My Cuckold Experience with Hailee Steinfeld

I had been dating Hailee Steinfeld now for a little over a year, and well the sex between us was great when the relationship first started, I however couldn’t help but notice that the magic wasn’t really there anymore. In an attempt to spice things up, I suggested that we should discuss whatever sexual fantasies we had, as I figured it could potentially liven things up for us in the bedroom. It was because of that that I confessed to my girlfriend Hailee, telling her how I fantasized about watching her have sexual intercourse with other men.

“Wait what, are you serious,” Haiz began to speak, as I listened to every word, she spoke “…your fantasy is me getting fucked by another guy?”

“It’s really not that surprising,” I explained “…a lot of men have these cuckold tendencies, at least from what I gather online.”

“I’ll be honest with you babe… I know I probably shouldn’t, but I find this fucking hilarious.”

“Geez thanks.”

“Look I’m not saying I will,” Hailee says “…but let’s say I do want too one day, we do things my way, I get to pick the guy as well as both when and where it’ll happen, is that understood?”

“Of course.”

Given that Hailee didn’t bring it up again since the night we had that conversation, I honestly thought she had already made up her mind, and that the answer would be no, so I was taken by surprise a few months later, while we were on vacation down in Hawaii, when the stunning twenty-one year old leaned in, and whispered into my ear…

“I think I’m ready.”

“Ready for what?” I asked her.

“You know, I think I’m ready to make you a cuck.”

“Like right this second?” I said with enthusiasm in my voice.

“Well not like this very second,” the actress stated “…but I definitely think I want to experience another man’s cock, while we are here on vacation, after all that is what you wanted, isn’t it hon?”

“Yeah, of course,” I chimed in “… I would love nothing more than to watch another guy screw your brains out.”

Unfortunately for me, it wasn’t until our third day in beautiful Hawaii, while the both of us were down at the beach, enjoying the scenery, when someone finally caught her attention.

“Oh what about him babe, he looks pretty hot,” the girlfriend says, as she pointed out a guy, who I could instantly tell was taller, and better looking than I was, “…I bet he has a nice big cock, why don’t you go over there and invite him over.”


A moment later, I found myself walking up to the Caucasian male, that Haiz had pointed out, and introduced myself, before inviting him to join Hailee and myself. Once we made our way back towards the famous starlet, the three of us made small talk, as Hailee had me explain the situation to the man whose name we would learn was Dan.

“So are you interested?” I state. “…are you going to come back to our room?”

“How do I know this isn’t some kind of trick?” Dan asks the both of us.

“You don’t, but maybe this will help convince you.” Hailee interrupted.

With that, I watch as Hailee moves towards the man we had just met no more than fifteen minutes ago, as she meets his lips with hers, giving him a kiss that lasts several seconds, before pulling away from him.

“I’ll ask again, do you want to come back to our room, or not?”

“Shit yeah.”

A couple of minutes later, I was following Hailee and Dan from a few feet behind, watching them, while my girlfriend wrapped her arms around his, as the three of us left the beach, making our way back to the room that Haiz and I had rented out. Once inside, before I even had the door fully shut, the two of them wasted little time getting started, as Dan was already helping the “Most Girls” singer out of her two piece pink bikini, exposing the young woman’s now naked body to the cool air.

Hailee Steinfeld grabs Dan by the hand, leading him to the bedroom in all her naked glory, as I couldn’t help but catch his eyes dart down towards her perfect little ass. Once we reached the bedroom, she instructed him to take a seat on the edge of the bed, before grabbing the waistband of Dan’s black shorts and pulling them down to his ankles.

“Damn sweetie even flaccid, he’s bigger than you,” the Edge of Seventeen star claimed, well looking back at me “… I’m going to enjoy this.”

A smirk crossed Dan’s face, as he sat there watching my girlfriend berate the size of my dick, in front of him.

“Go on, and pull it out,” Haiz commented “… don’t be shy.”

Wanting to be a good cuck, I do as I’m asked, letting my bathing suit drop to the floor, before stepping out of them.

As I stood there stroking my man meat, my girlfriend Hailee Steinfeld stuck her tongue out and twirled it around the bulbous of his cock, before slowly moving up and down coating his pecker with her saliva, working Dan over. The girlfriend parted her ruby red lipstick covered lips, taking her new lovers shaft into her waiting mouth, the young starlet then started bobbing her head back and forth, sliding her oral hole over Dan’s candle wick.

Once Dan was hard enough to Hailee’s liking, she pushed him over onto the bed, before straddling his thick shaft, like a lioness pouncing on prey, as Dan’s meat stick started disappearing into her neatly trimmed love mound. With the Los Angeles born actress on his dick, I watched as Dan placed his hands on her sides, as Hailee continued to gyrate her hips in a circular motion, riding his cock.

“Oh God!” cries out Hailee, “…he feels so good inside of me baby.”

I looked on, ferociously pumping my hand over my one eyed monster, trying to rub one out, as the woman I loved was making my cuckold fantasies a reality, and I could tell by the look on her face, that Haiz was enjoying every second of it as well. Hailee placed her hands on Dan’s chest for extra balance, as she persistently bounced up and down, working his pole shaft over with her sex hole, taking every inch of his rock hard cock, deep inside of her.

“Ugh fuck,” the singer of “Love Myself” moans in pleasure “… should have done this sooner.”

Dan just laid there on the bed with a huge smile on his face, as one of, if not the most gorgeous woman he had ever met, relentlessly swiveled back and forth, while he thrust into her snatch with his schlong.

“Damn man, you must be crazy… I mean if I had a chick this hot, I wouldn’t want her to fuck other guy’s.”

“Well lucky for you I am, or you wouldn’t be fucking her right now.”

Watching my girlfriend Hailee, fuck her new lover, got the better of me, as it didn’t take much longer, until I gave my small cock (in comparison to Dan), one last tug as I shot my load making a mess on the hotel bedroom floor. Honestly, neither Dan nor Haiz noticed, as the movie star steadily bucked her hips from side to side enjoying his massive boom stick, as they screwed each other in the cowgirl position, as I watched from a few feet away.

The two of them continued to fuck for another twenty minutes or so, with Dan attacking the starlet’s pussy, plunging into her with one hard thrust after another, as Hailee’s body rocked back and forth on his white snake. Not long after, I knew Dan came inside of my girlfriend, due to the pace of his fucking slowing down, as he slid into Hailee’s sex hole.

As my girlfriend collapsed on top of his naked body, she laid in Dan’s arms, with her leg across him, a moment later, Hailee rolled over onto her back, exposing her well fucked cunt, as I couldn’t help but notice the cum that had seeped out and started running down her thighs. Exhausted and fully satisfied, Hailee Steinfeld flashes a smile my way, before beckoning me over to her, with a wave of a finger.

“Get over here,” Haiz demands, as I make my way over to the bed.

Once I got onto the bed, the songstress insisted that I get between her legs and eat her out, admittedly I was hesitant at first, but I reluctantly agreed as I lowered my head towards her nether regions. As I began probing Hailee Steinfeld’s pussy with my tongue, I tasted the salty bitter flavor that their mixture of cum presented, as I lapped away eating her out.

“So did you enjoy the show, baby?” the actress turned singer asks me, as she pushed my head further into her cum covered cunt.


I continued to explore the dark haired woman’s young love mound, cleaning up the mess Dan left inside of her, as I tried to get as much of their sex juice into my mouth as possible. Over the next several minutes, I licked back and forth, attacking the Pitch Perfect star’s snatch like a man possessed, munching away until the girlfriend had enough and pushed me away, before speaking.

“I assume you’re going to want me to continue sleeping with other people?” the starlet says as she lifts my head up from her clam.

“I sure do.” I answer back.

“Good babe,” Hailee responds with a devilish grin “…cause you’ve got a couple of cute friends, and I wouldn’t mind finding out what they have packing down there, once we get back home.”

“Like who?”

“Well for starters, Shane.”

“But he’s my best friend.”

“I know and I can’t wait to fuck him.”