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I was in my late 20s the first time I cuckolded a man. His name was Bradley. As you probably know, ours was a female led relationship. By that point that was the only kind of relationship I was interested in.

I’d read about cuckolding in my adventures on the internet, but it never quite clicked with me. I enjoy sex, but up to that point I’d never been particularly fond of vanilla sex and I hadn’t yet come around to the idea that submitting to a man could be thrilling for me.

Cuckolding Bradley changed that. As you’ll see, I learned that it could be quite pleasurable to submit to a dominant man for a short period of time. The chance to play an entirely different role for a few hours has become something I enjoy quite a bit, and it all began one night in my bed.

Bradley and I were naked. I was on my back with my arms wrapped around him. His head rested against my chest as I caressed him. I love that kind of intimacy with a submissive. I love the sense of ownership I have over him. I love the idea that he feels safe and protected in my arms.

That sense of safety and comfort tends to help a submissive open up. That’s why I used the opportunity to probe a little.

“What do you fantasize about, sweetheart?” I asked. I knew he liked being called sweetheart. He liked terms of affection that were just a little bit feminine.

Bradley cuddled a little bit closer and kissed my breast. I caressed his hair and ran my fingers down his back. I knew he had an answer and I wanted him to feel okay sharing it.

“I fantasize about you having sex with other men,” he replied. “Great sex. The kind of sex that makes your body tremble. The kind of sex you’re still thinking about the next day.”

I’d had sex like that, but it had almost never involved a man penetrating me. It was almost always the other way around, or it involved me riding a submissive’s face for an hour and leaving him completely soaked in my juices.

“What turns you on about it?” I asked.

Bradley ran his fingers over my stomach and I smiled at how good his gentle touch felt. He wasn’t permitted to play with my pussy or my breasts without permission, but he was free to touch other areas of my body while we cuddled.

“I’m not sure I can really put into words what turns me on about it,” he began. “I think a big part of it is knowing that you’re getting something from another man that I can’t give you. I love the idea that someone else would fuck you so much better than I could possibly fuck you. I love the idea that someone else would be allowed to fuck you with far greater frequency than I do.”

Bradley and I had sex occasionally. Most of the submissives I actually dated got to have sex with me from time to time. Penetrative sex is beautiful. It’s a wonderful way to bond with someone. It’s just not my favorite means of having an orgasm.

I’d read enough about cuckolding to understand that Bradley’s desire for it was an extension of his submissiveness and masochism. What he was talking about was the exquisitely pleasurable emotional pain of knowing that I would choose another man to satisfy me with his cock because Bradley wasn’t enough of a man to do it himself.

I was delighted to feel a bit of arousal building between my legs. The more I thought about humiliating Bradley by fucking another man, the more the idea appealed to me.

“Worship my pussy,” I said.

Bradley swiftly moved between my legs and kissed my pussy, as was his custom. His tongue soon found its way inside me before moving to my clit and finding a beautiful rhythm.

“I like that you understand your shortcomings,” I said. “I like that you understand that a submissive man like you can’t possibly hope to fuck a woman like she truly craves.”

Bradley moaned into my cunt as I felt a sense of power move through my body. It was like it suddenly dawned on me that cuckolding Bradley was an entirely new way to dominate him. It struck me as an exceptionally good way of putting him in his place as my submissive, in fact.

“You know I’d find a man with a bigger cock, right?” I asked as Bradley continued to lick my clit.

He looked up and nodded while maintaining his tongue’s contact with my pussy’s pleasure center.

“You know that size really does matter, right?”

Again he nodded. I smiled. I couldn’t help it. I was genuinely having fun teasing him. Bradley didn’t have a small cock, but he wasn’t big either. He was thoroughly average, in fact, and size does matter. A thicker cock in particular feels better.

“Maybe I will fuck another man, Bradley. Maybe I’ll make you watch how good he makes me feel,” I said as I grabbed his head and began to rock my hips. I rubbed my clit on his tongue. I was using him as a sex toy. “Maybe I’ll show you how worthless your cock really is.”

Bradley groaned. His cock wasn’t worthless, but it felt good to say it. Really good, in fact. I smiled, I moaned, and I climaxed on his tongue.

Soon after, I welcomed him back into my embrace. His cock was hard and dripping precum onto my upper thigh. He didn’t touch himself and I certainly wasn’t going to offer him an orgasm. It was his place to experience arousal without release, and Bradley was happy to embrace his place.


I took my time finding someone to cuckold Bradley with. I probably went a little overboard with the vetting process. I wanted to find the right man, though.

It wasn’t just that I was going to cuckold Bradley. It was that I was going to offer myself to someone in a way I wasn’t used to.

I’d made the decision to find a dominant guy. I wasn’t sure how it was going to go, but I wanted to try surrendering myself to someone for an hour or two. The more I thought about it, the more curious I was to see what it was like.

I won’t bore you with the process of finding a guy. Instead, I’m going to skip ahead to the part where I cuckolded Bradley for the first time :)

The guy’s name was Taron. I chose him for the confidence he displayed during our communications, his good looks, his exceptionally fit body, his big cock, and the promise that he would be comfortable dominating me. He’d explained his history as a dom and I even messaged with a few girls that he’d played with. It left me confident that he’d be the man to show me the joys of cuckolding Bradley as I submitted to someone else.

I really like the rituals that almost always accompany dom/sub play, which is why I had Bradley get naked and fall to his knees before Taron arrived at the hotel room I’d booked for the occasion (I was not yet trusting enough to give Taron my home address).

He looked so sweet and submissive. His dick was hard by the time he was naked. There was no question Bradley was excited about the idea of watching someone else fuck me.

Taron and I had agreed ahead of time that the scene would begin the moment he walked through the door and that I could pause it or bring it to an end at any time by using the word “paisley.” Safety is important with these things, after all.

We’d also agreed that while I would have the ultimate say of Bradley’s participation that Taron could offer direction in the name of making it the most satisfying cuckold experience possible. I would step in if it seemed out of bounds. 

I found my heart pounding as Taron’s arrival time neared. I sat on the edge of the bed and watched the clock turn to 7:00. I jumped when Taron knocked on the door. I closed my eyes, took a deep breath, and did my best to open myself to the idea of a complete role reversal from what I was used to with men.

“Hello, sir,” I said as I opened the door. Taron had explained that he preferred to be addressed as “sir” in dom/sub situations. I was more than happy to play along. As I said, I like the ritual of it all.

“Hello, sub,” he said.

I stepped aside and Taron stepped into the room. He’d clearly put in effort to look good. His suit looked freshly pressed and was tailored to fit his gorgeous body. He’d even styled his hair. I was undeniably aroused at the sight of him.

He took my hand and led me towards the bed. We stopped a few feet from where Bradley waited on his knees as Taron’s hands found my waist. He pulled me close and we shared a stunningly sexy kiss. It felt like I had no choice but to let my body melt into his as his hands moved to my lower back.

“Where does a good submissive belong?” Taron asked after the kiss.

I looked into his eyes, smiled, and said, “On her knees, sir,” while falling to my knees in front of him.

“Good girl,” Taron replied as he reached out and softly ran his fingers through my hair.

I was surprised at how easily he took control and how easily I ceded control. It wasn’t until that moment that I realized how thrilling it could be to flip the script and let my submissive side come out to play for a little while.

Taron looked at Bradley and asked, “What do you want?”

“I want you to fuck my girlfriend,” Bradley replied.

Taron looked down at me and asked, “Is that what you want? Do you want me to fuck you while your boyfriend watches?”

“Yes, sir,” I replied. I felt the wetness between my legs as the words left my lips. The situation had quickly shifted from something I was experimenting with to something I desperately wanted. I was thrilled.

“You may take off my pants,” Taron said.

I reached up and moved my fingers over his thighs and crotch – I felt the bulge I was seeking – before carefully undoing Taron’s belt and unbuttoning his pants. I slowly pulled the zipper down and guided his pants to his feet.

Taron was wearing a pair of black boxer briefs that highlighted the size of his semi-hard cock quite nicely. I felt a surprising surge of arousal at the sight of it. I resisted the desire to yank his underwear down so I could see his cock in close up.

Taron gently grabbed a handful of my hair and pulled me closer to his crotch until my face rested against the bulge. I instinctively rubbed my lips, nose, and chin against it. I don’t know what came over me. It just seemed like the right thing to do.

I heard him chuckle as he watched me offer myself to him in that way. “Kiss it,” he said.

I kissed Taron’s bulge through his underwear. I held my lips against it for a few seconds and then moved lower. I heard him groan quietly as I kissed the head. I breathed deeply. I took in his manly scent.

I was unquestionably aroused and sinking into the beautiful submissive place that I’d spent so much of my life guiding men towards. It was really my first time going so deep and it felt spectacularly good, especially since I was being guided by someone that seemed to possess a great deal of skill in the art of dominance.

“Does your girlfriend suck your cock?” Taron asked Bradley.

“No, she doesn’t,” Bradley replied.

Taron gently pulled on my hair and I let him guide my face away from his crotch.

“Do you want to suck my cock?” he asked.

I’d given blowjobs before but they’d never been my favorite way of pleasuring a man. Despite that, I felt a significant desire to offer Taron that kind of pleasure. I wanted to have his cock in my mouth.

“Yes, sir,” I said.

“You may,” he replied.

I slowly pulled down his underwear and revealed a cock that looked bigger in person than it had in pictures. I’m not a size queen or anything, but there is something about seeing a really big dick attached to a hot guy that has an effect on a girl.

In this case, when combined with the efforts he’d already made to put me in a submissive place, all I wanted to do was wrap my lips around it.

I stroked the shaft with both hands and kissed the head. I felt like another being had taken over my body as I did it. I’d honestly never acted in that way towards a cock. It was genuinely worshipful.

I heard Bradley moan from behind me as I finally wrapped my lips around Taron’s cock and blew him. I sucked on the head and worked my tongue over it. I heard him moan too. I was on my knees in a hotel room giving a blowjob and feeling very much like a submissive and it was so much better than I imagined. It felt like a moment of genuine growth for me.

“Do you like watching her suck my cock, cuckold?” Taron asked Bradley.

“I do,” my boyfriend replied.

“I’d like to see her sit on your face while she sucks my cock,” Taron said to Bradley.

I waved Bradley closer. I wanted to make sure he knew I supported Taron’s desire. Bradley quickly got on his back and I moved to straddle his face and let him lick my pussy while I took Taron’s cock into my mouth once more.

“Get her pussy nice and wet for me, cuckold,” Taron said. “I’m quite certain your cock doesn’t fill her like mine is going to. She needs to be soaking wet or it’s going to hurt.”

There was a chance it was going to hurt anyway, at least at first. Taron was remarkably thick. He was thick enough that my jaw had already begun to ache just a few minutes into sucking his cock. I didn’t stop, though. I knew that a submissive doesn’t stop just because she’s uncomfortable. A submissive puts the desires of her dominant above her own. In that moment, I was Taron’s submissive and I genuinely wanted to make him feel good. I didn’t give a damn if my jaw was sore.

“Is she wet, cuckold?” Taron asked.

“She is,” Bradley answered.

Taron pulled his cock from my mouth and tilted my head back. I stared into his eyes as he asked, “Are you ready to get fucked?”

I nodded vigorously and said, “Yes, sir.”

“Good. Strip and get on your hands and knees in the bed. Face your cuckold,” he demanded.

As you might have guessed, I’m not big on doggystyle sex. It’s a far more submissive position for a woman and so I almost always avoid it. In this case, I found it unexpectedly thrilling to be ordered to get on my hands and knees to be taken from behind. It felt right. Taron was the dominant. I was the submissive. If he wanted to take me from behind and use my pussy for his pleasure – I don’t cum from being fucked from behind – then it was his right to do so.

I stripped and got on my hands and knees as instructed. I looked down at Bradley, whose cock was stiff and dripping precum.

“I loved sucking his cock,” I said to my boyfriend. “I loved having his big, beautiful dick in my mouth. I loved the way it stretched my lips. I loved the way it made my jaw sore.”

Bradley’s hand moved towards his cock. He knew better than to masturbate, but he clearly wanted to.

“I don’t enjoy sucking your little dick,” I said. I was going for it. I was running with the moment and playing up the humiliation. I wanted to make Bradley feel like the cuckold he was about to become. I wanted to play my part as his domme. “It brings me no pleasure to have that thing between your legs in my mouth. You know that, though. You also know that I was wet before I sat on your face. You know I was wet just from sucking Taron’s beautiful big cock.”

Bradley nodded from his place on the floor. He nodded in acknowledgment of the fact that I was genuinely wet when I sat on his face. It was the role reversal that made me wet. It was being able to let go enough to submit to a man that was worthy of it.

Taron rolled a condom onto his big cock and moved into the bed behind me. He pushed three fingers into my pussy and I let out a loud moan as I closed my eyes.

“She’s wet for me, cuckold,” Taron said. He fingered me deeper. “Tell me what you want, sub. Tell your boyfriend what you want me to do to you.”

I opened my eyes and looked at Bradley. I looked at my sweet submissive boyfriend on his knees.

“I want you to make my boyfriend a cuckold. I want you to show him how a real man fucks his girlfriend. I want you to show him what he could have if he was a real man with a real man’s cock. I want you to show him how he could have fucked me if he wasn’t a pathetic little submissive beta cuckold,” I said as I held Bradley’s gaze.

I got wetter watching the pain on his face. I watched it turn to arousal. I watched him fight off the urge to masturbate. I was desperate for Taron to push his cock inside me to complete the circle. I wanted him to play his part in humiliating my submissive boyfriend by fucking me from behind.

Moments later, I got my wish. Taron’s cock slipped into my pussy. He felt enormously thick. It did hurt at first, especially when he buried his dick inside me in one deep push. He clearly wasn’t going to be gentle.

“Oh, fuck!” I cried out. “He’s so much bigger than you. He’s so much fucking bigger!”

Taron grabbed a handful of my hair and pulled. My head snapped back. Pain burst from my scalp as Taron pulled with great force while fucking his big cock into my pussy. I was astonished at how it felt like I was taking a fucking from him. I was giving him my cunt for his pleasure. I was not on the receiving end of a pounding designed to make me feel good. It was designed to make my dominant feel good, which in turn filled me with an entirely different kind of pleasure. Each thrust was pushing me deeper into subspace.

“Harder,” I said. “Fuck me harder. Use my pussy. Show him what it’s like when a real man fucks a woman. Show my cuckold while you’re the real man in this room. Show him why you’re the alpha and he’s the little beta bitch.”

Then the most incredible thing happened. I hit a place where the pain became pleasure. I hit a place where enduring the fucking Taron was giving me became enjoying it. I hit a place where I was absolutely certain I was going to cum.

All thoughts drained from my mind in that moment. All that mattered was being a good submissive for my dominant. All that mattered was giving myself over to him. The deeper I went, the closer I got to orgasm.

Taron tightened his grip on my hair. He pulled harder. He fucked me faster. He delivered two painful swats to my ass.

I screamed louder in response. I entered a state of pure submissive pleasure. I closed my eyes and lost myself in getting fucked.

Then I had a stunningly powerful orgasm. I screamed. My body shook. Taron pounded me through all of it.

As I climaxed I fell onto the bed. His cock slipped out of me. I couldn’t hold myself up. I’d basically lost control of my body.

“Thank you,” I whispered.

Taron smiled. “My pleasure,” he said.

He curled up next to me. He pulled my body against his and put his strong arm around me. I felt safe and comfortable. I felt beautifully submissive.

Eventually I reached down and guided his cock into my pussy. I felt such a strong desire to make him cum. I needed him to cum. He began to thrust into me in the spoon position. Every thrust brought with it this beautiful sense of pleasure. It was the thickness. I was being filled over and over. It was so good.

I beckoned Bradley to the side of the bed. He crawled over and looked up at me.

“He’s so good, Bradley. He’s so much better than I thought possible. He’s so much better than you’ve ever been or ever will be. His cock is far superior to yours. Even now, right after he made me cum, I can’t get enough of it. Every thrust is a perfect, pleasurable dream come true. Every thrust makes me feel more like a woman. Every thrust is a reminder of how useless your dick is,” I said.

I offered Bradley my fingers. He wrapped his lips around them. I fucked his mouth as Taron fucked my pussy.

Eventually Taron climaxed in that position. He groaned and I could feel his cock swell. He filled the condom with a huge load. I pulled it off of him and handed it to Bradley to dispose of.

I curled up with Taron again. I felt his softening cock against the back of my thigh. I felt the wetness of his fluids against my skin.

“Do you want me to stay?” he asked as our bodies pressed together.

“I do,” I replied.

“I’d like to make love you,” he said in a soft, surprisingly sensual tone.

I smiled. In that moment, being made love to sounded perfect. I was still in a beautifully submissive place. I wanted to be filled by Taron’s cock. I wanted to feel his body against mine for as long as possible.

“I’d like that,” I said. “I’d like you to spend the night, too.”

“I will,” Taron replied.

Bradley returned and fell to his knees beside the bed once more.

“Taron’s going to spend the night in the bed with me,” I told him. “You can sleep in the chair or on the floor. Please go there now.”

Again Bradley’s face showed a mixture of pleasure and pain. He was being denied, but he enjoyed it. He moved to the chair and curled up in it. Taron wrapped me tighter in his arms.

That was the night I discovered that my submissive side likes to come out when it can blend with my dominant side. I got to humiliate and dominate my submissive as Taron dominated me. It was exquisitely pleasurable.

Next time I’ll tell you about meeting the man that would become my husband.

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