I Agreed to Let My Best Friend’s Husband Stretch My Tight Puckered Hole

My eyes rolled up into my head as anal joy suffused every cell of my being. The friction, the soreness, the stretch of having my sphincter and rectal cavity split wide open was exhilarating!

I was sitting on the sofa, next to Cindy, enjoying a glass of Pinot Noir and having a good chat with her. We had been friends since school and were very close. Back in high school, Cindy and I had experimented with our sexuality and ended up fucking several times. Eventually, she decided she was straight and I ended up falling in love with a wonderful woman and moved in with her.

That being said, Cindy and I remained good friends. I had been a bridesmaid at her wedding and was godmother to her son.

Our conversation was very frank and about her husband. We had discussed the topic several times over the last few months.

“I’m not sure it’s a good idea. Blair and I have extremely strict rules regarding married people,” I told Cindy.

She had been asking for the same thing for quite some time and my answer had always been the same.

“I don’t see the problem, Kinsley. You and Blair have an open relationship when it comes to sex. Josh wants anal and I hate the idea of anything going up there. You love anal!” Cindy argued with a frustrated sigh.

I shook my head.

“I broke up one marriage already, Cindy. You know that. I would hate myself forever if it caused something bad in yours.”

“You won’t. I promise. I’m not the jealous type and you know it,” she said, desperately. “Can you at least ask Blair for permission?”

Truth was, I was holding something back. I had already asked my wife the last time Cindy had begged me to let her husband fuck me up the ass. She had already said yes.

“I did ask,” I said, in a low voice.

Cindy blinked in surprise.

“What did she say?” she asked after a brief pause.

“She said yes.”

“Please, Kinsley. Say yes. It’s his biggest fantasy and I want to make sure he does it with someone I can trust,” she begged, almost pathetically desperate.

“Why do you say that? Has he said anything about looking to do it with someone else?” I replied in concern.

Cindy bit her lower lip and then nodded slowly.

“He suggested we hire a professional… you know… a call girl.”

It sounded like a decent suggestion. I have never had any problem with working girls. I did it myself for a short time to pay my Uni fees, but for Cindy, it was not an option unless she was really pushed. She did not see call girls the same way I did. It was one secret that I had kept from her, that I had taken money for sex in my late teens and early twenties.

“Would that really be so bad?” I asked, even though I thought I knew what she would say.

“God, yes. I wouldn’t be able to look at him the same. Knowing he had soiled himself with some cheap whore.”

I nodded in understanding and then stood. Picking up my glass of wine, I walked to the large window and looked out at her garden. Cindy followed and stood next to me without saying anything. She knew I was thinking about her proposal.

“Where and when?” I eventually said softly.

“Here. In our bed… and I have to watch,” she replied quickly and then held her breath.

Fuck, she had never mentioned watching before.

“Fine… when?” I said, looking into her large brown eyes.

She met my eyes and gave an apologetic half-smile.

“I hadn’t thought about that… tonight? He should be home by seven.”

I snorted a small laugh at how eager she was to have her husband fuck my ass and get it over and done with.

“Have you considered he might want to do it again?” I asked ruefully.

“That’s why it has to be you.”

My jaw dropped and I blinked twice as I realized what she was saying.

“Exactly how often do you expect me to do it?” I asked with a frown.

She shrugged.

“Until he works this out of his system I guess.”

I didn’t say anything. I was annoyed that she had not explained this expectation earlier.

“You can’t back out now, please.”

Cindy sounded worried and apologetic at the same time. She knew I was a little annoyed.

“I’m not backing out. I said I’ll do it… But I might not do it again… understand?” I said firmly.

“Yes… Yes,” she agreed immediately.

We both looked back out the window and sipped our wine. Out of the corner of my eye, I could see her smirking. She knew me too well and knew that I would do it as often as she asked me to, now that I had agreed.

“You are a bad friend,” I whispered with a scowl.

“That is true, but I’m your best friend,” Cindy giggled back and bumped her shoulder into mine.

It was past seven in the evening. Josh sat at the dining table with Cindy and me. He was used to me coming over often and happily poured me another glass of wine while Cindy cleared the plates.

“Who’s the lucky girl?” he said, gesturing at me, indicating the way I was dressed.

He was aware of my sexual life and often joked about it or asked who I was seeing. I twirled a lock of my ginger hair around my finger as I coyly smiled at him. He was a well-built man with green eyes and sandy-colored hair. Josh was good-looking, muscular, and had a very sexy square jawline with a bit of stubble.

“Maybe it’s your lucky night,” I teased and winked at him.

Shifting on my chair to cross my legs, letting the slit of my dress show off the tops of my black stockings.

Josh laughed and grinned at me.

“If I wasn’t married to this beauty… I’d bang you all night,” he replied and shared a smile with his wife.

He had said things like that before and knew Cindy did not mind. Like she had said, she was rarely jealous, and never considered me a threat. Cindy sauntered over, putting her arms around his neck, and kissed him passionately.

“Kinsley isn’t joking darling. She’s agreed to do that thing I won’t,” she said, looking me in the eyes.

Josh laughed, thinking we were playing with him. I kept my eyes on his as I got to my feet, reached behind my neck, and undid the clasp of my dress. His eyes went wide with shock as the dress slid down my body and pooled around my feet in a soft rustle of falling material. All I had on was the stockings and suspenders, high heels, and my jewelry.

Showing Cindy’s husband my body gave me a thrill. He had never seen me without clothes so he was scanning my nudity. He licked his lips nervously while his eyes flicked from my pale breasts to my shaved slit.

“Holy shit!”

I smiled as I turned to display my butt. I was aware of how great my ass looked when framed by the black suspender belt and black stockings.

“I believe this is what you want,” I said huskily as I bent slightly to give him a good view of my backside, thigh gap, and jeweled butt plug.

Looking over my shoulder., I saw him nod dumbly as Cindy stroked his hair and kissed his cheek.

“This is a gift, honey. Kinsley’s ass is all yours tonight, but you’re not to go near her pussy. Understood?”

Josh shook his head as if to clear it.

“You are being serious, aren’t you?” he asked in a disbelieving tone.

“Well… You’re not putting that monster in my ass and I won’t have you pay for it.”

Josh stood and took both of Cindy’s hands in his.

“Thank you. I love you so much,” he said, looking down into Cindy’s eyes with intense love.

Cindy smiled up at him and then at me.

“Let us go upstairs. Together,” she said softly.

Josh nodded and held out a hand to me. I took it and let him lead me and Cindy up to the bedroom. Their large bed looked inviting and I crawled onto it. I did not look back as I lay my head on the pillow and raised my ass high into the air.

“Are you going to watch?” he asked Cindy as he began to undress.

“It would be weird if I didn’t… don’t you think?” she replied as she sat on the bed and patted my rear.

She rubbed her hand over my asscheeks and then tapped the jewel of my butt plug.

“Yeah,. I guess so,” he said as he got on the bed behind me.

I felt him caress my ass and could imagine the huge grin on his face.

“Your ass is amazing, Kinsley,” he said in an awed whisper as he massaged it and then hooked his fingers under the base of my plug.

I stayed silent as he experimentally tugged on the plug.

“Does that hurt?”

Clearly, a man who had never done any ass-play before.

“No, you can tweak it around a bit…”

I could hear his breathing quicken as he did as I suggested. He twisted the plug inside of me. He seemed fascinated as he pulled it upwards and made my ring bulge a bit before letting go and then doing it again.

“Use a bit of lube, honey,” Cindy said pouring a generous amount of lube onto my ass crack and spreading it around the flared base and around my ring.

Josh then decided he wanted to feel around inside me and pulled the plug out. I moaned as I felt him slide two fingers into my asshole. He went slow at first, exploring with his well-lubricated fingers, delving deeper and deeper until he was knuckle deep and making a circular motion inside me.

“What does it feel like?” asked Cindy.

“Soft. Warm. Tight yet like I could get more in,” Josh answered.

“Not you, silly,” she laughed out as she put her face next to mine and looked into my eyes. “You!”

“Very naughty,” I replied as her husband continued to finger fuck my anus.

“You always were a bit of a dirty slut in school,” she said with a giggle.

I grinned at her and winked.

“Billy Robertson and Steven Daniels,” I replied.

Cindy blushed and glared at me. It had been her who had had the first threesome out of us.

“Who are they?” her husband asked as he played with his fingers inside my asshole, massaging my rectal walls.

“No one you know darling. You know how Kinsley is,” Cindy replied quickly, making it sound like those boys were part of my past and not hers.

“Yeah… and now I’m getting a turn,” her replied excitedly as he removed his fingers and positioned his cock.

I felt the tip push against my back door and let out a gasp of anticipation. Cindy sat up to watch as her husband slid the head of his cock into my ass, stretching it wider than I had expected and making me wince a little.

“Go slow,” I moaned, enjoying the sensation as I relaxed.

His cock was big and thick. Now that my bum hole was snuggly stretched around his shaft. I knew what I was getting.

With both hands on my hips, Josh began to work his cock in a slow rocking motion, easing more and more of it into me. I was tempted to reach for my clit but held back. My pleasure had to be secondary to keep this about Josh and Cindy. I was to be used.

I found myself moaning and blinking in amazement as he fed me his stiff cock. As he pushed his massive erection into my asshole, I realized I realized I rarely had anything that big in my rear.

Josh pressed his hips against my ass and I knew he was all the way inside my hole. Gentle and steady, he pulled halfway out and then pushed back in slowly.

“This feels so good,” he whispered.

“It… it looks so wrong,” Cindy replied, not really talking to either her husband or me.

Short gasps escaped my mouth as Josh began to thrust a bit harder. Hard enough to make soft slapping noises when his hips banged against my asscheeks.

My eyes rolled up into my head as anal joy suffused every cell of my being. The friction, the soreness, the stretch of having my sphincter and rectal cavity split wide open was exhilarating!

Josh immediately set a punishing pace, eager to drill my rectum. My heavy breasts bounced back and forth as he slammed his hips into mine repeatedly.

“Ungh! Ungh! Ungh!”

My moans were punctuated by the squelch of flesh on slick flesh, my pussy gushing so much that it was soaking the bedsheet beneath.

“Oh fuck!” he panted out in pleasure as he worked harder and faster.

His balls swung and slapped against my shaved pussy lips. They would stick there for a split second, glued by my sopping wet cunt.

Cindy watched in silence as her husband pounded my ass in fast relentless strokes. The room filled with the noise of flesh on flesh and my yelps and her husband’s breathy swearing.

“Fuck!” Josh grunted out suddenly as he slammed all the way inside of me and held himself balls deep in my ass.

I felt his cock twitch inside me as he began to ejaculate, filling my anal canal with his semen. His unloading seemed to last forever as his body shook and made my asscheeks tremble.

With a tired sigh of pleasure, Josh pulled out of my ass and used his hands to hold my asscheeks apart. I imagined he was looking into my gaping hole and enjoying the sight of his cum slicking deep within me.

“Cindy, do you wanna see?” he asked in almost childish delight, wanting to show off his work.

I felt Cindy move behind me.

“That is… A bit sick darling,” she said as she peered into my hole.

“I wanna do it again. Can I do it again?” he asked eagerly.

I turned over and looked at them both. Cindy shrugged and looked at me.

“Okay. Let me know when you get it up again,” I said, rolling my eyes.

Josh began to furiously stroke his cock.

“Be ready in a jiffy.”

I wiped the sweat from my brow and shared a look with Cindy. It was going to be a long night and we both knew it.

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