He was my exact type. Long hair, long lean body, a little rough around the edges, and a big cock. He had some tattoos, some First Nation blood that showed in the mocha of his skin so unlike my pale, in the black straight perfection of his hair. He was 6’2, a few inches shorter than me and he loved “older muscular bottom bears”, and he’d been searching for a “daddy to make my boy with my big cock”.
It was seriously fucking flattering. I have a thing for long, lean, hung men. And the long hair: damn. I tried telling him he was too young, that surely he wanted someone closer to his own age, but he was insistent. He wanted me. And I wanted him. But I had a problem: my cock was locked up in a chastity cage, and I was not going to get it out. And this young man needs permission to open my hole.
My status was “Open Relationship”, and that was true. But our bond had become more and more intense, and much to my surprised delight, he had become more and more bdsm and in charge of my sexuality. I literally had nothing to wish for that I didn’t have except that he lived hours away and I only got to be fucked by him every other weekend. I was … mostly content to wait, but even a growingly intense controlling relationship I’d always fantasized about didn’t shave the horny off my up to 14 days of chastity.
I was horny, and this aspiring young man was horny for me and that was flattering. I was normally content to wait, but all the pictures of this raven-haired, beautiful young stud had me worked up. Daily, then hourly, then over and over my normally-content cock was swelling and hurting me as it pressed against the confines of my cock cage. It made me thing of Ginger’s big white cock up inside me, grinding against my prostate, slowly riding me to ecstasy.
But all the chats had me squirming and uncomfortable and aroused like crazy with my cock getting hard again and again and again against the hard metal of my chastity cage. I was horny, and this aspiring young man was horny for me and that was flattering. I was normally content to wait, but all the pictures of this raven-haired, beautiful young stud had me worked up. Daily, then hourly, then over and over my normally-content cock was swelling and hurting me as it pressed against the confines of my cock cage. It made me thing of Ginger’s big white cock up inside me, grinding against my prostate, slowly riding me to ecstasy. But the raven-haired young man was local and wanted to fuck me bad and his cock was thicker and longer than Ginger’s (and I’m not a size queen but something about a heavy, thick cock dangling then swinging, then pointing from a young man’s slender body is hot in a way that bypasses my rationality and makes my prostate pulse with need).
I told the Raven-haired young man that I was locked up and he wouldn’t be able to touch my cock, and that if he wanted to fuck me, he’d have to get Ginger’s permission to open my hole. I thought for sure that would be the end of it, but then the barrage of texts from him really ramped up. It was like he got off thinking about my cock and hole belonging to someone else and him getting to plunder it, seduce it, pleasure me, make me cum from my hole, like it became his obsession even more than it had been.
He took it as a personal challenge to make me ejaculate in the cage (never happened, never gonna happen - you batter my prostate enough, nad my cock shrinks and then I get a little crazy and eventually have a prostate orgasm - shatteringly intense, incredible, but no cum - just the way Ginger liked it!). I was a little stoned and alone on this Friday night, and the raven-haired boy was sending me pictures of his cock and teasing me with the idea of fucking me, and I was getting more and more worked up.
I texted Ginger per our agreement, and he was happy to give the young man permission to open my hole, given certain conditions. I was a little nervous, but I was also very excited. I had been fantasizing about this for a while, and now it was actually happening. The young man was going to fuck me, and if he was as skillful as he was confident, for the first time I was going to ejaculate in the cage. I was going to get pleasure AND release.
Ginger and I had a long chat about the young man, and Ginger assented with humor in his voice, and descriptions of sex that he knew would get me hard and cramped against the cage. I was so grateful for him.
The conditions:
- no unlocking of my cock cage
- he was not to lick of try and fondle my cock
- he was to fuck me hard and fast, and make me cum in the cage
- Ginger got photo proof of the results of sex: both of our cum
- if Raven couldn’t make me ejaculate, he didn’t get to fuck me again
It was a lot of pressure for the young man. It was some pressure for me. Nonetheless, both excited me. Being fucked in the cage, Raven focusing on making me cum as he came. I didn’t know if it was possible, and if it wasn’t I had regrets about not being able to see him again. But if it was possible, I was going to be a very happy boy. I was pent the fuck up here on day 11 since Ginger fucked one of his huge loads into me.
I struggled with feeling “owned” by Ginger, and being “used” by the young man. By which I mean that the traitorous little boy cock held in my cage was aching to be fucked, that it kept swelling hard against its prison over and over as I negotiated with Ginger and planned the visit by Raven.