I'd been seeing Perry for a few months, or at least we'd been hanging out and fucking a lot. He expanded my world in a multitude of ways. He introduced me to CBT, which I've now grown rather fond of and have been looking for new players. He let me play with his ass and explore in ways that no one had ever allowed me to. We'd had threesomes, both of a MFF and MMF variety, which I'd enjoyed every minute of. We had embarked on a wonderfully exciting sexual voyage.
The culmination of this was when we decided to try male chastity. His limp, little cock would be locked away until I decided otherwise. So he came over for me to ceremoniously lock his favorite parts away. Being the kind, caring, partner that I am, I decided that he should get to cum one last time.
But this should be no run of the mill orgasm, I wanted this to be spectacular. Now, Perry is, if nothing else, a total pain slut. I've done things to his testicles that I was sure would cause permanent damage. Perhaps there's a reason he's childless. So I put him on hands and knees on my bed. I grabbed my favorite riding crop, which was his, but which I have since commandeered, and started working him. I'd used one of my hair ties to bind his balls and they were presented to me so beautifully. A nice soft, round target for the harsh sting of the crop.
The benefit of a bigger man, or woman, is more surface area. There are more places to hit, to tease, to torment, to inflame. I worked all over his ass, legs, cock and balls. The snap of that crop striking flesh is sublime and very arousing. My pussy was wet and achy five minutes into the night, and the pretty little pink marks I was leaving all over only added to my arousal.
Quite some time later, when I'd concluded that he'd had enough, and didn't want the neighbors think I was torturing anyone, I decided to give his ass the attention that I knew it wanted. I kissed his sore spots and then focused my tongue on his tight asshole. The soft moans that I was rewarded with urged me on. I licked and sucked, pushing my tongue in just slightly, feeling him open up to me. I quickly realized that my tongue wasn't going to be enough so I grabbed the lube.
Now when I say Perry is tight, I mean tight. This is a man who's had at least as much anal penetration in his life time as I have, and yet, even the insertion of one finger feel like its in a vise. I started working my one finger in and out, loosing and stretching for the bigger things to come. Then I pushed in a second. I found his prostate and began stroking it. The sounds he made were almost ethereal, they were just so beautiful. It was the sound of complete satisfaction and submission and I loved it. I ordered him to stroke his cock while I delightfully played inside of him. I think that may be why I enjoy stimulating a man anally so much. It allows for a type of control and possession that simply isn't achieved otherwise.
He continued stroking while I pulled my fingers out and wriggled into my strap-on. Just the act of sliding it on and tightening the straps, pulling it near my yearing cunt almost sent me over the edge. I was about to penetrate someone in a way I'd never done before, and though I couldn't actually feel it, my mind filled in the blanks for me pretty well.
I walked up behind him and pressed the head of my good sized black toy against his hole and I asked him what he wanted. The words "I want you to fuck me," we're the sweetest and most erotic I'd ever heard. I obliged, pushing the head inside slowly. I've taken anal enough to know to be slow and gentle. Inch by inch I slid in, my lube covered cock penetrating his tight orifice. Once I was all the way in, I held it for a while to let him acclimate to having his ass filled. Then gradually, I started pumping back and forth, in and out. Meeting no resistance, I began increasing my speed and intensity. Before long, I was slamming all the way in to him. I would pull out to admire the gaping asshole begging to be filled again. One of the things I love about Perry is how vocal he is, and he is a screamer. He's reached pitches and volumes that most women would be envious of.
I had my hands firmly planted on his ass, spreading his cheeks so I could see that fake cock slid in and out. All the urge and desire I'd ever had to use a man as so many had used me was manifested in this moment. I knew be was close to cumming when the screams became louder and closer together. I was relentless, everything else in the world had dropped off and we were in a sphere of pure pleasure. He hit a high soprano note, and then collapsed on the bed. I pulled out gently and laid down next to him.
The rest of the night is a little fuzzy. I think I may have had him help me pleasure myself and then I put his cage on. That experience didn't turn out so well and we've since transitioned into a more intimate, less sexual relationship. But that night will be one of my fondest memories of him and will provide masturbatory material for years.
The culmination of this was when we decided to try male chastity. His limp, little cock would be locked away until I decided otherwise. So he came over for me to ceremoniously lock his favorite parts away. Being the kind, caring, partner that I am, I decided that he should get to cum one last time.
But this should be no run of the mill orgasm, I wanted this to be spectacular. Now, Perry is, if nothing else, a total pain slut. I've done things to his testicles that I was sure would cause permanent damage. Perhaps there's a reason he's childless. So I put him on hands and knees on my bed. I grabbed my favorite riding crop, which was his, but which I have since commandeered, and started working him. I'd used one of my hair ties to bind his balls and they were presented to me so beautifully. A nice soft, round target for the harsh sting of the crop.
The benefit of a bigger man, or woman, is more surface area. There are more places to hit, to tease, to torment, to inflame. I worked all over his ass, legs, cock and balls. The snap of that crop striking flesh is sublime and very arousing. My pussy was wet and achy five minutes into the night, and the pretty little pink marks I was leaving all over only added to my arousal.
Quite some time later, when I'd concluded that he'd had enough, and didn't want the neighbors think I was torturing anyone, I decided to give his ass the attention that I knew it wanted. I kissed his sore spots and then focused my tongue on his tight asshole. The soft moans that I was rewarded with urged me on. I licked and sucked, pushing my tongue in just slightly, feeling him open up to me. I quickly realized that my tongue wasn't going to be enough so I grabbed the lube.
Now when I say Perry is tight, I mean tight. This is a man who's had at least as much anal penetration in his life time as I have, and yet, even the insertion of one finger feel like its in a vise. I started working my one finger in and out, loosing and stretching for the bigger things to come. Then I pushed in a second. I found his prostate and began stroking it. The sounds he made were almost ethereal, they were just so beautiful. It was the sound of complete satisfaction and submission and I loved it. I ordered him to stroke his cock while I delightfully played inside of him. I think that may be why I enjoy stimulating a man anally so much. It allows for a type of control and possession that simply isn't achieved otherwise.
He continued stroking while I pulled my fingers out and wriggled into my strap-on. Just the act of sliding it on and tightening the straps, pulling it near my yearing cunt almost sent me over the edge. I was about to penetrate someone in a way I'd never done before, and though I couldn't actually feel it, my mind filled in the blanks for me pretty well.
I walked up behind him and pressed the head of my good sized black toy against his hole and I asked him what he wanted. The words "I want you to fuck me," we're the sweetest and most erotic I'd ever heard. I obliged, pushing the head inside slowly. I've taken anal enough to know to be slow and gentle. Inch by inch I slid in, my lube covered cock penetrating his tight orifice. Once I was all the way in, I held it for a while to let him acclimate to having his ass filled. Then gradually, I started pumping back and forth, in and out. Meeting no resistance, I began increasing my speed and intensity. Before long, I was slamming all the way in to him. I would pull out to admire the gaping asshole begging to be filled again. One of the things I love about Perry is how vocal he is, and he is a screamer. He's reached pitches and volumes that most women would be envious of.
I had my hands firmly planted on his ass, spreading his cheeks so I could see that fake cock slid in and out. All the urge and desire I'd ever had to use a man as so many had used me was manifested in this moment. I knew be was close to cumming when the screams became louder and closer together. I was relentless, everything else in the world had dropped off and we were in a sphere of pure pleasure. He hit a high soprano note, and then collapsed on the bed. I pulled out gently and laid down next to him.
The rest of the night is a little fuzzy. I think I may have had him help me pleasure myself and then I put his cage on. That experience didn't turn out so well and we've since transitioned into a more intimate, less sexual relationship. But that night will be one of my fondest memories of him and will provide masturbatory material for years.