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, we’d gotten more intense and in small and then large ways he had really come to be in charge of my sexuality. I 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.
All our chats had me squirming and uncomfortable and aroused like crazy with my cock getting mostly 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 aching as it pressed against the confines of my cock cage. It made me thing of Ginger’s big white uncut 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).
Maybe it was a little shame I had about my cock not being free, about really committing to Ginger as my dom and me dropping in as his sub bottom. We hadn’t negotiated permission the two of us, but I knew it was what Ginger wanted. I decided to step into the edge of shame I was feeling about my cock all little and locked up. I texted Raven, came clean - my cock is in a chastity cage I can’t remove, and while I can get chubbed hard, I can’t come - and not only that, but to build intensity between us, my Ginger wants to approve boys who fuck me.
I bit my lip and stared at the send button. Horniness and shame built on each other inside me. My balls stirred in their sack. My dick chubbed to max in the cage. My ass got hungry (can your prostate swell?), there was a hot need in the bottom of my belly. I wanted to jerk off and found myself experienced that inability as pleasure, as a hot freedom, as armor, as a kind of horny safety I always wanted.
I told the suitor 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. The ”…” on texts from Raven went on for a long time - someone struggling with what to communicate.
Finally, the message was short. It was going to be some kind of fuck off. I sighed and pulled it up. “How do I request sir’s permission to really please that hot furry muscle hole of yours and force you to cum!? I need to corrupt you ASAP - so 4rny here!”
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 pulled him in in a way he hadn’t been before. I was surprised. Something turned in me. Some little hot shame came alive and my big balls were moving in their sack.
The messages came hot and furious. He was really excited now and getting creative. He decided on a goal to work up to - with a lot of practice - to make me ejaculate in the cage (never happened…you batter my prostate enough, nad my cock shrinks and then I get overwhelmed in the best way 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 eating me out til I begged for his cock. I guess I was the one getting worked up.
I texted Ginger, and told him Raven had asked for his digits so that he could seduce me and try and make me cum in my cage. Ginger sent me his wicked copper-bearded smile. I’d been fantasizing bout this for a while since Ginger finally agreed to lock up my cock. I was nervous and excited what was coming next. I was fantasizing about him actually making me cum in the cage just from arousing my ass, my nips, my balls, my body.
The phone rang and it was Ginger. I was surprised, picked up on the half-ring. “Well, good bear, you all excited to have this boy make your ass happy for me?” I melted talking to him. I wondered why I wanted Raven at all. He asked me questions, humor in his voice, desire, no jealousy. He talked flirtatiously - in ways he knew would get me chubbed in my cage. He grinned when he saw me adjust myself. Finally he said, “Of course, bear, but this boy needs to respect you. So here’s how we are gonna make sure of that…”
I felt him like a jacket on a cool night, like a tight workout shirt on chest day, like a blanket under the stars on a warm night. And he wanted me to want this boy, to open to this boy, to give myself to this boy, as long as Raven deserved me. I was so hard in my cage it was insane. I couldn’t believe I felt like this, could feel like this.
Ginger’s conditions:
- no unlocking the cock cage
- Raven can work my big balls that love attention, but has to avoid my cock
- Raven was to fuck me to at least give me a prostate orgasm before he came in me
- Ginger got photo proof of the results of sex: any cum that was spilled (Ginger liked me to hold his seed, but not other men’s)
- if Raven couldn’t make me have a prostate orgasm, he didn’t get to fuck me again
- if he made me ejaculate, he had to commit to fucking me again
It was a lot of pressure for the young man. It was pressure for me. Both excited me. Being fucked in the cage, Raven focusing on making me cum. not his own pleasure… 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 sat in my comfortable chair after the conversation with Ginger. I felt owned by him. Some part of me got a fattie against my cage every time I considered what was happening. A deep part of me wanted to feel like I belonged… to a man. To hot, hot, beautiful-dicked Ginger.
I felt the rush of being desired by this younger man, Raven, with a big club cock, long hair, mischievous smile, and a desire for me I couldn’t imagine deserving. He wanted to do everything. He wanted to work me, impress me - me, who didn’t feel that sexy. Dayum! I was the luckiest man…
“You free in an hour?” Raven asked me, knowing, I think, how horny I was now. I could practically feel how horny he was. “Can I come over? We don’t have to do anything, I just want to kiss you.” The little liar.
“Sounds great,” I followed with my address. I needed to get ready.
He was on me before I backed through the front door to let him in. He was 8 inches shorter than me, so he reached up with one hand, grabbing the back of my neck, pulling me down as he leaned in and forward, going up on his toes to meet out mouths. Full, sensual kisses with thick lips, soft at first but with rising intensity. He fished my tongue out of my mouth, writhing them together, pulled it into his and started sucking on it with moderate intensity. It was intensely erotic and the hot tightness in my cage made me moan like a whore. It egged him on, kissing, and pawing at my big pecs, my round belly, my ass. Then his hands found my big balls pulled tight under the hard surface of my cage. His fingers gripped my whole package, long cool digits stroking and caressing and squeezing at the outlines - the ring behind my balls, the cage hooded over the small size of my quiescent cock now straining to contain my grower.
He pulled back and looked up at me in the eyes as he brought a second hand down to cup the cage and thump at my balls, “Oh, my god,” he said with the happiest brightness in his eyes. I needed the fucking cage off and to have those long slender fingers on my junk. But that wasn’t going to happen. My blue eyes and his witch hazel met in the knowing that there was no letting out this cock, no easy getting me off. He pressed against me and I felt the long throb of his member against my thigh. Jesus, he was up for the challenge.
He felt me relax and sign when his cock pressed its length against me. He reached for the waistband of my shorts, “May I?” I just nodded and he pushed the cargo shorts down over the big round swell of my muscular ass cheeks.
I was wearing a white jockstrap, just the way he liked. The ring and the cage propped up my already-big balls and pushed them forward, making the bulge much larger.