You Win Some, You Lose Some - Cover

You Win Some, You Lose Some

Copyright© 2022 by Max

Chapter 3

Erotica Sex Story: Chapter 3 - Man hears a woman and her husband discussing wife-sharing. He can't help but put in his two cents

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Fiction   Sharing   Wife Watching   Group Sex   Anal Sex   Oral Sex   Voyeurism  

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Darkness began to fade as the sun made its way toward the horizon. I’d slept fitfully running over ideas and alternatives in an attempt to try to cover all the bases. After only a few hours of sleeping, and more hours of tossing and turning, I finally got out of bed and had room service deliver coffee, donuts and danishes. I had some ideas in mind, but they depended on how Den and Tom had spent their night. I also made a few phone calls to set some things up and to check on others. I could always hope for the best, but I needed to be prepared for the worst as well.

About 8:30, the phone rang. “Hello?” I answered.

“Hey,” Denissa’s voice said in reply.

“Well!” I said with a pleased tone in my voice. “How are you today?”

“We’re ... ummm ... great!” she said. I could hear a smile in her voice and knew that last night had gone well. Maybe better than I could’ve hoped. Time would tell.

“Wonderful. Are you ready for some fun?” I asked.

“Sure,” she replied, “What do you have in mind?”

I grinned into the handset. “Tell you what. Why don’t you and Tom get dressed comfortably, then come up to my suite. We’ll talk things over for a bit and go from there.”

“Ok, we’ll be there in a minute,” she replied.

“See you then,” I said and hung up the phone.

True to their word, in must a couple minutes there was a knock on the door. Opening the door, I smiled as I saw Tom and Denissa finishing a quick kiss. “Come on in folks.” I grinned. “Do you need to borrow the other bedroom for a little while?” I asked. They both blushed a bit, but laughed.

“No,” Tom replied. “Not just yet.”

We collected cups of coffee and Tom collared a donut and two danishes, then went back to the living room and sat in the same places we had the night before. I was pleased to see them sitting very closely together on the couch. “Things must’ve gone well last night” I remarked.

Denissa blushed a little and Tom answered, “I think they went great. We took your advice and enjoyed each other.” Denissa nudged him with her elbow, still blushing.

“You DID enjoy last night, didn’t you ‘Nissa?” I asked her. The blush on her cheeks stayed bright and she replied “Yes.”

Curious as to how well it went, and needing to know so I could gauge what issues I needed to address nest, I leaned forward and said “Sooo... ‘Nissa ... Tell me about it ... Not every little detail, but the highlights.”

She looked at Tom as if asking permission at which point he smiled at her and said “Go ahead, honey.” Looking at her hands, she started telling me of the nights activities About making it in the foyer when the got in the door, then, hesitatingly about the session she had in the bathroom. Tom interjected his viewpoint from time to time, which kept balance and also gave me insights into what he was seeing and feeling, although I was pretty sure I knew how he felt.

The description of the sex session in the bedroom was where ‘Nissa started coming out of her reserved shell a bit. She was talking about the storeroom, and how Hank had finished what he’d started. Her eyes closed as she talked about it and I could tell she was reliving the experience in her mind. Her description got a bit deeper than I think she realized because partway through, she started giving the details. From her point of view.

Tom was listening in rapt attention as she described how rough Hank was. How he’d forced things. How she’d felt as Hank’s hands had touched her. When she was finished, I could sense a slight hint of musk in the air, and Tom had an obvious bulge in his pants from hearing her side of the story. In my opinion, Tom was ready for anything!

But I knew ‘Nissa wasn’t. When she opened her eyes and saw that Tom and I were watching her, waiting for her next words, she clammed up tight. I knew she still had some reservations about something, and I wasn’t sure what it was. She could open up when she was concentrating on the moment, but take her out of that moment and she’d let too many things distract her. I needed her alone for a few hours so I could find her resistance and see if it was something real, or just something that she was afraid of.

I figured the best thing I could do was appeal to Tom. When ‘Nissa went to the bathroom, I asked him “Tom, do you mind if I take ‘Nissa shopping? She and I need to talk about some things, and shopping will take her mind off the main topic.”

Looking hesitant, he replied, “I appreciate everything you’re doing. Last night was some of the most mind-blowing sex I’ve ever had with her, and I know it was because of what we’ve been talking about.” He sighed as he said “But we just can’t afford a big shopping spree right now. It took all the money I could scrape together so we could make this trip.”

He stood up and went to the table for more coffee. “We’ve worked hard to come here and I thought it would be a great way to get her relaxed and then talk about this.” Sitting back down, he had a forlorn expression in his eyes as he murmured, “I just don’t have enough money for her to go shopping.” I almost laughed. “Um, Tom.” I began “Money isn’t an issue or a problem.” Reaching over to the coffee table, I picked up a copy of my latest book and opened it to the flyleaf. His eyes widened when he realized who I was, and he stammered “But, why ... when...”

I did laugh then. “Tom, I want to do this. In a way, it is therapy for me too. And I can certainly afford to spend some money on a beautiful woman.” I smiled ruefully “I’ve not gotten to do that in while. So, if you don’t mind...?”

He smiled back at me, still a little dazzled. “Ok.”

“Ok, what?” ‘Nissa asked as she walked back into the room.

I said to her, “Let’s go shopping.”

She looked a little stunned, then said, “Well, sure. What do you have in mind to shop for?”

“I’m not sure yet,” I replied.

Tom walked over to her, gave her a kiss, then said, “Have fun!”

“You’re not coming?” she asked, a surprised lift in her voice.

I said, “No, I’ve got something for Tom to do.” She looked at Tom, so I said, “Let me grab a couple things from the bedroom, I’ll be right back.”

Ducking out for a moment to give them time to talk, I made some more calls from the bedroom to make some arrangements. I wanted to give them a night to remember, but Tom’s situation was straightforward, so I put the wheels in motion. I also needed some confirmation about ‘Nissa and Tom. I’d had a good feeling that they were OK, but when you’ve made a lot of money, and some of your dirty laundry does hit the newsstands, anything is possible. Receiving the answers I’d basically expected, I hung up the phone and grabbed the essentials that a man has to have (wallet, keys, cell phone, etc... ). Ready to start this little adventure, I went back into the living room to collect Denissa.

She didn’t look terribly happy, but she wasn’t angry either, so I knew Tom had talked her into it. I asked, “You ready to go?”

“Yup,” she said, just a little shortly.

“Good,” I replied. Looking at Tom I stated “Jerome will be here in a little bit. Just relax and let him do his job. He’s the best at it, so just enjoy the ride.”

Tom looked as surprised as Denissa had earlier. I laughed at them and said “C’mon folks. We’re here for fun! Let’s enjoy today. I promise you’ll both get some of those ‘new experiences’ you were looking for.” They both relaxed visibly. “Tom, Jerome should be finished with you around five-fifteen, so just hang around the lobby. We should be there about then.” Denissa kissed Tom as we left.

She was quiet in the elevator, telling me she was a little uncomfortable. I made some offhand remark about the weather to which she replied “Uh-huh.” I knew she wasn’t listening, so I asked her if she knew her shirt was on backwards. “Yeah,” she answered, then realizing what I’d actually asked, she said, “No, it isn’t!”

I grinned as I replied, “Well? You weren’t listening. What were you thinking about?”

She sighed. “Nothing really. I just ... well ... I wonder why you’re doing this? I mean, you had your problems with your wife - ex-wife - about this, and now you want to try to...” she shrugged, unable to really find the words to finish.

“It’s as much for me as it is for you and Tom,” I answered. “In a way, it’s me making sure I know my own feelings about this. So far, everything we’ve talked about is right on the mark. I see you and he and it reminds me of Andy and myself, but I also have learned some hard lessons the last couple years.” I turned her to face me and said, “And, when I find someone I want to be close to again, I want that person to be able to understand me. I want them to understand those lessons. I want them to be comfortable knowing the love that the lessons give is boundless.”

Denissa nodded, knowing some of what I was talking about, but not all of it. If what I was working on panned out, she’d know everything by the end of the night.

The elevator doors opened, and we began to walk across the lobby. I stopped her for a moment so we could talk. Some of what I needed to say to her really needed to be said now, even before we started this excursion. I sat on one of the couches out of the way of the main traffic area, gesturing that she should sit also.

“I’ve made a lot of money, Denissa,” I started “but the old saw is true. Money can’t buy happiness and it doesn’t make you happy. Money is merely a tool.” I leaned back and steepled my fingers, trying to figure out how to say what I needed to say next. “Information is a tool too. And all tools, if used correctly can make beautiful things like the furniture Tom makes.” Denissa nodded understandingly, but not really sure where I was headed with this. I continued, “In order for you to understand Tom and trust his feelings, you’ve got to fully understand yourself. Trust yourself and trust Tom.”

“I do trust Tom,” she said, “but I’m just not sure I trust myself. I’m just not very sure of ... of ... well, of a lot of things.”

I grinned wryly. “Trust is a difficult thing sometimes. Knowing how to trust yourself is even harder. Sometimes it’s easier to do things for others than for yourself. Forgive others. Love others. Be kind to others. So many things we do for others that we can’t do for ourselves without a lot of pain and heartache.”

Leaning close to her I stated, “Before two days ago, you didn’t know me from Adam’s housecat, and could’ve probably cared less. Nor did I know you and Tom. You know some things about me, but not a whole lot other than you feel like my intentions are honorable and kind. I know quite a bit about you and Tom also. Probably more than you’d believe, but some of what I’ve not told you and some of the things I have done I’ve had to do for self-preservation as well as to make sure we’re doing the right things.”

I’d confused her quite well by then, I’m sure. I leaned forward and took her hands “Do you trust me?” I asked, looking closely at her eyes.

‘Nissa stared levelly back at me for a long, hard moment. “You know, night before last I’d have said I didn’t trust any man very much. After Tom said the things he said about wanting to watch me with another man, I didn’t know what to think. But I know you’ve been honest about what you’ve said.” She turned my hands over in hers. “I’ve also always had this gift. I am a very good judge of character. I knew ten minutes into our dinner last night that you were OK. I’ve trusted you with some of the deepest secrets I’ve ever had. Ones I’d never tell even my best girlfriend. So, yes. I trust you.” “I trust you and Tom too” I smiled “maybe a little more than I should. I’m bad to let myself trust too much. And when I do, I sometimes let myself be blinded to things I should see.”

I didn’t really want to tell her the next part. I knew though that if the trust was to be complete, and for this to work it had to be, I had to. “Um ... I’ve learned that I have to be careful about ... people.” I said. “Sometimes that means I have to do things to protect ... myself ... and...”

She could tell I was having problems talking about this. She squeezed my hands and said “C’mon. Just tell me. No beating around the bush. You’ve been honest with us about your relationship with Andy and we’ve been honest too.” I nodded, lowering my eyes “I know, ‘Nissa. And I felt deep inside I could trust you and Tom. But, I had to know so I made some calls to check up on you.”

She was quiet for a moment, and then said “And what did you find?” “What I already knew,” I said. “What I already felt.”

Letting go of my hands, she tilted my face back up to look at her “Then it’s a difference that makes no difference.” She leaned forward and gave me a soft, quick kiss on the lips. “Now. Let’s go. You said you were gonna take me shopping!” she said, grinning.

Standing up, we proceeded out the main doors of the hotel. A long, black stretch limousine I’d ordered earlier was waiting for us to appear so it could shuttle us around town. Denissa looked amazed at how big the car was, and at the doorman who opened the car door for us to enter. “Thanks, Jim” I said. “You’re welcome, sir” he replied.

Denissa looked around at the huge interior of the car, taking in the TV and stereo, the full bar and fridge. She asked, “Where’s the pool?”

I grinned. “That’s in the trunk, but they’ve drained it so we can put packages in it.”

Grinning back, she said, “Does this thing have coffee in it?”

“Nope,” I replied, “but the place we’re going has good coffee.”

She grinned. “I love good coffee. So,” she said, shifting in the leather seat, “where are we going, and what are we shopping for?”

“We’re going shopping for YOU,” I said, “and we’re going to the best place in the world to find it.”

“Riiiiight,” she said, laughing as the limo pulled up front at a very prominent store. I’m sure you’ve heard of it, and no, it’s not Gimball’s. Walking through the doors, Denissa stopped and just looked at the immensity of it. One entire city block devoted to one store. Everything you could ever want was in this store, and I knew it had the world’s best fashion area. I’d told Denissa to dress comfortable knowing she’d be changing clothes for a good chunk of the morning, and maybe part of the afternoon too.

“C’mon,” I said, “you wanted coffee?” We went to the café area and ordered, then sat at a table, talking about the store. I pointed out different areas, having been there several times both for shopping and for signings. I asked her about her clothing preferences, and she indicated she preferred to dress like she was today. Jeans, knit shirt, street shoes or tennis shoes. I asked her what she wore when she dressed up, and she made some remarks about the dress she wore last night. I asked some more questions then I asked “How do you feel about how you look, Denissa?”

She flushed a bit, but said, “I know I’m not the prettiest woman in the world. I guess I look ok, but not spectacular.”

I knew then I’d finally found what was bothering her. She just didn’t have the confidence in her own beauty. She was afraid Tom was pushing her off on someone else, so he could be free. I smiled to myself, shaking my head. I’d seen the same thing so many times it wasn’t even really funny anymore.

Women have this image of themselves that society has imposed which is almost always totally wrong. “I’m too fat. Too thin. My breasts aren’t big enough. Too big. My butt, my thighs, my tummy ... et cetera, ad infinitum. All women are beautiful. I take that back. They can be beautiful, if they let themselves. Accepting who they are and letting that show through changes everything about how a man looks at a woman. Denissa had the physical beauty, but she’d always heard that “this” was better than she was. Maybe as a kid, her brothers picked on her, or guys were afraid to talk to her because she was pretty. Guys actually have more problems with self-confidence than women do, we just exhibit it differently.

“Well, ‘Nissa, we’re going to do things a little differently today. Come on,” I said.

We went to the clothing area, where we picked up a sales clerk. “May I help you find something?” she asked. Denissa had stopped at a book display, and I noticed she’d found my book. Grinning at the clerk, I said “Let’s redo her. Here’s where I want to start, and here’s what I want.” We started with a satin t-shirt dress in blue. Low, strappy heels to match, when Denissa complained about high heels. Didn’t matter which ones the clerk tried, she just didn’t feel comfortable wearing them, because she never had worn them. Since I didn’t want her breaking her neck tonight, we settled on the low heels, but I had the clerk include the high ones in her packages. Hopefully, she’d want to practice.

More shoes, button-up shirts, and button down skirts, we bought her an entire wardrobe of new clothes. ‘Nissa wasn’t completely comfortable with all the selections, but I knew given time after working on her attitude, she’d be happy to have the new clothes.

I had the clerk wrap most of the packages, keeping the t-shirt dress, a light silky jacket and the low heels aside for later. By that time, lunch was in order. We went back to the café where we had coffee earlier, and ordered some light food. Fish for me, a salad for her, and more conversation about Denissa. We talked about her childhood where she confirmed my suspicions about rambunctious brothers and a tom-boy upbringing as she tried to keep up. She asked me about my career and admitted she knew who I was, which caused me to smile.

“So” I asked “now that you know I’m a lazy bum, how do you feel?”

She laughed, giving me a light punch on the arm, “Lazy bum’s don’t have best sellers,” she said.

I grinned back. “But, don’t you know that writing is about the laziest way in the world to make a living? All I have to do is sit at a computer and type some story then hand it to my agent to sell.” She shook her head, smiling “I’ve read your books for years. I like to read them because its always something with meaning. Something that makes a difference to someone. Even when it doesn’t end exactly the way I thought it was going to in the beginning, it always ends well.”

I nodded “That’s what I want to bring to a story.” I took a bite then said, “but each story is different, just like each relationship is different. Some work well, some have problems, some break apart and don’t ever get put back together. You wouldn’t believe how many books I have on my computer that have died and I’ve not gotten back to them to revive them.”

“Really?” she asked.

“Sure,” I replied, “every story doesn’t have an ending. Like the fantasies you and Tom are just now starting to explore.” She got a slightly uncomfortable look on her face so I said, “Let’s do some storytelling of our own.”

Looking interested, she said, “Ok, how?”

I said, “All right. In this story we have several options to look at. Let’s say we’ve got a female main character who’s interested in exploring her sensuality.” I didn’t say sexuality because “sex” has so many negative vibes placed on it by society. Sensuality gives it a softer, smoother meaning, yet the core issues are still there. Denissa nodded, knowing the story was going to be about her, but the detachedness of a fictional character gave her the space to explore it mentally “She has this partner who has told her she can explore whatever she wants, whenever she wants as long as its safe and he knows about it.” I knew Tom had told her that almost word for word. Not because he’d told me he’d said that, but because it was the same words I’d told Andy.

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