My Cuckold Experience 2
With Hailee Steinfeld
Written by TheLW
Codes: MF, Anal, Cuckold
Disclaimer: This FICTIONAL story was written for entertainment purposes only.


It had been a little over a month now, since my girlfriend Hailee Steinfeld, made me a cuckold on our Hawaiian vacation, when she slept with a stranger named Dan. It was during those events, that Hailee told me, she planned on sleeping with my best friend Shane, when we returned to Los Angeles, and true to her words, she did just that, multiple times in fact.

On this afternoon, I found myself at Hailee's place, as she invited me over to help her pick out an outfit for her date, later on in the evening with Shane, which is to say, going over to his place to get fucked. After going through several different lingerie sets, Hailee tried on a matching red pair, that I got for her, not that long ago, it's while Hailee was trying on the lingerie however, when something metallic caught my attention.

“What the hell,” I say to Haiz “ that a butt plug?”

“Oh yeah, Shane insisted that I wear it, the other day,” she nonchalantly states “...he plans on taking me in the ass tonight.”

“Are you fucking serious?”

" I don't know why you're getting mad about it," Hailee answers back "... you're the one that wanted to be made a cuck."

"Oh I don't know, maybe because every time, I would bring it up, you refused to do it."

"Yeah, well Shane managed to convince me, to at least try it," my girlfriend claims as she just shrugs her shoulders "... besides he brought up a good point, as an alpha male, he should be allowed to have the one thing, a cuckold like you can't."

"I'm not happy about this, but I know it's pretty much impossible, to get you to change your mind, when it's already made up," I respond back to the actress, knowing I wasn't going to win this argument.

With that little quarrel out of the way, the two of us went back to looking through her lingerie, including a light brownish/beige colored set, as well as a black set (see pics) which we ultimately settled on.

“Oh by the way, I got you a present,” Hailee tells me, before going over to the nightstand, next to her bed, pulling out a small brown box, and handing it over to me. Wondering what it is, I quickly open it up, and I'm in for a surprise, to find a cock cage, inside of the box.

"You got me a cock cage" I say, puzzled by the gift "...let me guess, you expect me to wear it?"

"I figured you could at least try it," the Pitch Perfect star claims "...just one night, if you don't like it, we can always take it off later."

"I dunno."

"For me, honey," Hailee asks as she leans in, kissing me on the cheek " would really mean a lot."

A few seconds afterwards, I reluctantly agree, as I lower my pants, allowing Haiz to put the device around my cock, and lock it into place, "It's a perfect fit," Hailee Steinfeld excitingly states.

With a cock cage wrapped around my dick, and my girlfriend having picked out the lingerie she planned on wearing for the evening, she puts on the finishing touches of her makeup, before putting on six inch stiletto heels, and grabbing a black robe with a gold design on it, so she can hide her sexy outfit, while I drive her to my best friend's house.

A short drive later, I pulled up into the driveway of Shane's place, getting out of the car, I walked over to Hailee's side, opening the door for her, so she could get out. The two of us, then walked up to the front door, where I wrapped on it, a moment passes by, before Shane opens the door, letting the both of us in.

Once inside, Hailee wastes little time, as she kisses him on the lips, before running her hand over his crotch. "Mmm, I haven't been able to stop thinking about this cock, since the last time you fucked me," the starlet purrs. Eventually Hailee takes a step back, as she takes off her robe, and hands it to me, before doing a little spin, showing off her incredible body to Shane. With that, Shane reaches over, and gives her nice firm ass, a good squeeze, much to the delight of Haiz.

"I'm going to enjoy this," Shane off handedly mentions.

Not wanting to waste anymore time, the three of us went straight to his bedroom, where Hailee had me help her out of the lingerie she was wearing, while Shane undressed himself. Shane would remove the butt plug from her rear end, he then lifted the actress up, and dropped her on the bed, before getting on top of her, and taking Haiz missionary.

While they hooked up a few times, since Hailee and I returned to Los Angeles, this was the first time, that I watched my best friend and girlfriend have sex with one another, and I had to admit, it was pretty hot seeing him enter the "Most Girls" singer for the first time. Given that I’ve never heard Hailee moan as loud as she was right now, Shane was either a great fuck, or the actress/singer was putting on one hell of a show for me, considering just how animated she was.


"Fuck me harder," the movie star cries out.

Hailee had her arms and legs wrapped around his naked body, while pretty much begging him to pound her harder. Likewise, Shane was all over her as well, both sucking and biting on her tits, as well as giving Haiz the occasional kiss on the lips, all the while thrusting into her.

As the two of them continued to fuck each other, Shane persistently attacked her snatch, pulling his prick out and slamming it back Into her, though from the look of pleasure on Hailee's face, I could tell, she was enjoying every second, of having my best friend's dick, inside of her.

"So good," the songstress hisses into his ear.

Shane would continue to fuck my girlfriend in the missionary position for several more minutes, before pulling out of her, and informing Hailee, that he was ready to take her back door... Haiz rolled over on the bed, so she was on her hands and knees, as Shane moved in behind her. Given Hailee had never done anal before, Shane took his time, slowly inserting his schlong into her anus canal, Hailee clenched her teeth, as Shane fed more of his cock past her sphincter.

Watching this wanton action, I couldn't help but feel a bit of jealousy, knowing my best friend was taking my girlfriend's anal cherry, even worse, considering how many times I've asked Hailee to try this, and her always turning me down, I probably needed to accept the fact I would never be buried balls deep inside of her asshole.

"She may be your girlfriend, but right now she's my little slut," Shane said, directing his comment towards me.

It took a few moments, but eventually Hailee was getting used to the sensation of having him inside of her rear end, noticing this, Shane started picking up the pace, with each thrust into her rectum. As Shane steadily plunged into her bunghole, he wrapped a hand around Hailee's long dark hair, gently tugging her head back, so she could look up at him.

"Tell him who owns your ass," grunted Shane.

“I love you baby, but you'll never fuck this ass,” Hailee pants “...cause it belongs to your best friend.”

“You hear that buddy,” Shane taunts me “... I own your girls ass.”

All I wanted to do was grab my cock, and rub one out, but I couldn't even do that, due to the cock cage that was covering my dick, instead I just stood there, as Hailee's lover vigorously slid in and out of her backside, pleasuring her in ways, she never knew were possible until tonight. My best friend repeatedly pumped back and forth, as he continuously fucked Hailee's asshole, even occasionally smacking her butt cheeks, every now and then, as he intensely hammered into her, one hard thrust at a time.

As Shane's cock started to throb inside of Haiz's bunghole, I watched as he pulled out of her, just as a string of cum, shot out of his boomstick, coating her lower back, and ass cheeks with his man custard. After a moment, Hailee told me to say thanks to my best friend, for being man enough to fuck her in the back door, unlike a pathetic cuck like me.

"Thanks for fucking Hailee," I told him.

"No problem," he responded back "...besides, I'm more than happy to satisfy her sexual needs."

Hailee then got off of the bed, telling me that I should probably head out, as she was going to stay and have a shower with Shane, maybe even go another round with her lover afterwards.

The End