Dear Diary - My wife, my friend and me.

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An Indecent Proposal

After what my wife described as the most realistic and erotic roleplay that we’d ever done, things settled down. Our daughter and her husband were coming to stay for a couple of days, along with our grandson, life was good.

I was busy making plans for our next roleplay, the ‘Indecent Proposal’ scene, the last of our trilogy. And I’d decided that it should take place away from home so I’d booked a room in one of the best hotels in the North West, a suite in fact, and Brain and I worked on the script in the weeks leading up to it. Anne was told the basic outline so that she could provide some spontaneity, but she knew that there wouldn’t be any major surprises in this one.

Diary Entry: Sept 2017: ‘An Indecent Proposal’

Two weeks had passed since our last get together and our daughter arrived for the weekend, along with her husband and our grandson. It was so good to see them all, particularly the little one, he’s growing up so fast, he’s six now and he’s into everything. We see so little of them that when they left after a fantastic weekend, we were both left feeling a little deflated.

We were sat together on the couch on Sunday evening watching the TV when Anne muted the TV and told me that our daughter had commented on how good she looked.

“She said that I had the sparkle back in my eyes.”

I smiled because I had seen that too. Only I knew the reason for that.

“If only she knew.”

My wife blushed a little. I asked what our daughter had said. She turned to me and smiled.

“If I didn’t know you better, I’d say that you were having an affair!”

I was gob-smacked, I asked Anne how she had responded, she said she made a joke, something like.

“Yeah, like I’ve got an affair in me.”

Anne asked her why she had said that, Claire had noticed how Anne was dressed, and that she wore make-up, which was something that she rarely did unless she was going somewhere. Our daughter and Anne had always been very close. But not close enough that she was ready to hear all about how her mum and I live our lives these days. We sat with each other and reflected on a wonderful weekend, with our gorgeous grandson.

I held her in my arms. “Life just doesn’t get any better than this Anne.”

The following weekend, Brian and I went to the pub for our usual couple of pints. We spent a lot of the time chatting about the last roleplay, he too thought it was the best that he’d ever done.

“It was so damn realistic mate, and Anne, what an actress, she really threw herself into it.”

I agreed, he continued.

“I thought you told me that you and she hadn’t had much success at this before.”

I nodded, we hadn’t. But it was clear that the introduction of him had made all the difference. I told him that Anne wanted to do another like that again but we’d have to make sure it wasn’t just a repeat of the first one. We had a good night, the band was half-decent, the crowd lively and we had a couple of more drinks than usual.

As we walked home, he was quiet. I asked him if anything was worrying him. He reminded me that it was coming up to the anniversary of Dianne’s death. I didn’t know what to say, Anne was better at this than I was. I put my arm on his shoulder and squeezed it, it had come around so quickly.

“You know that we are here for you Brian.”

When we got home Anne’s best friend Sara was still there. They usually met up once a month, to catch up on old times and bitch about their men. But Sara got divorced three years ago and now they bitch about men in general. Hers was a classic tale. Her husband left her for his much younger assistant, and of course, it had only lasted a matter of weeks. He had tried to come crawling back but with Anne’s support, she remained strong and now she is single and done with me.

I hugged her, I had been friends with her husband, but could never condone what he did. She knew Brian too. We had all met several times at dinner parties and the like. They hugged, she kissed his cheek and asked him how he was doing. Of course, she and Anne had remembered the upcoming anniversary, in fact, it turned out that they’d been talking about him. When she hugged me and kissed my cheek, I thought that I saw a strange look in her eye.

She stayed for a coffee then left. She never asked about why Brian wasn’t going too, I guessed that Anne had told her about out ‘sleepovers’. I also hoped that she hadn’t told her anything else.

The following morning when Brian had left Anne and I chatted about the anniversary and agreed that we’d have to keep a closed watch on him, I told Anne that I wouldn’t mind if she had to spend more time with him. I think that she’d intended to do so anyway. I looked at her, I was thinking about the look I saw in Sara’s eye’s the night before.

“Honey. What were you and Sara talking about last night?

She said she had no idea what I meant. I told her about the ‘look’ I saw in Sara’s eyes. Eventually, she sighed.

“It’s Brian.”


She explained that Sara has had a crush on Brian for a long time. And they were chatting about him.

“She asked me whether he was ready for a relationship?”

I listened as she said that she had always noticed Brian, and had been the object of her fantasies when she was married. After her divorce, and watching him after Dianne’s death she realised that she had turned her fantasies into feelings. She admitted that she couldn’t get him out of her head, but wasn’t sure that he was ready, or even wanted to have a relationship.

“I’m not sure that this is the time Anne. What with the anniversary coming up.” I said.

“I know. I told her. But she wants us to find out if there would be any chance for her, in the future.”

We chatted about it and decided that we would leave it until after the anniversary, but we would maybe try to set them up on a ‘date’ and see if anything was there between them. After that, we turned our attention to our upcoming roleplay.

The third and final roleplay of the series was happening the coming weekend. Everything was in place and Anne had even been and bought herself a gorgeous black dress for the evening. We picked Brian up early on Saturday morning and headed down the motorway to our hotel. Brian was a little subdued on the drive down. I asked him if he wanted to postpone it? He insisted that he didn’t, and by the time we arrived, he was back to the normal Brian that we both loved.

We had a beautiful suite. A huge bed, a sitting area with a chair and a matching two-seater leather sofa. There was also a large TV and a small coffee table between the chair and sofa. We dropped our bags and freshened up. It was still early, so we decided to go into town and have a look around, and for Anne to do a little shopping.

We had lunch in town and returned around tea-time, we stopped in the bar and had a couple of drinks, I would say to settle the nerves, but Anne was already aroused, she was not nervous at all.

When we had all changed, and he and I had stared at Anne when she emerged from the bathroom looking stunning, I took her arm, and the roleplay began.

“Let’s go, Alice, we don’t want to be late.”

She smiled at me, “okay Ian,” and we left.

In the bar, we found ourselves a table in the corner, and as we sat a waiter came and took our order. As we waited, she slipped her hand into mine and whispered that she feared that she would come as soon as she was touched, she was so turned on.

We were interrupted and looked up, and before us, was Brian, all suited up, he really looked the part. I felt her hand grip mine.

“Hi there, do you mind if I join you, I hate to drink on my own?”

I looked at Anne, she looked nervously at me then nodded.

“Sure, take a seat,” I replied.

He held out a hand to me, “James.”

I shook it, “Ian, and this is my wife Alice.”

She held out her hand, this time she was trembling a little, but from pleasure, I hoped that she’d be able to control it, she did.

“Pleased to meet you both.”

Then Brian and I went into our rehearsed routine, when we spoke about work, I told him that I was a musician struggling to get noticed, and she said that she was a writer. He asked about her writing and she said that it was mainly romance, but she had yet to get any published.

“I may be able to help you with that, I own a publishing company.”

She immediately took an interest and they chatted about that, as they did, I slid my hand under the table and stroked it over her dress, and into her crotch, I saw her eyes glaze a little as they spoke, I pressed my fingers against her pussy through the dress, I swear I could feel the heat coming from it.

He leaned in close, we followed.

“Listen, guys, we’ve had a nice chat here but it’s time to talk business.”

We looked at each other.

“It’s clear that you two need money, and a lot of it to further your careers, am I right?”

We looked at each other then slowly nodded.

“Well, I do own a publishing company, and would look at some of your work, but, I’m no mug, if it’s not good enough I won’t sign you.”

She looked disappointed, her head dropped.

“However, I have an alternative solution to your problem.”

We both looked interested.

“I’ve got a suite here, and, I’d be willing to give you.” he paused, “Thirty-thousand pounds, for one night with your wife.”

He sat back, we both I stared ahead, then we looked at each other.

I shook my head, “no, we can’t.”

She put her hand on my arm.

“Calm down Ian, don’t be too hasty.”

I glared at her, “Are you serious? Are you really considering this? This stranger wants to take you upstairs and FUCK you all night”

I spat the words out under my breath so only we could hear. She nodded.

“I know, but, it’s just one night, and the money Ian, think of the money.”

“If I may interject, I’m not going to FUCK her as you so politely put it. I’m going to make love to her, and if you’re that worried about her, you can watch.”

I sat back in my seat, I looked shocked, she stared at me, her eyes locked onto mine, pleading with me to change my mind. She paused for a moment then looked at him.

“With a condom!”

He shook his head, “no.”

She stared at him.

“Okay, no condom? Fifty-thousand!”

It wasn’t a question it was her final demand.

He smiled, “I knew that you had your price, done.”

He held out his hand, I glared at it, she nudged me in the side.

“Shake the man’s hand and let’s get on with it.”

I stared at her, “you want this?”

She shrugged, “I want the money, and, if I’m going to do it, at least he’s good looking.”

Slowly I reached out and shook his hand.

In the elevator, she whispered in my ear.

“This is so hot!”

I reminded her that she had to stay in character. Inside his room, he put on some soft music, the lights were dimmed and as he poured the drinks, I slipped over and turned on the two camcorders, yes, we had two now to get the best angles. He handed us our drinks, Ann took hers with trembling hands, he put his hands around hers and smiled.

“Relax, I want you to enjoy it too.”

I coughed, “Hey, James! No touching until we get half of the money up front!”

She glared at me, I smiled.

“Just protecting my assets babe,” I raised my glass to her.

He moved to me and I handed him my bank details, it was one of my store rewards cards, but it did the job. He ‘played with’ his mobile for a minute then handed me it back.

“Give it a minute”.

I nodded he looked at me, “mind if I dance with the lady?”

I nodded, “go ahead.”

I wasn’t looking, I was staring at my phone as I ‘checked our bank.’

With the money confirmed I watched as he pulled her close and slid his arms around her back and they danced, she had her arms around him, her head on his chest and the moved slowly in small circles.

“Mmm, you smell so good, Alice.”

She lifted her face up to his, “thank you.”

He lowered his lips onto her and kissed her. I watched as she melted into his arms, their mouths locked as they continued to move back and forth. I could hear her soft moans as his hands caressed her back and slide down over her ass. He pushed his bulge into her, and she looked up at him.

“Oh my, you are a big boy, aren’t you?”

He smiled as he slowly slid the zipper down the back of her dress. He pushed the straps over her arms and slid the dress down to her waist, revealing what I knew, and he didn’t, she was braless. He gasped as her breasts were released and her nipples, so hard, pointed at him. As the dress fell to the floor his hands cupped her breasts, his fingers so delicately caressing them. I couldn’t take my eyes off her face, she was in heaven, he was being so gentle with her. She stepped out of her dress and he guided her slowly towards the bed. When she felt her legs against the bed she stopped and put her hands on his chest and started to unbutton his shirt, I saw the smile spread across his face. Soon she only had his boxers to remove, she knelt and slowly pulled them down to reveal his hard cock, which sprang up to meet her.

The smile that spread across her face was not fake, she genuinely loved seeing that cock. She didn’t touch it, she slowly stood up and wrapped her arms around his neck and kissed him, pressing her pantied crotch against him. He laid her down on the bed and knelt beside her and stared down at her.

“You’re beautiful.”

She looked coy and so sexy. His hands moved down her body and peeled her damp panties from her, he threw them on the floor as he slid beside her and pressed his lips onto hers.

They kissed, their hands exploring each other’s body, he laid half on her, she kept pressing her legs together, a sure sign that she was fighting an orgasm, and he hadn’t even touched her pussy yet. His hands explored her breasts, so soft, tiny movements, his almost feather-light touch bringing gasps and sighs from her with every contact. He fastened his lips onto her breast, and she writhed beneath him as he slid his hand down her body and over her pussy. With the lightest of touches he caressed her lips, teasing her, then moving to her clit he rolled his fingertip around it, pressing gently now and then. Her moans became cries she was very close. I watched as his finger slipped inside of her, she lifted her legs a little to give him access and she pulled his head from her breast and locked her lips onto his and kissed him passionately. Seconds later her body shuddered as she orgasmed hard, her legs clamped his hand in her pussy as she twitched and shook, she turned to face him and buried her head into his neck, her fingers dug into his shoulder as she held him there.

The only sounds in the room were the soft music, and my wife’s panting as her breathing slowly returned to normal. They kissed again, the dialogue seemed to have stopped, but I didn’t care, I was so focussed on the pair of them. She looked him in the eyes.


Was all she said, he smiled and slid a leg across her and pushed her legs apart. Slowly he slid across her and lay between her legs, his lips still locked onto hers, he reached down and lifted his hips up and she raised her knees, put her feet flat on the bed as he guided himself into her wet pussy. She let out a soft moan as he entered her, she reached up and grabbed his neck and pulled him down onto her, they kissed as he began to slowly and gently move his cock in and out of her. I watched as she held him close to her, kissing him, her feet hooked around his legs as she pulled him towards her.

She was enjoying it so much, as was he. And this was so different to our normal stuff, this wasn’t hard fast fucking, this was beautiful, gentle love, and it was amazing. He quickened slightly as they began to move together, his breathing quickened, and her moans were louder and more frequent. He moaned into her mouth as they kissed, almost constantly. I moved position, I could see his cock sliding in and out of her pussy, her wet juices coating his shaft, her pussy looked so stretched, then I noticed the tell-tale signs of his approaching orgasm, his butt cheeks clenched then he sighed and thrust forward and stopped as he emptied himself into my wife. As he did, he buried his face into her neck and moaned.

“Ohhh Dianne, I miss you so.”

I froze, Anne opened her eyes and looked at me as she felt him shudder, was he crying? We locked eyes for a few seconds then, I knew what I had to do, I slowly turned and quietly left the room.

I sat at the bar, my hands cradled a malt whiskey as I replayed what I’d just witnessed upstairs. My thoughts were starting to run away with me again, but I managed to get them under control and rationalise what I’d just seen and slowly I began to understand what had just happened. When I left the bar, I was in a much better place, everything was going to be okay. Stood outside of our room I paused and wondered how I was going to play it, he would be upset, of course, he knew that I’d be thinking the worst. I took a deep breath and entered.

They were both in hotel robes and sat on the sofa, they looked up at me as soon as I entered, he was about to talk when I stopped him.

“You, owe me twenty-five thousand pounds!”

There was a pregnant pause then we all laughed. I sat in a chair opposite them.

“Look, mate, I’m really sorry!

Again, I stopped him.

“Listen it’s fine. I admit I was shocked, but I’ve spent the last thirty minutes rationalising it and I think I’ve got it.”

Anne interrupted, “are you, okay love?”

I smiled and told her that I was fine which seemed to ease some of her tension.

“Brian, that was probably the most beautiful piece of erotica that I have ever witnessed, it was pure unadulterated lovemaking, from two people who love each other very much.”

I could see from the looks on their faces that this wasn’t the route that they thought I’d go down, and Anne began to look worried.

“Now, if you’d called out Anne’s name then we might be having a different conversation here, but you didn’t. Tell me if I’m wrong, and be honest, don’t worry about upsetting Anne, I believe that at some point during that play, during your sex with Anne, it became so real to you that it reminded you of sex with Dianne, and you stopped thinking about Anne, and it was Dianne that you were making love to.”

I watched his face, I had my answer, Anne looked at him.

“Is that true Brian?”

I could tell he didn’t want to admit it, he didn’t want to hurt Anne, but he had to be honest, he nodded his head slowly and turned to look at her.

“I’m sorry Anne.”

She wrapped her arms around him and hugged him.

“Don’t apologise, it’s fine, I understand.”

He looked at her, “you do?”

She nodded, “yes, when Paul left us alone and told us to make love after we’d had anal, remember?”

He nodded.

“Well, during that, I found myself thinking that it was Paul inside me, you did that good of a job.”

She looked at me, I couldn’t help it, I was smiling.

“Brian, I don’t have a problem with that, in fact, I think that if it works for you then I’d be happy to know that you two fuck, she’s Anne, and whenever you are gentle and make love, if she makes you feel like she’s Dianne, then that’s perfect for me.”

He held her hand and looked into her eyes.

“I’m sorry Anne, but it did. You made me feel so good that I for a moment, I thought I was back with Dianne.”

She smiled and kissed him briefly, “I’m glad Brian, anytime.”

I clapped my hands together and got up.

“Who wants another drink? Champagne anyone?”

I picked up the internal phone and ordered room service. As we waited Brian apologised for ruining the roleplay, I put my arms around him.

“Nothing was ruined, tonight was perfect, and I found something important out about you and Anne.”

He looked at me, “what’s that?”

I smiled, “you don’t want to take her away from me.”

He laughed, “no, I don’t, I want her right where she is now, always.”

We decided that we were done for the night, and after finishing off the champagne we got into bed. I lay on my back staring into the darkness as Anne lay across Brian’s arm. I could hear their rhythmic breathing, it was so nice, and peaceful. I thought that they were both asleep and was surprised when Anne turned slowly and slid over to me, she slid her leg across me, settling her thigh on my crotch, her arm on my chest.

“He’s asleep.”

I slipped my arm under her and pulled her into me.

“Hmmm, it was wonderful tonight darling.”

She kissed my chest, “I’m so glad that you are not angry.”

I shook my head, “I’m not, I know he’s going to need you in the coming weeks.”

She nodded, we both knew that it would be a difficult period for him. I felt her press her thigh into my cock.

“You haven’t come tonight darling.”

I nodded, “it’s okay, tonight was a special event.”

All the same, it’s not fair is it.”

I shrugged, “it’s okay, honest.”

Her hand slid under the covers and she wrapped her fingers around my cock, it hardened almost immediately, she giggled quietly.

“I think your cock disagrees.”

I nodded, “I know, but what can we do?” She answered me by sliding under the covers and within seconds she had her lips wrapped around my cock. I stifled a moan, I didn’t want to wake Brian, and, judging by her small movements and expert sucking, neither did she. I slipped my hands under and stroked her hair as she sucked slowly up and down my shaft, teasing the tip with her tongue and squeezing my balls softly. This was turning into one of the most erotic blow-jobs that I’d ever had.

She took her time, and it took longer than usual, but we both knew that I was close, I felt her hand push my legs apart a little as she tried to suck all the cum out of me, then I felt her hand slip under my ass, I wriggled, lifting it and almost gasped out loud as her finger found my asshole, and after a few rotations around the rim, was pressed home, and penetrated my ass a little. It was all too much, I shot my load hard into her mouth and she sucked down every drop, sucking hard and when I was done licking me clean before sliding up and kissing me. I could taste my own cum on her lips, and she tasted wonderful.

“Thank you, love,” I whispered.

She nuzzled into me, “I love you, Paul, never forget that.”

We woke in the morning, and everyone seemed refreshed from the previous evening, we were all naked still, and as I was the last to come out of the bathroom after emptying my bladder Brian was sat on the bed. Anne was laid down, she looked at me.

“Okay guys, last night was awesome, but I came here to get fucked by you both, so how about it guys?”

I looked at her, then Brian.

“Are you sure?” he asked.

She smiled “yes! I’m sure now come on.”

She directed Brian to sit against the headboard, and she spread his legs and began to suck him, I knew what my role was. I jumped onto the bed and lowered her ass before I slid my cock hard into her pussy, and for the next few minutes all three of us were lost in a lust-fuelled frenzy, I fucked her so hard, forcing her forward onto his cock, she gagged several times as my efforts forced his cock deeper into her throat. He came first, filling her mouth with a load of his cum, she drank it all down and then soon followed him, as her fingers worked her clit as I slammed into her pussy. Feeling her pussy contract around my cock as she came was too much and I groaned, held her hips and rammed deep and exploded into her, my cum poured out to fill her and coat her pussy. I pulled out, a string of cum connected my cock and her pussy until it broke and dropped onto her thighs, I sighed, she rolled onto her side, her face beaming, Brian’s cum on her cheek. He looked at us both.

“Now that was some wakeup call!”

Back at home, and alone in our bed we laid in each other’s arms and reminisced about the weekend as I stroked her hair.

“I know that you are going to look after Brian.”

She nodded.

“If that means you want to make love to him, it’s okay, as long as I know.”

She lifted her face to me, “I don’t think that will happen.”

I hugged her, “I know, but I’m saying, if it did, and you told me, then I’d be okay, if he wants, or needs to be with Dianne again, then, it’s okay, even if I’m not around.”

She let her head fall onto my chest again and we fell asleep.

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