Taken Too Far Pt. 01

Story Info
A closet sissy meets a master in rush hour.
1.6k words
4.44
41.9k
48

Part 1 of the 2 part series

Updated 06/09/2023
Created 06/23/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic LiteroticaĀ® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I had maybe taken it a little too far. It had started as it always does, a little light crossdressing at home. Then toys as well. Then wearing something a little extra under my boy clothes when I was grocery shopping. Then when I was at work. And that leads me to my current situation. On the outside, jeans, t-shirt ā€“ normal enough. Underneath though...

It was Friday, and I was coming back from work. As had become my routine, I was wearing, underneath my normal work clothes, a silky black thong, and a lacy garter dress with stockings. All black, all carefully hidden under my outerwear. I was hairless from my eyebrows down. My toes were painted hot pink, which was also the colour of my chastity cage, which I had kept on for 4 days now, starting with Monday morning. Inside my tight, virgin ass was a princess plug, a jewelled butt plug that kept my ass full and my locked cock leaking slightly. The very attractive women in the office also helped with that.

I was a straight guy who had gotten into crossdressing, followed by chastity. No one knew of my secret kinks, and I aimed to keep it that way, even as I kept risking being found out by wearing this stuff every day during work hours. I was careful though, and was happy to be heading home. I had even gone a step further today, and written messages on my body. "Never unlock" was above my locked cock. "Breed Me" was stamped around my navel, circling it, and "urinal" & "slut" on each of my inner thighs. All were fantasies I had been exploring via porn, but I'd never actually do them in real life. That was about to change.

I was riding the tube back from work, in my modest apartment in London. It was rush hour, unfortunately, so we were packed in like sardines. I was idly toying with the key to my chastity cage, kept on a cord around my neck. It was a simple luggage lock, but it did its job. And that's when I felt I slight pressure over my crotch. The thing about being locked in a chastity cage is that your dick can't feel a thing beyond the plastic. I hadn't really noticed the first time that his hand had brushed against the pink painted steel cage, the touch was so light. But he had. He had felt that hard cage and become curious. He looked me over, seeing me playing with the key, and a wicked smile formed on his face when he realised what I had on.

We were packed into a corner, so no one could really see anything below the shoulders. I had to crane my head slightly to even see what had pressed down on my groin. To my shock it was someone palming my cage, feeling around it. And then his fingers reached underneath and touched my exposed balls and I had to bite my lip at the electricity that sparked in me. Being caged and not orgasming for nearly 5 days would do that. I followed the hand up to the man on my left. To the right was the carriage wall, and in front of me was the end of the carriage, so no one could see what he was doing except him and I. My eyes went wide with fear as I saw the predatory grin on his face.

His hand came up, after slapping my crotch, almost making me buck and moan. He kept his palm outstretched and waited, expectantly, for me to give him something. I looked back, fearfully and saw his eyes indicate the key around my neck. It was fine, I thought, I had a spare at home, he can take this, enjoy the train ride, and by the time I got home I'd be free. I unsnapped the cord around my neck and handed it over. He pocketed the key, and then his other hand came out, snaking around my back. With my bag, I'm sure no one could see as he started exploring my ass.

"Got any plans today...?" he whispered to me. I nodded, stifling the sounds I wanted to make as he rubbed and squeezed my ass, trying to avoid him finding the plug.

"You should cancel them..." he told me, as his hand found the plug, and started tugging at it, and my eyes went wide.

"Please stop, not here..." I pleaded, not wanting the world to find out what was going on, and far too close to moaning like a bitch in heat if he continued.

"Sure, but then you have to do something for me. Unlock your phone, and hand it over." He commanded, taking his time in continuing to tease my asshole with the plug as he did. My mind, were it rational, should have said no, as this was a bad trade. But, turned on for 4 days, unable to have an erection, let alone cum, and now being toyed with, had kind of put me in a low drunken lust. I would do anything to make him stop teasing me, because I knew it wouldn't take much more before I started moaning.

I handed over my phone and tried to calm down, breathing deeply, as he started tapping away. It didn't take long for him to do whatever he was doing, and then he pocketed the phone.

"When's your stop?" he demanded.

"Next station" I replied, meekly, still calming down.

"Good, we need to make a stop on the way, but after that we're going to your place. And then you get your phone back." he commanded, making sure I knew the reason I couldn't run away as soon as we got out.

We exited together, him leading me down a side street, as he asked me questions, quietly.

"Who else knows?"

"No one."

"More toys at home?"

"Yes."

"Do you crossdress?"

"Yes, actually I..." I trailed off, not wanting to give him more information, but he'd already picked up on it.

"Actually what?" He commanded, stopping us in an empty alley. I turned to face him, blushing, my eyes downcast, and lifted my t-shirt. Underneath, the black lace of the garter belt became visible. He smiled that same predatory smile, and continued walking.

"More of that at home?"

"Yes." I whispered back.

We enter a hardware store, where he quickly grab the few items he wants. I notice a couple of things, duct tape, something slender and something in a blister pack, but can't make it out. We're out the door shortly as I lead him to my place. I keep trying to calm down but my heart is beating so fast, I'm not sure if out of fear, excitement or both. We enter and as he closes the door he immediately commands me with a single word.

"Strip"

I don't want to, the curtains are still open, but from where we are, no one can see us. And he already knows what I have on. I peel off my loose t-shirt and jeans, and then my trainers and socks. I stand before him wearing nothing but the garter dress, a thong and some stockings.

"Cancel whatever plans you have" he states, as he hands me back my phone. I start texting and don't see him take several photos of me as I stand there. As I'm texting he asks me "Do you have make-up? Heels?" I nod as I continue texting. When I finish he tells me to go put on the make-up and the heels, and let my hair down from the man-bun I currently have it in. I hesitate and ask him

"May I close the curtains first?" He looks at me and nods, that smile creeping back across his face. As I'm finishing the make-up, he asks for where the toys and clothes are kept, and I point him to a couple of bags. He looks through them, muttering in approval.

I stand up and walk over to him, teetering in my heels. Having done some of my best make-up work yet, I quietly announce that I'm finished. He looks me up and down and grunts. Then begins explaining.

"I know you're wondering what I plan to do to you, and given your attire, I'm sure it's something you'll enjoy. The important thing to know is that I own you, and you will do everything I tell you to do, or you will be punished. Now say it, and mean it."

I back away, unwilling to be taken this far.

"I've done everything you ask, please just leave now and I won't say anything..." I begin, my voice cracking. In a flash he throws me on the bed. I'm completely unbalanced on the heels and offer no resistance as I land on my stomach. He's on top of me, pulling my arms behind my back and binding them, I can only assume with the duct tape.

"Wrong answer, bitch" he whispers into my ear, before he licks my neck and flips me over. I try to resist, but I'm like a fish out of water, and with his weight on top of me, I can't move. I feel my panties being pulled aside, and then a clicking sound. He drops the luggage padlock and the key on top of me. My mind doesn't understand ā€“ this was his leverage wasn't it? Why remove it? And then I hear another click. He gets off me as I struggle to sit up, looking down at my crotch. My chastity cage is still there, but now with a heavy duty security padlock, the kind you can't easily break, not even with bolt cutters. I look up to see him taking more pictures of me, now entirely en femme. He puts the phone onto video mode and points it at me.

"Say it, and mean it"

There's silence for a moment and then I open my mouth

"You own me, and I will do everything you tell me to do."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
11 Comments
MichaelfantasiesMichaelfantasiesover 1 year ago

Very hot, but VERY scary situation. TOO scary for me! I've been a discreet cross dresser for years. Mosty panties and some lingerie under my guy clothes when I'm out. The chastity thing... That's also too scary for me! While it is a turn on to read about, I'm not ready for something like a chastity! I would have to trust the man I'm with that wants that. Do most men want their sissies / gurls to wear a chastity?

Other than that, I'm not sure I'm going to like where this story is going. In real life, a dominant man like that that and that situation would be terrifying for me!

AnonymousAnonymousalmost 5 years ago

I love it. Now where is the rest of it!

tommytietommytieabout 5 years ago
Wow, so good

I love what he has got himself into, and i hope he gets all that he deserves and more!

AnonymousAnonymousover 5 years ago
Me

Oh god Iā€™m so horny reading this, I wish I was the guy locked up and submitting to the stranger oh god this is so hot please continue the story

AnonymousAnonymousalmost 6 years ago
OH i like where this is going

Don't hold back, we all know he deserves it all.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Property of the Master Ch. 01Ā Caught in a girl's swimsuit and dominated.in Transgender & Crossdressers
Sissy Meets DaddyĀ A sissy loses her virginity.in Transgender & Crossdressers
A Slut is BornĀ Young man forced to be a womanin Transgender & Crossdressers
Sissy, HypnotizedĀ A night out results in triggers unleashed for this sissy.in Transgender & Crossdressers
Neighbors Sissy SonĀ Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
More Stories