Showing posts with label sissy. Show all posts
Showing posts with label sissy. Show all posts

Blue light special



I was just about to call it quits on our #Girlsnight when a soft blue light shone before us down the bustling alleyway. I held his hand softly as we approached the window.

His perfect green eyes danced with glee.

"This is the one Josy," I whispered as I put my hand on the doorknob to push open. He just nodded obediently, silent with anticipation. I knew to get him into the sissy mindset before any play it was best to refer to him as his sissy name.

He had been making so many big decisions on his own and processing so much during our forced time apart. I knew it had been wearing on him. He had managed to meet me in Amsterdam, I figured not only was it our anniversary, I also knew this was a huge fantasy of his and I wanted him to remember who was in control. I wanted him to switch off and just do as told. A mindless toy.

'I don't do fantasies, I make plans' I could hear myself telling him two years ago to the day. I really believed that. Anything I thought was hot, I sought out to do, not fantasize about. And that always made it that much sweeter for me.

So when I walked into the tiny, dingy, dim lit glassed room with my pantied, sissy fiance whom I'd not seen for months, on our two year anniversary, with an eye-catching and slightly dominant TV I couldn't resist.

"How much for him to suck you?" I asked the prostitute as if I'd done this a hundred times.

She looked him up and down slowly. It seemed she liked what she saw.

"It'll be $100 for him."

She turned her heavily made up eyes to me and lingered. Her breasts heaved beneath her black, tight corset top.

"Extra 50 if you wanna join."

I instructed my girl to go get cash. He asked how much he should get and I replied, "You know how much," and off he went into the noisy streets of Amsterdam. It didn't truly hit me that we were about to partake in the world's oldest profession until further reflection. It was history. It was novel. And it was going to be fucking hot.

In the six minutes he was gone to retrieve currency Melinda and I talked about politics, the locals, our desires and our dynamic. Like most she was fascinated by the Femdom concept and asked a few questions.

And he just does what you say?
He likes pain? Humiliation?
Do you fuck him?


All good questions that I answered politely and when my toy came back, wide eyed, and then he was ordered to strip by Melinda. He did as told and then I stepped in admiring my view. I placed my hand out waiting as I slid the belt from his waist and through the loops with ease and held it tightly.

"Get down on your knees and start sucking slut," I ordered as I shoved his head in her general groin area.

The professional reached for a condom and waited by rock hard. It was an cock that demanded attention. My good sissy did as told and gobbled up the stranger in her little mouth like it was her favorite cock. She moaned deeply thrusting her tight little ass in the air.

I slapped the target with her own belt and degraded her verbally.

"Look at my slut moaning for cock," I said.

Her eyes looked up at me, any hint of innocence leaving them in a blink and then they bulged with reflex.

"Suck deeper. Open your mouth wider!" Melinda shouted.

I watched Josy struggle to accommodate more meat so I grabbed her by the hair and aided aggressively.

"Don't disappoint Mistress," I leaned in and whispered, a handful of her locks still intertwined in my fingers.

"Suck this cock like you want it. Show me you need it," I said feeling my own panties starting to moisten.

Josy, like the good girl she was, bowed lower and took more of the large throbbing member in her mouth. I reached for the woman's balls and held them in my hand and used it to stroke upward to give Josy more.

She gagged as her head was held in place. Melinda threw her badly wigged head back and laughed a throaty laugh. Then I reached back and started spanking Josy's ass until it was my favorite shade of red. I could feel my slut's tiny cock bounce against the leather bed. It was at more than full attention. I slapped it down and then again when it bounced back in an instant. She didn't flinch like she normally did, her mouth was full, her clitty was hard and she was deep in sub space. It was written all over her glazed eyes.

"You're not going to be using this," I teased as I ordered her to sit up.

I looked her in the eyes as I reached down to remove my soaking panties.

"Now Mistress is going to use this cock."

Josy stared at me with a gaped mouth and doe eyes and simply said, 'Yes, Mistress.'

This delighted the cross dresser who offered me a place on the bed. I stuffed my panties in my future sissy husband's mouth and placed my head under his pathetic penis. She wasted no time spreading me open and getting to work.

Her finger work wasn't refined but it got the job done causing me to twitch and get wetter. She sniffed the air and looked at Josy....

"I'm going to fuck your girlfriend," she said bluntly.

"I'm going to fuck her good. Are you ready?"

She asked this without really waiting for either of us and as she pressed her fat, thick headed, cock against my hole. It was all I could do to not explode. I was wet and she was putting my ankles above my head. Josy was directed to hold each one in place and was holding on with determination.

I imagine she was steadying herself in the surreal scene that was taking place before her.

This gave our lady of the evening a great view, two free hands, and placed me in a completely vaginally exposed position. I had three hands on my breasts and cock in mouth, and one in my pussy. This encounter was feeding my inner whore on so many levels it didn't take much for me to start squealing and struggling to hold my own personal ecstasy back.

"You see that? She like me FUCKING her," I heard her broken English with my eyes closed and a hard pounding to my pussy followed.

I began jeering Josy telling her what a naughty girl she was. 

"You're so disgusting Josy, you slut. You won't be fucking me like this."

Melinda spit on my sissy's chest at random intervals while fucking me hard and deep just keeping me on the edge. I could feel tiny sissy clit still flexing in my mouth so I changed back to the original position with Josy on her knees. She spit out the panties and resumed greedily sucking.

This time I ordered her, "No coming. No coming!' 

"No coming for you stupid," the sex worker chimed in as her hands slid behind Josy's cock and balls for a fondle.

I watched my sissy show me just how turned she was and how dirty she'd be for me. I could tell she was enjoying herself and wanting to pleasure me by just offering herself for use. The consensual desperation that was begging behind her eyes was dazzling and I spanked her harder until my hand stung. Melinda copied me on the other cheek.

I had a feeling that the prostitutes in Amsterdam weren't use to having an interracial, Femdom, sissy based intercontinental couple walk through their doors as I watched genuine excitement  and arousal on the professional's face. I let the two of them continue on their own for a few minutes while I got redressed.

"Have you had enough cock?" I pulled Josy's face from the still hard bobbing knob. She nodded slowly. I could tell she wasn't sure if she had either but I pulled her off anyway.

"You've had enough, now say thank you," I ordered.

Josy complied just as I added, "And kiss the cock." She did this graciously as well.

We washed our hands and my Josy girl put back on his panties, then the rest of his garments. We were glowing with an aura of sexual conquest.

Just as we were about to leave Melinda looked in a mirror and re-applied her make-up getting ready for her next customer.

"Very nice pussy. Almost make me come," she said to no one in particular very matter of factly.

"Yes, it is a nice pussy," Josy shyly agreed as we smiled and left.

I don't think I'll ever look at a blue neon light the same.
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Was it ever really a question?



Puppy will soon be under a different type of lock and key. He has no idea what he's signed up for. #ISaidYes





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Dear Diary #1

**Trigger warning: This is a re-telling of an intense domestic violence roleplay we engaged in. Please do not read any further if you may be triggered by things falling under that umbrella. Thank you.**





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Sissy sluts unite




Earlier in the evening Mistress informed me that we would be having a play date with another sissy. I was initially surprised and a little nervous but as it got closer to leaving to go to the dungeon, I got more and more excited. I was so excited that I actually got dressed in my full sissy wear before leaving, forgetting that for the first couple of hours of the night I was a demo bottom at a cbt station, and my Josy persona was going to have to wait. I literally had to change in the car back to my boy clothes while she drove to the event. With Movember behind us I realized, it had a been a while since I had dressed up and I was excited to be my Josy self again.


After two hours of kicking, kneeing, crushing, caning and for the first time ever, the excruciating feeling of BenGay, my sissy balls were aching and I was happy have them once again protected by my chastity cage, where I know my sissy clit belongs. The other sissy that Mistress had organised our play date with had been popping by to talk/flirt with us all night. Mistress had locked her up for the evening just for fun and I had to admit, despite not often finding other sissies hugely attractive, I really did think Chelsea was cute, and looked wonderful. Was I crushing? Definitely and was excited for whatever Mistress had planned.


I was told to change into my maids uniform and as always I felt so very pretty in my petticoat, pink panties, and pristine white lacy gloves. I got such wonderful and positive feedback as Mistress paraded me around on her collar and leash. The other sissy found us and Miss ordered Chelsea to change into her maid uniform and she came back looking very slutty. My maid's uniform is prim and proper. If it wasn't I'd be too distracting when Mistress is trying to work while I'm cleaning.


We both sat at her feet and Mistress knew we would do anything she wanted or needed. One thing I definitely liked was that like me, Chelsea didn't seem to be doing this for humiliation purposes, but purely because it was fun, and incredibly hot.


We were ordered to head over to a spanking bench and link hands facing each other. We looked each other in the eyes and Mistress spanked us, with our skirts pulled up. Mistress told us we were sisters. Yay! Finally a sissy sister to share the spankings with! We took our spankings before Mistress had us practice some submissive positions. This is always about power, control, and obedience for Mistress so I know she enjoyed having two sissy girls kneeling at her, literally worshipping the ground she walked on.


"Josy, you have one chance to ask Chelsea the question I know you want to ask and if you ask the wrong one, you will get 100 spankings right here!"


I'm never one to turn down spankings but I thought about my two hour tear inducing spanking less than 24 hours previously. Mistress and Marissa had bruised my ass, I wasn't sure I should be cheeky and get it wrong.


I timidly looked the taller, more curvaceous sissy in eyes again and asked... 


"Chelsea, may I please suck your cock?"


I hoped she would say yes and moments later my wish was granted! I was on my knees as I begged Chelsea and Mistress for cock. It didn't take long before she was hard and ready. I slid the condom down her cock (always safety first) and began sucking. Her cock was a nice size, and I was able to take it all in my wet mouth. Mistress says practice makes perfect and I was enjoy practicing deepthroating for her pleasure.


My head was held in place but there was little gagging. I made sure to suck cock just like Mistress had taught me, and I hoped I could make her cum. Unfortuantely Mistress likes to tease me and keep me wanting so only allowed 5 minutes of sucking. I knew these minutes would go toward my 169 minutes of sissy cock sucking training (69 minutes left!) I thanked Chelsea before kissing her shoes as Mistress ordered and looked on proudly.


We cleaned up, I got changed and headed back out into the real world. I thought that 4 am was bedtime after such an eventful weekend but Mistress was obviously still feeling excited as she allowed me to worship her pussy before using the dildo to give her two powerful orgasms. I feel asleep next to her, feeling like a well used slut.


She mentioned something about having an 11 inch cock give me a facial later tonight as she drifted off to sleep...


What have I gotten my little sissy self into?!


Sissy Josy
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A sissy's request



My Queen, 

Please allow your slut to have a ruined orgasm tonight. I am so desperate and needy after a week of chastity and spending every day with you. 


I crave your touch around my tiny cock and any kind of release you will allow. I know my orgasm is of no interest or use to you, but I beg and plead that you will allow even the most pathetic type. I beg that you will let me dribble out for your amusement and my pleasure. I will of course clean up whatever mess there is however you wish. 

I know that you already do so much for me, but please Mistress, please allow me a ruined orgasm tonight, I promise to be a good sissy and go straight back into chastity after. 

-Your sissy slut 

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Dude looks like a lady

Congressman: I missed you.

Miss L: You only think you did.

CM: No, really I did.

ML: Prove it.

CM: Ha, you love having me at your mercy don't you?

ML: I have to admit it does get me a bit hot. Even just thinking about it gets me tingly.

CM: Oh...is that because you know to the outside world I would be a far cry from being considered submissive?

ML: Yes. And  I know behind closed doors I can dress you up like the shameless sissy you are and make you beg for me.

CM: *Blush* Yes Miss L. I would beg for anything from you.

ML: Good. Prove it. Beg to dress up in your pretty dress for me. Get on voice chat, I want to hear you whimper for it.

CM: Yes Miss L

He proceeded to get on voice chat and beg to wear the dress I liked to see his legs in. He was breathy, and spoke carefully. When I commanded a whimper he did so without hesitation. Hearing him moan and whimper made me want to dominate him even more.

ML: You're such a good boy for me sometimes.

CM: Haha I try to be Miss L. I want to be your good boy and yours only. Would you like for me to put on the dress now?


ML: Yes, turn on your cam and strip for me, then I want you to open the curtains in the room and put on the dress.

CM: The curtains? My neighbors can see in from this side of the building.

ML: ...Your point being?

CM: Yes Miss L, I will do as I am told.

With his webcam on he did exactly as I instructed. He took the slowest steps possible to the window and opened the curtains a bit.

ML: Congress boy, I want to see those curtains open wider. Just the way you were spread for me last time we were together.

He came back to the camera with a bit more red on his cheeks and a small smirk on his lips but opened them wider. I watched as he left the room and returned with his dress. He put on the stockings, his dress, a very nice wig and then he pranced over to the camera. It was quite sexy to watch the transformation.

CM: How does this look? Does Miss L approve?

ML: Turn around

He spun around causing his dress ruffles to bounce a bit.


ML: You look delightful! Now I want to see my good by act naughty.

He covered his mouth with his hand (like a proper lady), laughed and then curtseyed.


CM: Whatever you wish my Mistress
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Up, up, and away

Even while jet-setting writer sub continues to be a good little panty boy for his Mistress...

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TGIF

Writer sub is becoming the perfect little sissy, wouldn't you say? I think I'll officially be changing Friday to my favorite day of the week haha. Enjoy the view!

 

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