letters, it said, 'The Game of O'. When I saw the box, I looked back at Ann again, trying to read her. And I read yes in her eyes. I just prayed I wasn't wrong.

"Where did you get that?" I asked.

"Gag wedding shower gift," Chad said with a chuckle. "I thought she threw it out."

"I thought about it. But something kept me from doing it. So, do you want to play?"

I shrugged. "That would depend on what exactly it is we're playing. What are the rules?"

"Well, like I said, we can change them if you want. But I can tell you that it's a pretty involved game."

"Involved?"

"Yeah... as in, there will be nudity, and there will be some kind of...."

"Playing," Ann said, as she sipped her wine.

"Intimate playing," Dana said. "But we can do that however you want. I'm not suggesting swinging or anything. I'm suggesting... well, I'm not really sure. We could do this as teams, or... we could just use the cards and the board and kind of make up our own rules."

I smiled and said, "How do you play?"

"It's a normal board game, really. Each player, or like I said, we could do couples... but anyway we each have a piece on the board, and we move it as we roll the dice. And you just follow the instructions on the spot you land on. There are some that make you choose a card, and then you have to do what's on it. I have to be honest, I haven't really read all the rules. I never really thought this box would ever come out of the closet."

"How far does it go?"

"It should only take a couple of hours or so... maybe three," Dana said.

"Not how long... how far?"

"What do you mean?"

"The sex, Dana. How intimate?" I said as I lifted the top of the box and skimmed through the rules printed on the inside. I looked at Ann, who gave me a wondrous look, and I said, "Looks like there's a lot of sex that has to happen to win in this game."

"Yeah... it's pretty...."

"Involved," I said, ending Dana's sentence.

"So... should I put this away?" she asked, almost cringing as she waited for an answer.

Glancing at Ann again, she smiled and mouthed, "It's still Sunday." Her not so subtle reminder that whatever we did, including how far I let us go if we played the game, was totally on my shoulders.

"We'll play," I said, shrugging those shoulders.

"Are you okay with the rules?" Dana asked, trying to contain herself. She was practically coming out of her skin with excitement.

"Well, in reading this, there's no point in playing teams unless we just want to watch each other have sex... and if that's the case, there's no point in getting the game out of the box. We'd have to have a lot more couples to make that an option. But I do have one thing I'm going to say no to right off the start."

"What's that?" Chad asked, taking the box lid from me to glance over the rules himself.

"Ann and I have been down this road before... and while it may seem silly considering all the pictures you've seen, we're are really at a monogamous point right now. And I like it that way, at least for the moment. So, I'm going to say we're up for anything, except for fucking. Oh, and I won't touch Chad."

"Amen, brother," he said, raising his glass as he let out a deep laugh.

"But as girls... we're exempt from the same sex rule? How's that fair?" Dana said.

"I don't have a problem if you decide that's a line you don't want to cross, Dana," I offered.

"What about you, Ann? Is that a line you won't cross?" Dana asked her.

All eyes turned to Ann, who leaned in closer to the table again, her top falling away from her body a little farther than the first time, offering the possibility of a glimpse of the underside of her wonderful tits. While none of us could actually see, I know she had our collective attention. She set down her glass and reached for the board inside the open box, pulling it out and opening it up to place it in the center of the table.

"Well, I'm glad there's no chance of guy-guy stuff. I really don't have any desire to see that... and I know that the guys would both be uncomfortable with it, so where's the fun there," she said as she pulled out the little playing pieces. "Here Neil, you get to be the fat cock. I'm going to be the tight little ass," she said as she put them on the start line.

"You didn't answer my question, Ann," Dana said. "Do you think it's fair that they don't, but we might? Do you want to cross that line, or just cross it off the list?"

She looked directly at Dana; the expression on her face was calm and almost calculated, like she was waiting for the perfect pause. Finally, she smiled and said, "I'm going to do

what I'm made

to do. It's still Sunday."