I was visiting Rob’s new apartment for the first time since he finished the renovations. It was a sprawling three bedroom along Central Park West with an amazing view across Central Park clear across to 5th Avenue. I was never sure how Rob acquired his fortune, but it was fun to experience his world of extreme wealth from time to time.
Outwardly, Rob presented himself to the world as a masculine straight man, though having known him for several years, I knew that he was only interested in men. I also knew that he had a bit of a crush on me, or at least lusted after me. He would often make comments complimenting my body, and one time he even grabbed my ass, though he apologized immediately. What I never told him was that even though I consider myself to be straight, I secretly have always enjoyed the attention, and was even a bit turned on by it.
I kept Rob in mind as I got dressed for the evening. I put on a form fitting polo, jeans which helped to highlight my physique, and my favorite thong underwear underneath. I knew that Rob loved to see men in thongs, and even though we were never physical or romantic, I wanted to feel sexy that evening, and I knew that a thong would do the trick. The truth of the matter was that I wore men’s thong underwear quite often. It felt sexy and I had dated several women who loved seeing me in a thong, so I continued wearing them even though I was single at the moment. I worked out regularly and watched my nutrition, so I had a muscular body which was well suited for a thong, so I decided to enjoy it.
When I arrived at Rob’s place, I was absolutely amazed. The apartment was meticulously renovated and incredibly spacious, and not just by New York City standards. As he gave me the grand tour, I could sense him walking behind me, and I even caught a glimpse of him checking out my ass. He smiled and winked when he saw that I noticed, and I smiled back. We both enjoyed the flirtatious overtones of our relationship even though we had no expectations of ever hooking up.
Once the tour was finished, I asked Rob about one final room which he had yet to show me. He looked a bit embarrassed before he told me he was afraid that showing me the room might make me a bit uncomfortable. I couldn’t imagine what he meant, so I pushed to see the room. Eventually he gave in and led me to a small sound-proofed room adjacent to his kitchen. It seemed to have once been designed as a room for staff to occupy, but in the 21st century it served whichever purpose the owner needed. In Rob’s case, that purpose seemed to be an S&M dungeon or sex room.
He examined my face as he led me into the room. I’ve always had a kinky side to me, so I enjoyed taking it all in. There was a metal cage, a rack, ropes, dildos of various sizes, and numerous other toys. However, my eyes were drawn to a shelf of metal chastity cages. I walked over and began examining them one by one. Rob walked closer to me with a huge smile on his face.
“Do you know what those are?” he asked. I nodded yes.
“Do you have many guests who wear these?” I asked.
“No, and actually, you’re my first guest. These are all brand new. I’ve always wanted to be someone’s keyholder, but never found anyone interested in wearing a chastity cage for me” he lamented.
I had always fantasized about wearing a chastity cage, but in my mind, it was always with a woman holding the key. That said, why should this be any different? Perhaps it would be fun to try wearing a cage. And if the key would be held by a man, why not have that man be Rob? I decided to proposition him.
“Do you think I could try on one of these cages? I’ve always been curious about male chastity” I asked.
He gave a huge smile and invited me to pick one out. We agreed that he would leave me alone in the room while I found the right cage with the right fit. Once he left, I began to try them on one by one. After trying on three of four, I found one which fit perfectly. I then helped myself to some of the Auquaphor skin ointment that was sitting on a nearby shelf. I had read that when wearing a male chastity cage, it was necessary to use some lube, and I suspected that the Aquaphor would do the trick. I then washed the Auquaphor off my hands in the adjacent bathroom, put my thong back on over my new stainless steel chastity cage, and neatly folded my clothes and left them on a chair as I walked out to hand Rob the key to the chastity cage.
I walked through the apartment in my thong looking for him until I found him relaxing on the plush sofa in the massive living room. As I handed him the key, he smiled and motioned for me to turn around. As I turned around to let him see my body, I could see that he was visibly excited. He was practically on the edge of his seat checking me out. I was self conscious, but quite aroused also. I was always a bit of an exhibitionist, and I truly loved being on display for him. It didn’t matter that he was a guy, and in fact, that made it even more exciting as it felt slightly taboo. I leaned into the experience and found myself loving every second.
“I’ll be holding onto this, and possibly for quite some time” Rob said as he placed the key to my chastity cage into his pocket. I could feel my cock struggling to grow erect inside of my chastity cage.
“Let me see the cage” he said.
I pulled my thong down to reveal the cage locked around my cock. Rob’s smile grew.
“Tell me how it feels to be locked in chastity. I want to hear every detail” he ordered.
“Honestly, it’s kind of a huge turn on” I said. I continued, “ I love feeling my cock struggling inside of the cage, especially knowing that you’re holding the key. Part of me feels like I’d do anything for you to unlock it, but the other part of me wishes that you’d leave me locked in this chastity cage forever. I’m rather surprised by how much it turns me on.”
He smiled and responded “Good. Perhaps I will leave you locked in chastity forever. We’ll have to see. But first I have to go lock this key in my safe.”
He then got up and left the room, only to return a few minutes later wearing only his underwear and with no key in sight. I had no idea where the key was, nor did I care. I was slightly anxious about not knowing where it was, but those thoughts were overshadowed by how aroused I was feeling the chastity cage locked around my cock.
As Rob lay sprawled out on the sofa, I suddenly couldn’t help myself and walked over to join him. When I sat next to him, his hand began to caress my chest and I found myself growing even more aroused. I positioned myself so that he could see and access my ass, and he immediately took the bait. It felt nice to feel his hands on my butt cheeks, and then tracing the outline of my thong between my cheeks. I was moaning by now, and growing incredibly turned on. I was wondering what it would feel like to feel his cock in my mouth, and perhaps even in my ass.
I turned around and faced him, not touching his chest with my hands. As he leaned back and closed his eyes, I moved my hands lower and lower, eventually running them over the outline of his hard cock under his underwear. Before I could go further, he slid his underwear off, revealing his hard cock. I leaned down and took it in my mouth. I slid as much of it into my mouth as I could, caressing it with my tongue and stroking the remaining part of it with my hand. He was clearly enjoying it, and I hoped I was giving him what he wanted.
I continued blowing him for a while until he began moaning with such intensity that it seemed like he was approaching orgasm. By now, I was fully into the moment and truly wanted to feel his cock inside of my ass. I couldn’t even wait to remove my thong. I simply straddled him and pulled my thong to one side once I covered his cock with enough of my saliva to lubricate it sufficiently.
I was so aroused that his cock slid into my asshole quite easily and he moaned as it did so. I sat on top of him and pushed down with my ass to bring him as deep inside of me as possible. He exhaled deeply as I did so, and I began to grind on him. As I fucked him, he resumed his moaning, and was clearly loving being inside of me. I began to grind deeper, harder, and faster. I felt almost as though I might cum if it weren’t for the chastity cage locked around my cock. By now, he was approaching orgasm and I desperately wanted to make him cum, so I listened to his body and fucked his cock with my asshole as passionately as I could.
I could see Rob leaning back with his eyes closed, breathing heavily. I watched his face as I drove his cock deeper and deeper inside of me. I was now grinding on him quickly and deeply enough that I was nearly out of breath, but couldn’t resist continuing. I desperately wanted to feel him cum inside of me, and I wanted very much to please him. His moaning grew louder and more intense, and I could tell he was about to cum. I squeezed my butt cheeks together as I rode his cock in anticipation of his orgasm.
In less than a minute later, he suddenly drove his hips toward me and his cock deeper inside of me as I felt his load ejaculate inside of me. It came in several waves and I was so excited that it was nearly enough to make me cum myself. I was glad to be locked in the chastity cage as it made it more difficult for me to cum, and I was grateful to be denied my own orgasm. I just wanted to please Rob.
Once he was finished shooting his load inside of me, he pulled out and relaxed on the sofa. I found myself loving the feeling of having his load inside of me, slowly dripping out. I pulled my thong back on so his cum would drip onto it and not onto his sofa. I leaned over and took his cock into my mouth again to lick up the mess. Once I cleaned up his cum from his cock, and lay beside him and rested my head on his chest. The look on his face appeared completely satisfied, and I was thrilled to have been able to help facilitate that. I was more aroused than I could ever remember having been, and I was glad to be locked in chastity so that I could have the opportunity to satisfy him again once he grew hard again.