Do You Remember Your First Time In Chastity?

I remember when it all started.  People always say that big days mean something and you remember them vividly but that doesn't always happen.  You may think you remember them but there are always details that fade in and out each time you tell the story.  There are aspects of it you gloss over because they've become smudged along the edges of the picture in your mind.  You remember them vividly the way you can sing old songs off the radio; the chorus is bang on but the rest of the beats are slightly off.

This wasn't one of those times though.  It was something that was almost telegraphed and laid out perfectly as it was getting closer.  The funny thing is there was no guarantee that it was ever going to happen.  It just did one day and everything else changed after that.

We were laying there, my wife and I, and she was running her fingers over my cock.  It was a teasing thing that I liked her to do before I jerked off.  I hadn't been able to make her cum in quite some time and she preferred her toys as they always did the job perfectly.  We discussed it and I didn't want her to be frustrated anymore.  So she would tease my cock until it got hard and then I would finish off by jerking until I had an orgasm.

She was whispering in my ear.  Teasing me and telling me that she can't wait to get out her favorite toys and stain the sheets when her pussy erupts.  I was just moaning and groaning and getting so close to cumming I wasn't even going to need more than a few seconds.

"You know I was going to order another toy today," she whispered as her fingertips slowed their pace.

"I was going to get one of those Hitachi wands and I wanted you to stroke yourself next to me as I used it the first time."

The wands were amazing.  I've seen girls use them in videos and they are mind blowing.  They can even get a man off.  I nodded and grunted in approval.

"I hate ordering things on my phone though.  Everything is so small.  I didn't want to order it at work either though so I used your laptop," her finger stopped over my balls and I froze.

My heart was beating faster.  I felt like I was sweating.  My cock nearly shriveled up in an instant.  She held the silence for what seemed like minutes.

"I never got around to ordering it though, do you know why?"  I shook my head no in the slightest manner possible.  It felt like I hadn't taken a breath in a long time.  I was more nervous than I had ever been in my life.

"I was going to google sex toys, hitachi wand but the search engine seemed to have saved a few of your search items.  Well a lot of your search items," her fingernail started to trace down my balls at an extremely slow pace.

"So I got even more interested and opened your search history and it was very, very eye-opening," she gripped my balls tight and I winced.  I didn't want to say anything.  I wanted to run out of the room but I felt paralyzed.

My balls slid out of her grip as she ran her hand back up and wrapped around my now limp dick.  She began to lazily stroke it.

"There were some things in that history that I had never even realized were a thing.  Sexual denial?  Sissification?  Feminization?  Male Chastity?  Humiliation?"  She let out a laugh and I felt my cock twitch slightly.

"You know I did end up buying something though.  Not for me.  Well it's for both of us," she leaned over and grabbed something under her pillow and dropped it on me.  I looked down and picked it up.

"Now you don't have to imagine what it feels like anymore.  Let's put it on."

She didn't even wait.  She picked up the male chastity device, the cock cage, and sat up on her knees next to me.  I tried to prop myself up and talk but she put her palm on my chest and shoved me back down forcefully.  I could have overpowered her and slid off the bed but I didn't.  I just laid there as she took over.

"I looked at the instructions already.  I wanted to make sure it went on without a hitch," she smiled up at me and slipped the small, metallic device over my flaccid penis.

It went in perfectly.  She had chosen a basic model but one that I've seen a lot.  It always looked better than the full covered plastic looking devices.  This was just metal bars that looked like your cock was locked up in a prison cell.  It was really fitting in a way.  The coldness of the metal made me jump and gasp.  It almost felt as if she had kept it in the refrigerator or something for an extra effect.  Probably to get my cock to shrink if I was still hard when she tried to put it on.

Her delicate, slim fingers made sure everything was in place.  She moved my junk around left and right to see if it was all fitting then grabbed the small pad lock and slipped it through.  With a quick look in my eyes and a smile on her face she snapped the lock shut and gave it a tug.  It wasn't moving.

She let out a gleeful squeak and gave the entire device a tug towards her to try and slide it off.  It didn't budge but my hips moved with it as it strained everything in me while she tugged on it.

"Ah!"  I yelped and she laughed.

"Good!  It's in place.  How does it feel?"  Her eyes were lit up.

"It uh-, I guess it feels alright.  I don't know," I wasn't sure what she was expecting me to say.

"I guess it feels a little heavier than usual."

She snorted a laugh, "well then, now lets see if it really works."

She got an evil smirk on her face and ripped her top off.  There was no bra underneath.  She rolled onto her back and pulled her pants down her legs to reveal no panties.  The smile on her face was bright and devilish as she crawled over top of me and straddled my waist with her cunt nearly right on top of my cock cage.

Her hips started rolling and gyrating over top of me and she reached her hand down and spread her lips apart trying to slide the device inside.

"Doesn't seem like it's going to fit.  How does it feel now?"  She smiled up at me.

I shook my head no for some reason, "it uh, its a little snug now."

My breathing was getting heavier as I felt her warmth so close to me.  My balls were near her ass and my caged cock was so close to her warm, wet pussy.  She leaned forward and kissed me wildly.  Her tongue probed my mouth.  She was pushing me further and further and my cock was trying to get harder but it couldn't.  I started to wince and mutter things.

"I can't," I thrashed my head one way in exasperation and she continued bucking her hips.

"Ungh, I just-, Mmm, please," my voice was getting desperate.

She whispered, "come on baby, don't you want to fuck me?  Put it in me.  Fuck my pussy.  Why won't you fuck me?  Please.  Come on.  Don't you love my pussy anymore?  You would put your cock in me if you really wanted to fuck me.  Do you not like pussy?"

My breathing was stuttered and sporadic.  I was in pain.  My cock was trying to get completely hard and it was pressed up against the limits of the cage.  The only choice I had was to push her off of me.  This hot, sexy woman begging me to fuck her and I had to make her stop.

"God please no!  I can't!  Fuck.  Fuck fuck fuck.  Fuck.  Nnnnnmmmm, fuck.  I can't," I closed my thighs tight together and whined and groaned in frustration.

She reached her hand over and cradled my balls, rubbing her wrist into them, "come on baby, what's wrong?  Fuck me.  Please.  Let me feel you cum inside of my pussy.  Don't you want to fuck me?"

Her coercing was making everything so much worse.  It was painful beyond focus and I grabbed her wrist and tossed it back to her.

"No!  Fuck no!  Jesus," I exclaimed in her direction.

She replied almost immediately as if she was expecting it, "you don't want to fuck me then?  Mmm, that's too bad.  I guess I'll have to find someone else who will from now on then."

I grabbed her wrist and yanked her back to me, "no you don't.  Get back here.  Get the key, take this thing off and I'll fuck you more than you've ever been fucked before."

The smile on her face turned wicked as she heard my words.

"I'm sorry, I can't do that baby."

"Why not?!"  I said in an exasperated voice.

"Because, I hid the key somewhere else.  It's not here.  You don't get to know where it is.  You don't get to know when I'll unlock that little tiny dick of yours.  We're going to play a game and you don't get to know when it ends."

She looked excited.  Her eyes were shining.  The smile on her face was from ear to ear.  I didn't even know what to say.

"I looked through your history and it was very interesting.  Now I'm going to give you a gift and we're going to play out some of it.  All of it.  We'll see if I get bored or not.  Either way you're going to do whatever I say or you're not getting that key back.  We're going to make you a good boy.  You're going to do whatever I want, whenever I want and you're going to like it.  Now be a good caged bitch and put your face between my legs until I tell you you're done."

She slipped onto her back, spread her legs and patted her thighs.  She head nodded for me and then snapped her fingers.

"Now.  You don't want to know what happens when I have to ask twice."]

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