Chastity with Ex as Keyholder Ch. 07


The only light came from the crack at the bottom of the floor. I tested my handcuffs as quietly as possible, verifying there was no way to squeeze my wrists out of their cold, metal clutches. I was completely stuck.

I could hear my Ex on the other side of the door. She was panting heavily. I could only imagine her Boyfriend’s cock ramming her inside and out, over and over again.

I guess I should back up just a little bit, although there is still more to tell about other happenings, but this is the part most readily on my mind. After my Ex’s Boyfriend came home, my Ex summoned me to their bedroom. She pushed me into their walk-in closet and forced me to the floor, where she stood over me in her awesomely hot high school cheerleading uniform, complete with pantyhose and the shiny bodysuit. Her pantyhose covered knees were inches in front of me face as she told me what was about to happen.

“Glad you were enjoying yourself out there, worshipping princess Kara’s shoes and all. Don’t mind the fact you didn’t ask permission. I suppose the humiliation of doing it in front of the whole party is enough, but I think you should still be punished. You see, my Boyfriend was the quarterback in high school and he always had a thing for the cheerleaders. I’ve never worn this outfit for him before, so as soon as he came home he told me he had to fuck me.

“So, I figured you would just love to listen to what a real man sounds like when he’s fucking me, especially since that tiny metal cage is keeping you from having any pleasure or erections at all. But, just to be on the safe side,” she had said, pulling out a pair of police grade handcuffs.

“Now, kiss my shoes before we start this thing,” she said, putting her hands on her hips.

If my cock hadn’t been completely helpless in chastity, I know I would have cum at this exact moment. Here was my hot, beautiful Ex, dressed up as a high school cheerleader with her hands on her hips holding metal handcuffs, ordering me to kiss her shoes. If not for the chastity cage, I would have been cumming all over the place.

They smelled like plastic and pantyhose, but I kissed her shoes regardless. If the girls in high school had known what it would have taken for me to be their little bitch, I’m sure I would have had a much more interesting experience.

As it was, I worshipped every inch of my Ex’s shoe, making it as shiny and new as possible. She seemed to appreciate it as she admired how awesome her bright white shoes were looking.

“Gee, I should just have you come by more often and do this with all my shoes,” she joked. “But this isn’t about you, is it?” she said raising her leg, pushing my chest against the floor.

“You didn’t ask permission to worship Kara’s feet, so now what can I do? The original punishment I had in mind for tonight seems tame in light of this indiscretion of yours,” she said, her pantyhose just inches from my mouth. My cock was desperately struggling to find its way to erection, but the metal cage was more than it could handle.

“Regardless,” my Ex said, pushing me down with her legs, “Enjoy the next half hour.”

With that, the door was closed and I could hear her boyfriend enter the room, obviously a little tipsy. He absolutely loved her uniform and the pantyhose. In fact, for a brief moment, I thought I could maybe even relate to this guy on some sort of kinky level until I heard him rip off the pantyhose and start drilling my Ex like there was no tomorrow.

Meanwhile, my little cock ached inside of its cage. She had called me and allowed me to listen to her getting fucked by her boyfriend multiple times, but being there made it a little different. Being just a few feet away in the closet, hearing every little sound, moan, and groan of pleasure made the experience all the more humiliating.

Dressed up like a sissy maid, handcuffed, and having been denied orgasm for what felt like forever at this point, with my angry little dick ferociously pressing against the limits of the cock cage, the image of my Ex in her hot little cheerleader outfit and pantyhose—it was almost more than I could handle. The only bit of relief was from the tiny dribbles of precum that oozed out of the tip of my cock. My panties were nice and wet at this point, just like a real pussy. And for some reason, even this thought made me aroused!

Without realizing it, I was moving my hips and grinding my cage against my frilly, satin panties. Reaching around as best I could with my handcuffed hands, I desperately tried to stroke my imprisoned little cock. The metal cage was mostly solid, but it did have some limited access to my tortured, constantly aroused little penis.

I didn’t even want to think about what my Ex would say if she knew what I was trying to do. Yes, my Ex…suddenly, I realized it had gotten quiet on the other side of the door. And then I realized I had no idea where their sex had left off. Did he cum? Did she? Why was it so quiet and I could barely make out their whispers.

“So Nevşehir Escort you remember what we talked about?” I could hear my Ex say.

“Of course, how could I forget,” the Boyfriend said with much less care of being quiet. “Mhmm, I love it when you stroke my cock like that.”


“Well, what if we moved things up a bit?” she said, her voice slightly more seductive.

“I suppose. Is everything ready?”

My Ex giggled and whispered something so quietly I couldn’t even make it out. But I could definitely pick out the footsteps. The footsteps were coming towards the closet. I had nowhere to hide, so I simply knelt there like a chaste little sissy boy.

The door opened. Standing in front of me was my half clothed Ex in what remained of her cheerleader uniform. Next to her was the Boyfriend, half dressed in a jersey and a very, very large cock pointed directly at me.

“He looks very surprised,” the Boyfriend said. “Stand up and come out here,” he commanded. His voice was deep and almost soothing.

Feeling very self-conscious, I did as he said. My hands, cuffed behind my back, made it somewhat difficult to stand up, but I made it out to the middle of the room.

“God, you almost pass for a girl,” he said, his hands groping my thighs.

What the hell was happening? And why was I liking it and getting more aroused? I didn’t normally get off thinking about guys, but I guess I had never been locked up in chastity, dressed up, and then fondled by what girls would call a very hot guy– whatever, putting sexuality aside, he was a hot guy. His abs were ripped, his arms looked like they were molded from a P-90X commercial, and he had these weird eyes that were kind of authentic.

I tensed as his hands felt up my legs, all the way to my cock cage. He cupped it in his hands, his breath on the back of my neck.

“All locked up like a good sissy bitch,” He said, tapping the cage every few seconds.

I couldn’t help myself from moaning. It did feel good.

My Ex was lying on the bed at this point, rubbing her exposed clit, biting her lip.

“This is so hot,” she said, watching her Boyfriend grope me through my maid uniform. “If you want any hope at being out of chastity, then you have to do exactly what we say,” she said.

“I…I don’t understand,” I said as the Boyfriend gently pushed on my shoulders until I was on my knees, his cock inches from my face.

“You don’t have to understand,” my Ex said. “Just do what you want to do. Just do what is natural to you.”

Before I knew what I was doing, the Boyfriend’s cock was in my mouth. I had no idea what I was doing, but I couldn’t help myself. I had never thought of myself as bi or gay, but being dressed up like this, being denied orgasm this long, and having a giant cock in front of me, it did feel natural to go after it.

To my own astonishment, the Boyfriend didn’t hit me or knock me down. He groaned in satisfaction.

“Oh yeah, I love newbie blowjobs,” he said. “You look so much like a girl, how’s it feel to suck a real cock?”

I couldn’t respond since my mouth was, in fact, full of his cock. I morbidly didn’t want to do a bad job, either. It tasted salty, and slightly like my Ex since he had been fucking her before violating my mouth.

It was hard and soft at the same time, but mostly hard. Only in my deepest, darkest fantasies had I ever dreamt of experiencing something like this. My Ex, still partially dressed in her cheerleader uniform rubbing her clit while I, the locked up chastity sissy, sucked her Boyfriends giant cock.

“That’s the closest you’ll to get to cum in a long while,” my Ex giggled, breathing harder and harder while the Boyfriend began grinding his hips, pushing his giant cock further down my throat. Meanwhile, my own cock strained in futility against the metal confines of its cage. At least with the plastic cage I had some hope it might break or split or fail, but this metal cage was completely solid. It would take a hacksaw to get this thing off, and the odds of doing that without hurting myself weren’t very good. At least, not good enough for me to have tried.

Plus, then there was all the blackmail my Ex had against me. Speaking of which…


Pulling my mouth away, I blinked, looking over at my Ex who had grabbed a quick picture of me sucking cock.

“Don’t worry, it’s just his face,” my Ex said to her lover.

“I trust you,” he said, slapping me somewhat forcefully. “You don’t stop sucking cock until told so, got it, sissy?”

Why was my cock responding to this? This was wrong, way wrong. I liked girls. I liked having sex with girls, not sucking my Ex’s Boyfriend’s cock. Yet, for some reason, being in this particular situation, I couldn’t help myself. I was literally the sissy, chastity maid I had always fantasized about, but the reality of it hit me like a ton of bricks.

He would cum. I would not. End of story.

And as instructed, I began sucking Nevşehir Escort Bayan and fucking his huge cock with my virgin mouth. My lip and neck muscles began to ache, but I didn’t want to stop again in fear of what they might do.

“Oh yes, make him cum in your mouth,” my Ex moaned from the bed, rubbing her clit faster and faster.

“How’s it feel being such a little chastity slut that the closest you get to orgasm is sucking the cock of your Ex’s Boyfriend?” he said, mocking me as I went down on him.

I couldn’t believe what I was doing, or to the more scary fact that I actually enjoyed it in some horribly kinky way.

Argh, why was his voice so smooth? It was like silk on my soul. I couldn’t deny it, yet at the same time it went against everything I knew. I kept licking his salty, giant cock, reveling in his pleasure vicariously since my own cock was denied any sort of pleasure.

“You were so worried about me finding out,” he said, groaning. “But I bet you never thought I’d be into this, did you?”

Meanwhile my Ex must have reached orgasm on the bed watching this entire scene fold out because she began to squeak and jerk as she touched herself.

I, of course, remained constantly aroused, teased, and frustrated.

“You see, I don’t think in terms of gender. I think in terms of power. Right now, I have the ultimate power over you, sissy slave. I have the power of your cock and whether you ever get to have an orgasm again, and when that orgasm will be and under what conditions.”

Having my Ex as the keyholder was bad, but this was even worse. My Ex’s Boyfriend also holding the key to my cock? I had never felt so humiliated in my life.

“Do you like the taste of cock, chastity sissy?” he asked calmly.

As meekly as possible, I responded, “Yes.”

And I truly did, I had just never known it, and I would never have known it unless someone shoved their cock in my mouth like this. I had always felt that my dressing up had been missing something. I loved the feeling of tights, pantyhose, petticoats, dresses, and everything like that. But once dressed up, it had felt like a piece was missing. Teasing myself and looking at pictures of cute girls in pantyhose helped, but now I knew it wasn’t the answer.

“A little different than the strap-on, is it?” my Ex said from the bed, still slowly rubbing her clit and keeping herself at climax. “I always had a feeling you’d like the real thing, just needed the proper motivation.”

And so here I was. I was completely shaved, dressed up like a little French Maid with full make-up, wig, and heels. Apparently I made a hot maid since several of the guys at the party hit on me before realizing I was a guy. Anyway, my Ex was half naked on the bed, masturbating, while her Boyfriend stood over me with his cock in my mouth. Oh yeah, and my cock was locked up in chastity, and no one had said anything about letting me out.

“I want to see you cum in his mouth,” my Ex said from the bed. She looked so hot in her cheerleader top and ripped pantyhose, but giving orders like that multiplied how horny she could make me.

“I bet you love the taste of cum, especially since you can’t make your own now,” the Boyfriend said. “Think you can make me cum?”

I submissively nodded my head yes, still unable to even talk about what was happening.

“Are you sure? I think you might need some additional motivation,” he said looking over at my Ex, nodding his head.

I didn’t know what they were up to, but I was curious at this point. What else could possibly happen that would shock me at this point?

I continued to suck and lick the Boyfriend’s monster cock. His cock was not average. I had considered myself average, and he was easily twice my size…unless I wasn’t as average as I had thought!

I found myself getting off on the way he moaned and shifted his weight as I concentrated on the tip, which is what I had always liked. Circling his head with my tongue while I stroked the base of his cock with my hands seemed to hit the spot for him.

“This little bitch learns fast,” he said to his Ex. I heard her rummaging in the closet, but concentrated on the cock in front of me.

“Is he doing good?” she said.

“Hell yes, I might even cum before you get out here.”

I continued to focus on his head, teasing it slightly and going more slowly. Maybe if I did a good enough job, they would let me out of chastity and this whole ordeal would end.

Then I wondered if I wanted it to end. If I was given the orgasm, what would happen? In my brief period of non-horniness, would I grab my crap and demand a ride home? Usually after I had an orgasm, the play time was over and I didn’t want to be dressed up anymore. Well, it wouldn’t be my decision either way. Judging by the amount of money my Ex had sunk into the chastity device I was currently wearing, she and her Boyfriend would be expecting some decent mileage out of it.

“Ready!” my Ex said, Escort Nevşehir emerging from the closet.

She had found her strap-on dildo! I thought she had gotten rid of it when I broke up with her.

“Of course I kept it,” she said, noticing my surprise. “I fucked it almost every night after we broke up. But now, it’s going to be fucking you.”

“You’ll need to move to the bed now,” the Boyfriend said, gently standing me up by the shoulders. “God, you make such a hot little sissy.”

My cheeks burned red with a mixture of pride and embarrassment. No man had ever openly admitted any sort of attraction to me, but it felt…great, especially since it was because of how well I came off as a girl.

“I could almost take you out in public,” he said, walking over to the other side of the bed while my Ex situated herself behind me.

The Boyfriend stood in front of me, his cock large and aroused. Precum slowly drizzled out the tip, and I found myself grabbing it suddenly so I could catch it. Salty and warm on my tongue, I couldn’t help myself.

“Oh my, you were so right about him,” the Boyfriend said.

“I know,” my Ex said spritely as she slowly pushed her now lubed up strap-on into my ass.

I moaned loudly as she entered me, inch by inch. I hadn’t had anything in my ass for a while, so it was a little uncomfortable at first.

“Now, you get to fuck my strap-on while sucking cock,” she said as she began to move her hips back and forth.

Suddenly, I felt ooze dribbling out of my own cock.

“This is the closest you’ll get to cum,” my Ex said. “My strap-on pushing on your prostate will cause you to jizz, but it won’t be the same as a real orgasm. It’ll be slow, and it’ll be torture, but it’ll empty your balls and keep you locked up for us.”

I attacked the Boyfriend’s cock as my Ex spoke to me. She hadn’t been this dominant when we were together, but now she had her Boyfriend to dominate her. And I loved it.

It was almost more than I could bear. My Ex was drilling me from behind while I sucked on her Boyfriend’s cock, with a locked up cock and dressed as a sissy little Maid. I could never have imagined a situation like this. I figured her Boyfriend was some stereotypical Alpha male type who would have beaten the living shit out of me had he known what me and my Ex were up to.

It was the exact opposite.

“I’m almost there,” he said as I continued to work on his cock.

Meanwhile, my Ex continued to pound me in the ass, causing ever increasing dribbles of cum to ooze out of my cock. She was right. It was almost like cumming in slow motion. Every few moments, I could feel the cum slowly exit my cock, but it wasn’t satisfying by any means. In fact, it made me even more horny, which must have been the torture part she talked about.

“Yes, yes,” he said, grinding his hips.

And then it happened like an explosion. Suddenly, hot cum shot into my mouth, coating the back of my throat. I kept on stroking and sucking until he stepped away, motioning me to stop.

It tasted weird, and the consistency was unlike anything I had ever had in my mouth. I wanted to gag at first, but forced myself to take it.

“What a good little sissy,” the Boyfriend said.

“I think he’s been properly milked by my ass ramming,” my Ex stated, pulling out of my ass.

I allowed myself a momentary respite on the bed, laying down after it was all over.

The Boyfriend had orgasmed, my Ex had orgasmed several times, and I supposed I technically orgasmed, although it didn’t feel that way. There was a large pool of cum in my panties, but I was just more horny than ever.

The Boyfriend and my Ex got dressed in what I assumed were their PJ’s. The Boyfriend sported some tight boxers and a shirt while my Ex simply threw a tank top on with her panties.

“You want a drink?” he asked.

I nodded.

The party had ended long ago and the rest of the apartment was empty.

The Boyfriend poured me a stiff shot of whiskey.

“You did pretty good in there,” he said, almost like we were talking about a football game. “I’m more than impressed. She said you’d be a good candidate, but I had no idea.”

Candidate? Candidate for what?

“I bet you’re thinking to yourself of where do we go from here? I know you love worshiping my girlfriend’s feet, which is what got this whole thing started. You didn’t think it was by some accident that she showed up at your place, did you?”

I took a long sip of that drink.

“I don’t know what to think,” I said.

“Of course not. We’ve been looking for a sissy, if that helps make this whole thing any sense. We met a couple folks online, but they weren’t right. And then, you were mentioned. The idea seemed perfect. My girlfriend’s ex boyfriend as the sissy! But when she came to see you that day, everything changed. You had decided to explore chastity.”

By this point, my Ex had sat down at the table with her own drink.

“You really did this to yourself,” she said, smirking.

“She needed to act fast and took your keys. We set up the scenario for her come over after work and dominate you, something which we’ll continue to do since she enjoys it so much. But the question is does she need to come over?”

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