Dear Diary - My wife, my friend and me.

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My Step-Sister

Diary Entry: Apr 2018

With Sara now firmly established our fourth member and her relationship with Brian growing closer every day, she and I secretly began to work on a role-play scene that we thought might excite our partners. We’d agreed that we wouldn’t give them any details before the night, and only reveal the bare minimum when we had to so that they would discover everything live, as it unfolded.

The germ of our idea was that we were step-brother and step-sister. I would play Mike, the older step-brother and she would play my step-sister Chloe. We would reveal everything on the night. We were both excited about it, and I hoped that whilst watching us, so would Brian and Anne be.

With the introduction of Sara to our group, we had purchased a two-seater sofa to replace one of the armchairs in the lounge. I had hoped that it would act as a viewing platform when the action took place on the main sofa during role-plays. It would allow a couple to watch together and get intimate with each other if they wanted to. It would also be better for when we just chatted or watched a reply of our recorded footage.

Anne had bugged me all week in the lead-up to Saturday, and I’d heard from Sara that Brain had been no better. Needless to say, we both kept our secret safe and we both looked forward to revealing all on the night.

I even managed to resist Anne’s requests for sex when I got home after the pub after my night-out with Brian. I told her that I wanted to save myself, and also, I wanted her so turned on that she would explode when eventually she got into it on Saturday. Needless to say, we both went to sleep that night desperately frustrated.

Anne was on tenterhooks all day, and as the afternoon turned into evening I began to set up the camcorders. We had gradually become more and more sophisticated. I now had four camcorders all linked up to a central mixing desk and controlled remotely. All footage was saved independently, and I could mix it all at a later date. I even had bought some photographic lighting and diffusers to make things a lot easier to see, and we could set the mood a lot better. Anne had helped me to set up the lounge for the start of our play. She was intrigued that it would be played over two locations, and she tried to extract as much as she could from me about the scene.

We were all set. And as we got ready, I watched as Anne slipped into her underwear. I noticed that she had trimmed her pubic hair a little more than she normally did. When I asked her why she’d done it she said that she had become a little self-conscious about her hair. I knew that it was because Sara was shaved. I took her in my arms.

“Honey. I want you to be you. You are not Sara. I don’t want Sara. If you like your hair thicker, or longer, then let it be. I love it. I always have. Please, stop worrying about what the others think. Besides, I think if you asked them they would tell you to be yourself.”

She kissed me and told me that she loved me. It was so hard not to throw her onto the bed and take her right there and then.

When Sara and Brian arrived I could tell that she was a little nervous, as was I. This would be the first time that we were going to play together as the main and only characters. She wore a simple dress, quite plain, which was in keeping with her character. And as we hugged she whispered that she hoped that she’d do well. I assured her that I had confidence in her and that we’d put on a great show.

As was usual, we had a drink, and Anne had prepared some nibbles. We planned to eat later if we felt hungry and weren’t too busy fucking each other. I took Sara aside and we went over our plan one last time as the other two sat on the two-seater and tried to guess what was about to happen. Finally, it was time, and I stood in the middle of the room with Sara at my side.

“Okay, guys. Tonight’s role-play is entitled, ‘My step-sister’.”

I looked as I saw Anne squeeze Brian’s hand and smiled. I began to give an outline of the back-story to our characters. I explained that Michael and Chloe are step-siblings. Chloe’s dad, married Michael’s mother when she was thirteen and Michael seventeen.

They were as close as any brother and sister could be. She loved everything about him. He used to look out for her at school and stick up for her all of the time. He even got into a fight over her when she was fifteen after some of his friends made sexual remarks about her. Michael had always been there for her.

I could tell that as I spoke, Anne, in particular, was turned on. She loved all of the detail, something that I had come to learn about her, the more that we did it. I stepped aside as Sara took over. She took a breath, she was nervous. I slipped my hand into hers as she began to speak.

“We’d regularly see each other in underwear going to and from the bathroom, or in our bedrooms though, as I passed fifteen my body developed and my hormones raged, and I began to occasionally fantasise about him, but was always too afraid to tell him.

When I was sixteen, my father died from a heart attack. A couple of days after he’d died Mike knocked on my bedroom door, and when he came in he saw that I had been crying he held me and stayed with me until I began to fall asleep, I held him, not wanting him to go, he smiled and when he bent to kiss my cheek and I kissed him, on the lips, a full-on kiss.

He was shocked, he commented that I was a good kisser, and telling me that it shouldn’t happen again. I even asked him to put me into bed, but he was smarter than that, he smiled and left. We never spoke of it again.”

She paused and I looked at Anne, she was staring at Sara, she was hooked already. Sara continued.

“Now to the present day, and I am struggling to come to terms with the loss of my husband, Liam who was killed in a road traffic accident. I have one daughter, she lives in the south of England with her boyfriend. It has been over a year and still, I am struggling with my loss.

This weekend sees the arrival of my step-brother Mike, we haven’t seen each other since the funeral. Mike is single, inexplicably, he has never married.”

I hugged her and smiled at the others. Anne looked at me.

“I love all that detail guys! That’s so fantastic. I’m wet already”

I smiled at Brian who nodded towards his crotch, I could see that he was already hard too.

“Okay guys, we are starting.”

I left the room as Sara sat on the sofa and got into her role.

I rang the front doorbell. She got up and opened the lounge door. We hugged and I kissed her gently on the lips, not a sexual kiss, a brotherly kiss.

She led me into the room and kept hold of my hand as we sat on the sofa. Then she flung her arms around my neck and hugged me.

“Oh, Mike. I’ve missed you so much.”

“It’s so good to see you, sis.”

She hugged me tight, “Oh Mike, I’ve missed your hugs.”

We went into a short routine about my trip out to see her. And she told me about how her friends had tried to get her out of the house, but she felt more comfortable staying in.

“Sis. It’s not good that you lock yourself away like this. Liam wouldn’t want you to mope around this place all day. You’re still young. He’d want you to live your life.”

I stroked her neck and she moaned softly.

“Oh, Chloe. You are so tense. Here, let me massage your neck. I remember that you used to like this when we were younger.”

She turned and I began to gently massage my fingers into her neck and her shoulders. She began to moan softly, and, I suspected that not all of it was acting.

“Hmm, that feels nice Mike.”

“Just relax Chloe, you are too tense.”

She relaxed and leaned into me as I gently stroked across her neck. Gently pressing my fingers into her muscles.

I laughed.

“I remember first meeting you. I told my mum that I thought you were a noisy little brat.”

She moaned. “I did have my moments.”

“But how wrong was I? You were the perfect sister.”

She snorted which surprised me.

“What was that?”

She shrugged, “I wasn’t as perfect as you think.”

I stopped massaging her and stared at her as she turned around.

“Oh really? Do tell.” I asked.

She blushed, I wasn’t sure if it was from the play, or if she was aroused.

I reacted to it. “Oh my, look at you, you’re blushing!”

She pushed my arm away.

“Hey, come on now, I’m only teasing, we’re all grown-ups now, nothing can be that embarrassing.” I tried to soothe her.

She turned away, “I used to spy on you.”

I stared at the back of her head, and slowly reached out and turned her to face me.

“I know.”

She gasped and blushed more, “you knew?”

I nodded. She put my hand over her mouth and gasped.


I nodded and told her that I’d seen her the first time when she saw me lying naked on my bed. It was a hot summer, and I had my back to the door and saw her reflection in the mirror.

She gasped, “I remember that! That was the first time I saw you completely naked and your thing!”

I smiled, “It’s called a penis Chloe, or a cock if you wish. We are adults”

She punched my arm, “Hey! Language.”

I hugged her.

“You also spied on me in the shower didn’t you?”

She nodded, “Yes, sometimes you forgot to lock the door.”

I smiled.

“I never forgot to lock the door, Chloe.”

She stared in disbelief, “You mean you did it deliberately?”

I nodded. “Yes. I’d rather that you got your kicks from watching me, than have one of those snotty little brats at school use you for what they could get.”

She leaned back against my side.

“I forgive you.”

I stroked my fingers through her hair and she leaned back against me. She moaned softly as I gently stroked her hair.

“You know all of my friends fancied you don’t you?”

I nodded and told her that I did.

“You should have heard the things that they wanted to do to you.”

I laughed, “Yeah, I know.”

She turned her head, “What do you mean you know?”

I explained that I’d date a couple of her friends, and slept with one.

“Who?” She asked.

“Stacey, but I swore her to secrecy.”

She turned her head away and huffed. I reached around and hugged her.

“Hey, you’re not jealous of her are you?”

“No, of course not!” She snapped.

After a short time, I patted her shoulder.

“I think that it’s time we went to bed.”

She turned around with a glint in her eye and smiled.

“But we’ve only just met.”

I laughed. I glanced at Anne and saw that she and Brian were now laid down on the sofa. And I could see that as she lay against him, he had his hand under her skirt and was playing with her pussy as she stared at us both. I caught her eye and she smiled at me. I knew that she was enjoying it.

“Oh, can’t we stay here for a bit?” She asked.

I smiled and nodded, “I could never say no to you Chloe.”

We lay there for a few moments when I heard her moan softly which was our signal to move upstairs.

“Come on sleepyhead, let’s get you into bed.”

She giggled, “If you insist.

I looked across to Anne and Brian.

“Okay guys a quick break whilst we change location.”

We stood, and Anne and Brian joined us, I turned and asked if there was too much detail or it was too slow? They both said that it was great and Anne loved all the detail.

“I feel like I know them, Paul.”

I smiled at her, “Mike.”

Upstairs I’d put in a single bed in the corner for Anne and Brian and as they lay down I led Sara to our bed.

“I’m too tired to undress, will you help me?” She looked at me with puppy-dog eyes.

I told her to stop being silly, but she held her arms up and kept them there. I sighed and began to unbutton her blouse. With it removed she let her hands drop and I said that she could sleep in her bra. She shook her head.

“No. I can’t.”

She flopped down on the bed and I stared at her.

“Come on now Chloe, stop all this.”

She pretended to be sleeping. I shook her gently.

“Take my skirt off.” She mumbled.

I sighed and reached up and started to unbutton it. Then I pulled the zip down and she lifted her bum off the bed to let me slide it down her thighs and off her legs. I gazed at her white panties, I could see a damp patch in her crotch.

She looked at me.

“My bra?”

I shook my head.

“No. Now come on into bed.”

I made to grab her and she pulled at my arms and I fell onto the bed beside her.

“I need to be cuddled, sleep beside me please.”

I stared at her.

Chloe. Come on, We’re not kids anymore.”

“Please. I promise not to bite.”

She began to tug at my shirt. I tried to stop her but she switched to my pants. This went on for a few seconds, alternating between shirt and pants until I stopped her.

“Okay. Stop. I’ll get in.”

I stood up and slowly undressed. As I slipped my pants off everyone could see that my cock was poking into my boxers. I had a huge tent inside there.

I slipped onto the bed beside her. Not getting inside as we wanted the others to see.

“Thank you,” She said.

I lay beside her and faced her. I let my arm slide across her shoulder.

“Goodnight Chloe.”

She leaned over and kissed me, she lingered and we both moaned, losing a bit of control.

“Mike, cuddle to me please.”

Without waiting she turned around, a clear invitation to spoon her. As I shuffled over and wrapped my arms around her I moaned, I knew that she could feel my cock pressing into her bum.

“Chloe, you’ll be the death of me.”

Almost immediately she wriggled her bum against my erection. Then she reached behind and touched it. I gasped and pulled away.

“Chloe! What are you doing?”

She turned around and faced me.

“What do you think I’m doing Mike?”

I stared at her.

“But Chloe. You’re my sister.”

She sat up and stared back.

“No! I’m your step-sister, there’s a huge difference.”

Sara pouted at me.

“Mike. You’re my step-brother and I love you. But I also want to fuck you. It’s not illegal. So what is it? Don’t you fancy me?”

I stared at her.

“What are you saying? You want to fuck?”

She nodded,

“Yes. And judging by the state of your cock, so do you. So what is it?”

I sighed and lay back, my eyes closed.

She leaned over and traced her fingers across my chest.

“Mike. When we lived at home, did you used to steal my used panties and cum in them?”

My eyes flew open and stared at her.

She smiled at me.

“It’s okay. I knew that it was you.”

I closed my eyes.

“I’m sorry Chloe.”

I felt her fingers slide down my body as she leaned over and kissed me softly. This time, it was a long, lingering kiss, and definitely with sexual overtones.

“For what Mike?”

I was breathing heavier now.

“Because I wanted to do more than just cum in your panties.”

She kissed me again.

“I know. You wanted to cum inside me.”

I moaned as her fingers slid inside of my shorts and wrapped around my hard cock. My eyes opened and I saw that she was staring into them.

“Mike, I want you more than I’ve wanted anyone before, and it is clear that you want me, so why don’t we stop fighting this, and let ourselves have what we want, and what happens, happens.”

I looked at her, my last bit of resistance about to be broken.

“But Chloe”

She looked at me and put a finger on my lips.

“I’m sick of waiting for you Mike. I’ve fought this for too many years. Ever since I first saw you naked I’ve wanted you. I need you to take me now.”

I closed my eyes as I felt her fingers stroke along my hard shaft. She kissed me and I stroked my fingers through her hair as she began to slowly stroke my cock.

”Oh Chloe, I’ve dreamed of this moment ever since we kissed all those years ago.”

She shifted and slid down my body and pulled my boxers from my legs. I felt the air wash across my hard length, and then I gasped as I felt her lips enclose the head of my cock and her tongue probed my tiny pee-hole. I jerked spontaneously and lifted my hips to meet her mouth. I knew that I was so turned on that I would come very quickly, but we also had a plan for that.

I felt her slide her mouth along my shaft and her tongue work hard as she licked all over my hard cock. She sensed that I was about to come and I felt her start to slide her head off my cock. I placed my hand gently on the back of her head and stopped her. She stared up at me, and her eyes bulged as I pushed my cock into her and it filled her mouth. She groaned as I shot the first spurt of cum into her mouth, and as it hit her throat she moaned and swallowed it, just in time for the second spurt that quickly followed. She moaned as my cum slid down her throat as I held her head in place and fucked my cock in and out of her mouth.

I held her in place until I had finished coming. She did gag occasionally but she managed to swallow it all. And as she licked my shaft clean I smiled at her.

“Oh Chloe, that was the best blow-job of my life.”

I pulled her to me and kissed her, I could taste my cum on her lips as I gently laid her down on the bed and knelt at her feet. I gazed up at her and slipped my fingers into the top of her panties and slid them down, she locked her eyes on mine as I slowly pulled them from her legs and threw them on the floor.

I gazed at her pussy, her smooth pussy was topped by an erect clit and her lips were swollen and aroused. I pushed her legs apart and then lay down between her legs and began to flick my tongue gently across the soft skin of her inner thighs as I moved slowly towards her pussy.

Her fingers grabbed at my hair as I got closer and she pulled my mouth onto her pussy. I let my lips slide onto her clit and sucked it into my mouth. She gasped and arched her back as I began licking and rolling her clit between my lips and nibbling it gently in my teeth. She humped her pussy hard against my mouth as she grabbed at my hair, tugging at it, pulling my head hard into her pussy.

“Oh, Mike. That’s it. Lick me. Oh god!”

I worked my lips against her clit then slid my tongue down and along her wet slit and probed inside of her pussy. She thrust her hips up at my mouth as she pleaded with me to fuck her. I ignored her please and continued to lick her slit and nibble on her clit. She cried out and squealed in ecstasy as she fucked her pussy at my mouth. Her fingers tore at my hair. She was getting so close, I could sense it. Her breathing was fast and light, she moaned and gasped. She begged me to make her come.

Finally, I felt her body stiffen. Her thighs gripped my head and locked it against her pussy as she ground it hard against my mouth and she humped at it and cried out as she came hard. Her fingers pulled hard on my hair as she rocked from side to side and I felt her legs tremble as her orgasm ripped through her.

We lay together for a while as her orgasm washed over her and slowly began to pass. As her breathing slowly returned to normal, she released the pressure on my head and let her fingers relax on my hair. Finally, her legs parted and relaxed and I was allowed to pull my mouth from her pussy. I gasped in the air as I began to breathe more easily.

I slid up her body and lay over her. She pulled me against her and kissed me. I moaned as her tongue pushed into my mouth and danced with mine. We both moaned as my hands caressed her body and we lay there, kissing. Finally, I broke off and looked down at her.

“Wow, Chloe. That was something.”

She smiled.

“Yes, Mike. It was. You’re amazing.”

I smiled.

“We’re not done yet.”

She grinned. “I hoped you’d say that.

I slid down her body and once more knelt between her open legs. I stroked my cock, which was once again, hard and leaking pre-cum. I stroked the tip between her wet and puffy lips. She moaned and spread her legs wider. I leaned over her and searched for her entrance. When I found it I placed my cock against it and looked down at her.

With my eyes locked on hers, I pushed forward, slowly, and steadily and I stretched her before slipping side and slowly pushing deep inside of her. She moaned and closed her eyes as she felt me fill her up. Once I was deep inside of her, I lay on her and she hooked her feet behind my thighs and her hands around my back as I began to move in and out of her.

She started to match my rhythm and pushed her pussy up to meet my thrusts as I pushed deep into her. Her fingers stroked my back as I fucked her. And as I fucked her I could feel the difference between her and Anne. Sara’s pussy was a lot tighter than Anne’s. She also moved so differently to Anne, it was very noticeable, but equally as pleasurable. I began to increase the tempo and was soon pounding her pussy for all I was worth. She pushed back as best she could and we were going at it. She was moaning and crying out as I fucked her hard.

A combination of the tightness of her pussy, and my arousal meant that I knew it wouldn’t be long, and it wasn’t. I soon felt the tell-tale signs and I began to jerk and thrust erratically into her. She sensed it and looked into my eyes.

“Oh yes Mike, Give it to me. Give me your cum!”

I stared at her. It was all too much and with one final thrust, I cried out.

“Ahh Yes. I’m coming!”

And I held my cock deep in her as I began to shoot my cum deep into her pussy. She dug her fingers into my back as she felt my cum shoot into her body. She pulled me into her with her feet and held my tight against her as I lay on her and jerked my cock inside of her as spurt after spurt shot out and into her.

As I lay on her panting, her fingers stroked my back. I heard a familiar sound, my wife was having an orgasm, and as we both looked over we saw that Brian had his hand deep inside of her panties and she had her eyes closed and leaned against him. She had just come. I smiled and kissed Sara.

“You were amazing Sara,” I whispered.

She smiled and winked.

“Thank you. That was awesome.”

I slipped from her and turned onto my back and slid my arm around her. We looked over to Anne and Brian who had his arms locked around Anne. I smiled.

“Well, guys. What did you think?”

Anne beamed.

“That was amazing guys. I loved it. The detail was fantastic. That was one of my favourites Sara.”

Sara smiled.

“Thank you, Anne. I don’t know how you did it, but it felt so real.”

They got up and joined us on the bed. Brian slipped his arm around Sara and kissed her.

“You were fantastic honey.”

She smiled and thanked him.

“I can’t wait to watch that back,” Sara said.

Sara looked at Anne.

“What usually happens now?”

I lay on the bed and looked at Sara.

“Well, Sara. Usually, we’d have a rest, but as we are now a four. Maybe you and I should watch Brian and Anne fuck? I mean she’s just come, I am sure she is desperate to feel him inside of her.”

Sara looked at Anne who nodded.

“If you’re okay with that Sara?”

Sara beamed and nodded.

“It’s only fair.”

I took Sara to the single bed whilst Anne and Brian lay down and began to kiss. We watched as he turned her onto her back and began to stroke his hands over her body. Already highly aroused she was immediately moaning and whimpering at his every touch. He was hard, very hard and wasted little time as he slid down her body and parted her legs. She panted and looked down at him. Her eyes begged him to fuck her, her mouth open, gasping in air, wanting him so much.

He leaned over her and guided his huge hard cock towards her opening. I watched her eye bulge, as he slowly pushed first the head, then the rest of his fat cock into her wet pussy. She moaned long and low as he slid into her. Then she pulled her legs up towards her and spread them wider as he began to move slowly inside of her. He pulled back then pushed deep into her, slowly and steadily he worked his cock into her. They built up their rhythm as he fucked her with long deep strokes and she responds with moans and cries of pleasure. Soon she was moving against him. They were very familiar with each other’s movements now, and they knew just how to move and when to move. And as he quickened she responded by meeting his thrusts and she pushed her pussy up at him. She ground herself against his thrusts and was soon panting and moaning as they fucked.

I glanced at Sara who stared at them both. I slipped my hand down her body and over her smooth pussy. My finger slid between her lips, she was soaked. I let my finger slide onto her clit and I began to gently work it as we watched out partners fuck on our bed.

I watched as Brian increased his pace and my wife responded. Her cries increasing in intensity and frequency. She loved it. Each thrust brought more cries from her and he was starting to grunt, which means that he was close. As I watched I worked my finger over Sara’s clit, moving faster and pressing a little harder. I felt her moving against my hand in subconscious movements. She pushed against my hand as I worked her clit.

Anne was beginning to cry out now, squealing in a high-pitched voice as he fucked her deeper. I could see his butt muscles tense, I knew that he was about to come. I worked Sara’s clit faster as I watched as he thrust then arched his back and threw his head back as he cried out and I heard Anne moan.

“Oh god, I’m coming!”

He cried out as he fell on Anne and I knew that he was pumping his cum deep into her. As I watched I felt Sara shudder and her legs clamped around my hand as she had her orgasm as she watched her man come inside my wife. All four of us lay in silence. The room filled with the sounds of Anne and Paul as they recovered from their fuck and of Sara as she had another orgasm and started to recover.

We gathered on the bed and discussed our evening.

“Guys, I get it. Watching Brian have sex with you Anne was amazing. It was so hot. I wasn’t sure if I would be jealous. But I’m not. I mean, if Paul can watch you with Brian, and you can watch me with him, and neither of you feels anything other than love towards each other, then I am sure that I can do it. I don’t feel jealous. I just feel that I have had the best night of my life, so far.”

We agreed that for that evening, we were done. So we had another drink and decided that we’d break with tradition, and as couples, we’d sleep in separate bedrooms. A tradition that we kept up, though not always as the same partner.

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