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Mother In Law, Sister In Law & My Wife: Sister In Law's First Anal

Mature Women / Cougars / MILF Stories (Written By MEN)

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Old 10-20-2011, 10:35 AM   #1
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Join Date: Jun 2010
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Smile Mother In Law, Sister In Law & My Wife: Sister In Law's First Anal

Last Saturday, K (sister in law) mentioned to my wife that she'd not seen their mother (S, my mother in law) for a few weeks.

"Why don't you go round to see her then?" asked my wife.
"Will you drive me round to see her tomorrow?" K asked me.
"Of course I will. Ring her first to check it's okay to go round. She might have plans." I replied.

K went into the kitchen and gave S a ring. A couple of minutes later, she came back into the living room.

"Yeah, it's fine. Will you drive me round tomorrow, around 11am?" asked K.
"No problem. I've got nothing else on. Are you going too?" I asked my wife.
"I can't go tomorrow. I've got that health and safety report to finish before Monday's meeting. I'll have my head in it all day." replied my wife.

Running a little late, K and I set off for S's apartment around 11:30am. Nothing was planned for when we got there except a few cups of tea and a catch-up. No sex. Although, having said that, just because it wasn't mentioned doesn't mean it couldn't happen. But, like I said, it wasn't planned. We arrived about 10 minutes later. S answered the door and in we went. S was dressed for Sunday relaxation. A burgundy, long-sleeved t-shirt hugged her curves while a pair of grey pyjama bottoms fit around her arse nicely.

S put the kettle on and made us a cup of tea each. K and I sat on the settee while S sat on the chair opposite. S has gotten herself a nice modern apartment with a balcony. She's done really well. We drank our teas and chatted.

"So, are you still having fun together?" S asked us.
"Yeah, all the time. We've not had everybody round for a while though." K replied.
"If you do organise something, will you let me know?" asked S.
"Of course we will. Don't be daft." replied K.
S smiled, "Thanks. Would you like another cup of tea?"
"Yes, please." answered K and I.

S got up and went to the kitchen. A few seconds later, she came back.

"I forgot that I used the last of the milk." said S.
"I'll go down to the shop if you want?" asked K.
"Would you mind? I'd go but I'm not dressed to go out." replied S.
"I'll go, if you want?" I asked K.
"No, it's alright. I'll see you in a few minutes." K replied.

The door shut behind K and S came and sat down on the settee.

"We could be quick." S said to me.
"With what?" I asked, for some reason.

A split second later, I realised what she meant. But before I could say anything, S pulled down her pyjama bottoms a little. Enough so I could see a nice, unshaven, triangle of hair. There was no fighting it. My dick jerked to life inside my jeans. I quickly stood up and furiously unfastened my jeans. S also stood up and dropped her pyjama bottoms to her ankles. She stepped out of them and kicked them away. As I pulled my jeans off, S assumed the doggy position on the carpet. We both left our tops on as it was only going to be a quick one. I got on my knees behind her gorgeous, round arse. I took hold of my rock hard dick and guided it to her pussy. As the head of my dick pressed against her pussy, I felt how hot she was. My dick slid in with ease thanks to her heavy natural lubrication. I pushed it in all the way.

"God, I've missed having you inside me." S whispered.
"I've missed being inside you." I said.

I moved in and out and a nice speed. S was seriously wet and gasping with every one of my thrusts. Her arse slapped against me. It was an experience that I'd greatly missed. I watched as my dick slid in and out just below her arse. I took hold of her arse cheeks for leverage. In doing this, I gently spread her cheeks apart a little. This revealed her gorgeous arse hole to me. As I stared down at her arse...

"I'm cumming!" shouted S.

We'd only been going for a couple of minutes but S was extremely turned on and I felt her pussy get wetter as she moaned and groaned the orgasm out of her body.

I was just about to pick up the speed a little so I could cum when…

“Didn’t think you’d be able to help yourselves.” K laughed.

S and I both turned to find K stood there, watching us. I stopped thrusting.

“I thought you went to the shop?” asked S, breathless.
“I put the door on the catch, waited a few seconds and came back in. Wanted to see if the pair of you would start having sex. I’ve been watching since he entered you.” K replied.
“You’re not mad though, are you?” S asked.
“Don’t be daft! Why would I be? You know I love it. It was just to see. If I was mad I wouldn’t have stood there watching and getting wet.” K replied.
“Are you going to take your clothes off then?” asked S.

K responded by unbuttoning her jeans. In less than a minute, she was naked. S and I removed our tops. I was still inside S at this point. S slowly began to move back and forth on my dick. She was still soaking wet. K sat on the settee and watched for a few seconds. She looked like she was thinking as she watched.

“Will you let him put it up your bum?” K asked S.
S, still on all fours and sliding on my dick, turned her head towards K.

“If he’s lucky, I might do.” Said S, looking over her shoulder at me and smiling.
“No, I mean can you let him so I can see? I’ve been thinking of trying it.” K said.

S stopped sliding on my dick. We both looked at her, surprised.

“Since when?” I asked.
“For a while. When you cum on my bum hole it really turns me on. And, when I was on my own last week, I fingered it. I really enjoyed it.” K replied.
“Get the lube from the drawer in my bedside cabinet.” S said to K.

K went to S’s bedroom and S slid off of my dick. K returned a few seconds later with a bottle of lube. She handed it to S. S, K and I were both kneeling on the carpet. My dick was still rock hard as I knew what was coming.

“You kept it quiet.” I said to K, laughing.
“I just wanted to speak to Mum first because she has it up the bum all the time.” Said K.

S put some lube into her hand and then rubbed it onto my dick. She then handed me the bottle and assumed the doggy position again. I rubbed some lube on to her arse hole, slipping a finger in and then out again. I put the bottle to one side. K was kneeling next to me and so close that her breasts where touching me. She wanted to see it all happen. Once again, I took hold of my dick and guided it towards her arse. My dick parted the crack of her arse and pressed onto her beautiful hole. It opened up and swallowed the head of my dick. I continued to push and her arse continued to swallow. S was taking deep breaths as more and more of my dick filled her arse. I got all the way in. After a few seconds, I began to slide in and out nice and slowly. K watched as my dick slid in and out of her mother’s arse in a beautifully smooth motion. After only being inside S’s arse for about two minutes, K said…

“Can I try it now?”
“If you want to.” S replied, breathlessly.
“Can we go to your bedroom though? I don’t want to do it on the floor.” Asked K.
“We can go wherever you want.” Replied S.
“Let’s go then.” Said K.

I slid out of S’s arse and we all stood up and S led us to her bedroom. We all got onto S’s double bed.

“Shall I do it doggy style?” asked K.
“Do it how ever you want.” Replied S.
“I’ll do it doggy style.” Said K.

S handed the bottle of lube to K. K put quite a substantial amount of lube into her hand and then rubbed it all over my dick. She then gave me the bottle and got on all fours.
“Will you put some on me?” K asked.

I rubbed quite a bit of lube onto her arse hole, seeing as it was her first time, and then cast the bottle aside. Kneeling behind her on the bed, my dick and her arse hole dripping with lube…

“Are you ready?” I asked.
“Yeah. Go slow though.” K replied, quietly.

The moment I’d been waiting for was finally here. I get to put my dick inside K’s arse. Something that I’d dreamt about for a long time. Her lovely tanned arse presented itself to me. Her lovely pink arse hole waited to receive my dick. I guided my dick to her beautiful pink hole. Pressing the head of my dick against it, it was tight. After a bit of manipulating, it began to give slightly. Slowly but surely, it began to open up. I got the head of my dick in and then stopped. K’s hands we gripping the duvet.

“Are you ok?” I asked.
“Yeah.” K whispered in response.
“Just let him in gently, K. It’ll be alright once he’s in.” S said, comfortingly.

I continued to slowly disappear inside K, millimetre by millimetre, until half of my nine inches was inside her arse. She was incredibly tight. I stopped again.

“I’m going to start moving in and out now, ok? Nice and slowly.” I said to K.
“Ok.” K whispered.

I slid out and back in again, nice and slowly. Loud gasps from K accompanied my every movement. But she was so tight. Her arse hole gripped me tightly. I hadn’t started moving in and out for more than 30 seconds when I knew that I was about to cum. I stopped.

“You’re really tight. I’m ready to cum.” I said to K.
“Not yet. Please?” K whispered to me.

I waited for a minute and then started to slowly move again. But she was still so tight and I felt ready to cum again almost immediately.

“I’m seriously going to cum. I can’t hold it back if I carry on.” I said.
“I don’t want you to cum in me yet. It was only just starting to feel nice.” K said to me.
“Move over a bit then.” S said to K.

I slowly slid out of K and she shuffled from the middle of the bed to one side of it. S got on the bed on all fours right next to K, who was also still on all fours.

“Cum in me then you can be inside K for longer.” Said S.
“That’s a good idea.” Said K.

I didn’t waste any time and entered S’s arse for the second time that day. I moved in and out with ease as S’s arse hole formed a beautiful O shape around my dick. After a short minute, I was firing my cum deep inside it.

I slid out of S’s arse. S got off of the bed and left the room, presumably to go to the toilet. My dick relaxed into a semi-hard on and K moved to lay on her back on the bed.

“Just give me a couple of minutes.” I said to K.
“Ok.” K replied.

K lay there with her legs open a little. Her beautiful pink pussy lips were begging to be parted by my dick. But it was her arse that wanted me today and it was going to get it. S returned to the bedroom a couple of minutes later. She got on the bed and instantly took my dick in her mouth. She licked and sucked it clean and I was soon fully hard again.

“I’ll leave you two to it.” S said as she stopped sucking on my dick.
“Are you sure?” asked K.
“Yes. You should have this time to yourselves.” Replied S.

S left the bedroom and shut the door behind her. Now it was just K and I, alone. I was still kneeling on the bed. K got up and kissed me for a few seconds. Our tongues met and wrestled as K took hold of my dick and slowly rubbed it. After a few seconds, she assumed the doggy position again.

“Put some lube on me.” Said K.

I grabbed the lube and squeezed it on to her arse hole. She jumped a little and laughed as it landed on her beautiful tight hole.

“It’s cold.” She laughed.

It rubbed it on her hole whilst taking in her gorgeous blemish free arse. Once she was nicely lubed up, I rubbed a generous helping on to my dick. Then, we were ready.

“Are you ready for me to put it in?” I asked.
“Yeah, be gentle.” K said, looking over her shoulder at me.
“Don’t worry, I will be.” I answered.

Once again, I guided my dick to her beautiful arse hole. After a bit of a struggle again, it eased in. Her tight, pink hole stretched around my dick as it got deeper and deeper into her arse. I got half my length in again and I stopped. K looked over her shoulder at me.

“Keep going.” She whispered.
“Are you sure?” I asked.
“Yeah.” K whispered in reply.

I slowly eased myself in deeper until I was three quarters of my 9 inch length inside her arse. It gripped my dick with a passion. K took a deep breath as I began to slowly move in and out of her beautiful arse. Her hands gripped the duvet cover once again.

“Are you ok?” I asked.
“Yeah. It hurts a little bit but it feels amazing. Keep going.” K answered.

I followed orders and kept going. After a while it got easier to slide in and out and I was able to gently make love to K anally. It was so hot and tight in there. We stayed in the doggy position as K seemed to really like it. I slowly fucked her arse for a good twenty minutes until I felt the first twinges of an orgasm build-up.

“Where do you want me to cum?” I asked K.
“Are you going to cum?” K asked in a whisper.
“In a minute, yes.” I answered.
“I’d like you to cum in my bum, if that’s ok?” K asked.
“If you’re sure.” I answered.
“Cum in my bum.” Said K.

With that, I continued to slowly slide in and out of K’s arse. K, after knowing that I was close to cumming, began to move back and forth on my dick as I moved in and out of her. This sped up my orgasm and I grabbed hold of her hips as I began to cum inside her beautiful arse.

“Oh God, I can feel your cum.” Said K as my cum shot into her arse.

Eventually, I stopped cumming. I slowly slid out of her arse and her hole closed tightly as I fully withdrew. K collapsed on to her back and I lay next to her.

“Oh, that was amazing.” K whispered.
“It certainly was.” I said.

K and I lay on our sides, the front of our bodies pressing together as we shared a deep and passionate kiss. A couple of minutes passed and K got up to go to the toilet. She came back after a few minutes.

“I think it’s all come out. There was loads of it.” K said, referring to my cum in her arse.

We got dressed and went into the living room, where S was.

“Did you enjoy yourselves?” S asked us.
“Definitely.” I replied.
“I loved it.” Replied K.

We talked a bit longer and then K and I got into the car for the short drive home. In the car, K asked me if I’d have sex with her again later on. No anal, just the ‘usual’ way. I happily obliged and we enjoyed ourselves later on in the evening. At the time of writing this, I haven’t had anal sex with K since. No because she doesn’t want to, it’s just because she doesn’t want us to do it all the time, so when we do actually do it it’ll be fantastic. I, for one, can’t wait.
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Old 07-25-2012, 07:13 PM   #2
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Join Date: May 2009
Posts: 45

you are one lucky man. what was the reaction from your wife when you told her that you and her sister had anal sex?
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anal, ass, cum, milf, pussy

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