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Henry was bent over the balcony of our hotel room on Grand Cayman. We’d booked a vacation to celebrate our one year anniversary and we’d splurged on a particularly nice room on the 16th floor.

He was looking out at the ocean as I approached from behind. He looked back and his eyes wandered to the red strapon cock I’d just put on.

“Did you enjoy watching?” I asked. A particularly fit young man had spent the previous half hour offering me a vigorous fucking and Henry had watched it all while locked in the chastity cage I’d put on him the moment we landed.

“I did,” Henry said as he stood up.

“No, no,” I said. “Stay like that. You look good bent over like that. You look fuckable like that.”

Henry knew what was coming. I didn’t change into the strapon just to model it for him. I’d promised him a reward after my young lover left and for a submissive there’s pleasure to be found in getting fucked by your girlfriend’s cock.

I stepped out onto the balcony and admired the view – and the total privacy we enjoyed out there – and ran my fingers down Henry’s back. I reached out and played with his caged cock and the precum dripping from the tip.

“He fucked me hard, didn’t he?” I asked.

Henry moaned as I teased him through the cage. “He did.”

“He was quite large too, wasn’t he?” I asked. I’m fairly certain the young man was sporting ten inches of cock between his legs and it was remarkably thick, too.

“He was,” Henry said.

I ran my fingers between Henry’s cheeks and teased his asshole. “Did you enjoy watching him make me cum?”

“I did,” he answered.

The first few times I cuckolded Henry I wasn’t entirely sure he enjoyed watching. I think he liked that I was having great sex and I think he liked knowing that I would reward him afterwards, but it was always hard to tell if he was genuinely enjoying himself. By the time our one year anniversary rolled around I was convinced of it, though. I hadn’t cuckolded him dozens of times – I like a good fucking, but I also like having sex with Henry – but it had happened often enough that he’d gotten used to the idea. I think he liked that I typically found a new way to reward him each time.

“Did you think you’d get to fuck me on our vacation, Henry?” I asked.

“Yes,” he answered.

I spit on my fingers and rubbed them over his asshole before working one inside him. I slowly penetrated my boyfriend and smiled as he groaned.

“Did you think I’d fuck you on our vacation?” I asked.

“I thought you might,” he said.

I slipped a second finger inside him and started to fuck his tight ass as his moans got louder. There’s something so hot about a man bending over for you and taking it in the ass. It’s even hotter when you’ve got a strapon cock protruding from your pelvis that you’re itching to pound him with.

“Do you want me to fuck you?” I asked. “Do you want me to give you my cock? Do you want me to pound this tight little ass of yours while you’re bent over the balcony?”

Sometimes all it takes is a good round of dirty talk to drive me absolutely wild. I’m telling you, it’s incredible. In that moment I’d just come off getting fucked to a place of the purest pleasure by a gorgeous young man and I was already hot again as I penetrated my boyfriend’s ass to prep him for my strapon.

“Yes,” Henry said. “Please, fuck me. Take me from behind. Take my ass.”

I spit in my hand and stroked my cock, which I can’t get enough of. There’s something so hot about that view, about the sight of my hand moving up and down my cock that makes me love strapon sex.

I placed a hand on Henry’s lower back and gently pressed the tip of the strapon against his asshole. He groaned as it slipped inside and I felt that rush of dominant pleasure as I watched it fill him.

I leaned down and wrapped my arms around Henry with my cock buried inside him. I kissed his back and let him feel my breasts against his body.

“I love you,” I whispered.

“I love you too,” he said.

I felt an overwhelming desire to contrast that moment of tenderness with something dominant, so I stood up, grabbed a handful of Henry’s hair and pulled back hard as I began to pound him. He cried out in what seemed to be a mixture of pain and surprise, but soon enough he was moaning.

I felt like a dominant goddess in that moment. I had my boyfriend bent over a balcony and I was admiring a beautiful ocean view as I fucked his ass with my strapon. I filled him with long, deep strokes and he grunted and groaned like a bitch (that’s a good thing). It was fucking incredible and I can’t even explain to you how hot the whole thing made me.

“Take it,” I hissed between hard thrusts. “Take it in the ass. Take it like a slut.”

I surrendered to the part of me that likes to get aggressive when I dominate Henry. It was hard not to. I wanted to own him in that moment. I wanted my cock to own him. I wanted to completely and utterly dominate him and I really did. I could actually feel him give his body over to it. He was a vessel for my pleasure in that moment and he was fully enmeshed in it.

I laid into him for a good five minutes, which is a lot longer than it might seem. That’s five minutes of steady anal pounding. That’s five minutes of hair pulling, ass spanking, and verbal humiliation.

I felt like I was high as a kite when I pulled out. My whole body hummed with desire and I wanted to give Henry his reward, as taking a vigorous ass fucking isn’t really a reward. I stood him up, spun him around, and unlocked his cock. I took him in my mouth and looked up to see absolute joy on his face as I blew him. I sucked Henry’s cock until he was stiff in my mouth and then stood up and kissed him. I stroked his shaft and he groaned into my mouth.

“Would you like to be inside me, Henry? Would you like to fuck your girlfriend?” I asked.

“Yes,” he said.

I took Henry to the bed and pushed him onto his back. He had this adorable look on his face as I straddled him. He was like a puppy about to receive a reward. He was overcome with excitement at the idea of being inside me.

I sat on Henry’s cock and watched his face as the pleasure of being in my wet pussy hit him. He groaned, closed his eyes, and smiled while I took him for a slow, sensual ride.

“Does that feel good?” I asked.

Henry opened his eyes, smiled at me for a moment, and said, “It feels perfect. Nothing has ever felt better than this feels.”

I leaned down and we shared a long kiss as I rode Henry a little faster. The pleasure building between my legs was fantastic and I wanted more. I couldn’t help but want it to feel a little bit kinky, to be honest. I knew it was a risk, but I wanted to keep dominating Henry.

So, I took a chance. I kissed him. I kissed his neck. I nibbled on his ear lobe. I rode him a little faster and he moaned. Then, I whispered, “His cock felt better inside me.”

Henry grabbed my ass and moaned. He fucked his cock up into me, trying to wrest some of the control. I let him have it and offered more verbal play. “Do you like that, Henry? Do you like that another man fucked me better than you’re fucking me right now?”

Henry moaned louder. He squeezed my ass harder. He tried to fuck his cock up into me harder and faster. I kissed his neck and moaned for him. I moaned like a pornstar, though mostly because it felt really good.

“Fuck,” Henry said. “I’m close.”

“He fucked me better than you, Henry,” I said. “He fucked me better than you, but you get to cum inside me. You get to cum inside me and then you get to clean up your mess. You get to clean your sticky mess out of me like a good submissive cuckold should.”

I could have cum, but I held off. I wanted to have my orgasm while Henry was eating his load from my pussy. Something about that felt so much sexier. Henry came, though. He came hard. I watched his face. It was beautiful. Watching me get fucked and then taking a toy in the ass seemed to put him in a place of insane desire, leading to a much better orgasm.

He still had a smile on his face when I pulled my pussy from his cock and sat on his mouth. “Clean me,” I said. “Eat your load and make me cum.”

Henry grabbed my ass with two hands and went to work. He cleaned me like a good cuckold should. He cleaned every drop of his load and he got me off in the process, just like I wanted.


“I’m impressed,” I said as Henry slowed the boat we’d rented and dropped anchor in a safe spot.

He turned to me and smiled. “My parents owned a boat when I was growing up. They still do, I guess, I just haven’t been on it in years. It’s not quite as simple as riding a bike, but you don’t really forget how to operate these things.”

We’d rented the boat for a snorkeling trip and Henry had guided us towards a secluded spot just off the coast with ease.

“Well, I’m still very impressed,” I said as I stood up and pressed my bikini-clad body into his before we kissed. I figured I’d go for it so I offered a long kiss with plenty of tongue and much to my delight Henry’s cock sprang to life, creating a lovely tent in the front of his swimsuit.

“I should try to impress you more often if that’s the kind of reward I get,” he said with a smile.

I gave him another quick kiss and said, “Let’s go snorkeling.”

We geared up and hopped in the water for what ended up being a truly memorable experience. The water was warm and crystal clear and the fish were astoundingly beautiful. It was the kind of thing that creates a memory that lasts forever.

We had the boat for six hours, so after an hour of snorkeling we decided to dry off on the deck and relax. I put down a towel and laid on my stomach and Henry joined me. We talked, shared salty kisses, and connected in that deep way that only seems to happen on vacation when all of life’s stresses disappear for a little while and you’re free to think about only the most joyous of things.

“Can I give you a massage?” Henry asked after I’d dried off.

“Sure,” I replied. No sane person ever turns down a massage.

He straddled me right there on the deck of the boat and offered a remarkably good massage. I wasn’t exactly stressed out – it was vacation, after all – but there’s nothing like a pair of strong hands moving up and down your back to make a girl feel great.

Henry eventually worked his fingers under my bikini bottoms and pulled them down to rub my ass, which feels a whole lot better than you might think. Figuring he was hoping to fool around a little I moaned, in part because it felt good and in part because I wanted to encourage whatever desire he might be feeling.

Henry leaned down and kissed my lower back. He lips lingered against my skin and it felt surprisingly good. He then moved a little lower and kissed the tops of my ass cheeks. I wondered if he had a destination in mind but I wasn’t quite sure. It seemed entirely possible that he was trying to get me worked up so we could have sex, but Henry rarely initiated in our relationship, mostly because he knew I wasn’t crazy about him trying to take charge.

He then showered my ass with kisses. His lips moved closer to my asshole with each kiss and it became clear that he had a particular destination in mind. I have to admit I found the idea of Henry eating my ass really hot. I’m not always crazy about it – that area isn’t the cleanest part of the body, after all – but we’d just gotten out of the ocean and there’s nothing like an hour long salt bath to clean you up.

I looked back at him and smiled. “Do you want to worship my ass?”

He nodded.

Ever the dominant girlfriend, I reached back, grabbed a handful of his hair, and pulled Henry’s face between my ass cheeks. His tongue went to work immediately and I moaned as I maintained my grip for a few moments longer.

“That’s good, Henry,” I said. “Fuck, that’s so good.”

I released his hair and laid my head on the towel as my boyfriend ate my ass vigorously. It wasn’t one of those moments where I was playing the dominant goddess, but I still felt dominant. He wasn’t eating my ass so he could fuck it. He knew there was no chance of that. He was eating my ass because he wanted to worship me and he probably wanted to worship the slightly naughtier part of me. He was doing it with the energy and desire of a submissive and it thrilled me.

There was something a little bit naughty about it, too. It’s not overwhelming, but it’s just a little bit naughty to know that his tongue was dancing all around my asshole. I bet I could have laid there for another hour and he wouldn’t have stopped, either. I bet he would have worshiped my ass all night long if I wanted him to.

It felt good enough that I wanted to cum, so I said, “Play with my clit.”

Henry’s thumb found its way to my clit and he played with it as instructed. My pleasure deepened and I looked back to see his face buried between my ass cheeks. I’ll tell you, there’s something wonderful about that. Seeing my boyfriend working in service to my pleasure and seeing his face subsumed by my ass was exceptionally arousing.

“You look good like that,” I said. “You look like you belong with your face buried between my ass cheeks. Just like a good submissive.”

Henry groaned and I returned to relaxing on the deck of the boat while he worked to make me cum. I wanted him to really work for it, so I let my mind wander a little.

Eventually he made me climax. It was a damn good orgasm, too. I actually felt my whole body shake for a few moments and I’m pretty sure my toes curled.

“That was lovely,” I said afterwards.

Henry sat up to reveal he had quite the erection in his swimsuit. I’ve always enjoyed a sight like that. To me it’s proof that he’s a genuine submissive. He took great pleasure in eating my ass and making me cum. It got him hard. He wasn’t doing it for an orgasm. It just got him hard to make me feel good.

“Take your swimsuit off,” I said.

Henry stood and stripped and I smiled as his stiff cock popped free.

“Would you like to cum?” I asked.

He nodded and I got up on my knees. There was something about the idea of making him cum on a boat in the middle of the Caribbean that thrilled me, so I took Henry’s cock in my mouth and sucked him off. I gave him an eager, slippery blowjob designed to provide maximum pleasure. I sucked hard and stroked swiftly and soon enough he flooded my mouth.

I took his load and stood up. Henry smiled. He knew what I wanted. I titled my head and our lips met. His mouth opened and so did mine. I fed him his cum. “Swallow,” I said.

Henry swallowed his load like a good submissive should.

“How about we eat that little picnic we brought?” I suggested.

“Sounds good to me,” he answered before grabbing his swimsuit and putting it back on.

Snorkeling, getting my ass worshiped, having a great orgasm, and feeding my boyfriend his cum? That’s a great way to spend a day.

Next time I’ll tell you about how I proposed to Henry.

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MLPESK

hot!