Sissification 101: Ch. 03

Thereafter we ate our dessert in silence... the only noise being a faint buzzing in my pussy... that even I could barely hear, and I wasn't sure if Joan could hear it at all.

We finished the cheesecake, I paid the bill, and we strolled out hand in hand... the buzzing suddenly stopping... which was both good and bad. I was really enjoying the teasing pleasure in my nether region, but I wasn't sure I wanted to walk through downtown in a state of frustrated horniness.

The theatre was two blocks away, so we walked. Just enjoying the evening air and each other's company.

We entered the theatre.

We stood in line together chatting away about whatever, to purchase glasses of wine.

We chatted.

The buzzing started up again.

She smiled, as she pulled out the remote, "I really like this thing. And especially the look on your face whenever I exert my power."

"I bet you do," I said.

She shut it off again. "Just a tease for later."

"I'm not sure I can take much more of that kind of teasing."

"Too bad, you'd better get used to it," she said, sipping on her wine.

Three hours later, we left the theatre following a wonderful show. Humming soul music, we went to Joan's car to fetch a travel bag she insisted was vital to the rest of the night, we summoned an Uber, both of us having had a couple more drinks than the law would allow before driving.

Joan, not too concerned about the driver, or perhaps deciding to give him a drive to remember, said, "God, I can't wait to get to your place and really fuck the shit out of you."

"Don't you know I'm more than just a piece of meat?" I joked, not any softer than she'd been.

"You are?" she asked as if this was news, as she gave me a surreptitious wink.

"Yes, I have feelings too," I pointed out.

"No worries, you'll be feeling me," she countered, her meaning lost to the Uber driver but not to me.

Deciding to enhance the driver's shock I said, "I can't wait for you to take my virginity, dear." He would likely think, Who is this thirty-something Asian virgin?

Although that wouldn't last long as Joan clarified, "You see, Howard," that was the driver's name, "I'm pegging him for the first time once we get back to his place."

"Oh," the driver said, clearly shocked and a little uncomfortable.

"God, I'd suck your tiny dick right now if it wasn't caged," she added.

"Up to you; you're the one with the key," I pointed out, the idea of her lips wrapped around my clitty making my cage rattle, a bit more figuratively this time.

"Oh shit," she said.

"What?" I said, her tone worrying me.

"I have no idea where I put it!"

"Really?" I asked, that scaring me a little. I liked the cage. I liked the discipline. I liked giving her all the power. But I couldn't fathom her never being able to take it off me even if she wanted to.

She didn't speak for a few seconds, long enough for my stress to grow alarmingly, before she laughed, "It's all right sweetie, I have the key."

"I hate you!"

"I thought you w-w-oved me," she whined, suddenly all baby talk.

"I can't stay mad at you," I said.

"Because you w-w-ove me?" she asked, pouting. God, she even pouted sexily.

"A little," I answered.

"Onwy a widdle?" she carried on with her spoiled little girl act. "Just wike your clitty is widdle?"

"Oh, that widdle thing? Yes, I love you much more than that," I reassured my widdle girl.

"Thank God," she said, before adding in a normal voice as Howard pulled up to my house, "In case you didn't catch our drift Howard, my boyfriend's dick is really small."

He stopped the car without comment, but I did think I saw an embarrassed cringe.

"Her strap-on is a lot bigger than my clitty," I added.

"And you're about to take it up your tight virgin cunt."

"And I can't wait. Thanks for the ride, Howard," I said.

"But now my boyfriend's about to really go for a ride," she added.

"Have a good night, you two," Howard said, clearly discomfited by the entire situation, and happy to see our backs.

We got out of the car, went directly up to my bedroom, and she pushed me onto the bed.

I complained playfully, "Hey, I think the man is supposed to do that."

She refuted, "No, the Mistress does everything, and the sissy gets things done to her. Until the Mistress changes her mind, of course."

"Yes, Mistress," I agreed, as she got onto the bed with me and began kissing me.

And right before the wildness that was about to occur... dominant sex... sodomy... my sissification getting enhanced... we shared some tender intimacy.

We kissed.

Nothing more, nothing less... for a good ten minutes.

No talking.

No groping.

Just our lips pressing together and our tongues dancing with each other. Oh yes, and sighs. There was lots of sighing.

She broke the kiss... I would have remained in this moment of sweet tenderness forever... although I was really dying to see what was under her dress and to cross my next frontier of sissihood (I know that's not a word; perhaps it should be).

She looked into my eyes... with love and caring. "Last chance to change your mind."

"Do you want to change your mind?" I asked, hoping her answer was no. I'd found my soulmate, and I hoped she still wanted to explore all the devious fucked up kink I'd only ever dreamed of doing.

"Not at all," she said. "But I want to make sure you're one hundred percent certain you want to do this. Once we go through with it, we won't be able to unsodomize you afterwards."

"But I have a pussy, you've said it yourself," I pointed out with a smile. "And you can't sodomize a pussy."

"Okay then," she smiled back. "But my point is the same, just in different words. You can only have your virginity taken once."

"Agreed. And since you ask, I'm one hundred percent certain I want to lose it to you," I said. Considering that this discussion was about a girl about to ass fuck a guy... not to mention about a woman transforming a man's masculinity into femininity, it was an incredibly romantic one, and I wanted to make that very clear. "Bottom line Mistress: I love you, and I want to do everything with you, and to do everything I can to please you, for the rest of our lives."

"Wow! I really felt that. You're the sweetest man I've ever met," she professed sincerely.

"And you're perfection," I replied.

She leaned in and kissed me again.

This time for just a few seconds before she broke the kiss again, got off the bed and said, "Then I guess it's clear that your commitment to this course of action is totally settled, and therefore so is mine. So going forward..." and she jumped back into a playful mode... "you want to see what I bought just for this special occasion?"

"Yes, I do," I said with bated breath.

"I'll be back in a minute," she said. "Why don't you get out of that misleading man costume? For the rest of the night you're to be who you really are... a sissy slut."

"Yes, Mistress," I replied, as she grabbed the travel bag we'd collected from her car and left the room.

I got undressed, as intense high-speed vibrations resumed in my cunt.

Not getting completely undressed, of course; I left on all my wedding night attire.

White lingerie.

With white stockings attached.

Looking into the mirror, I looked incredibly feminine.

I also looked incredibly sexy. (Which isn't as conceited as it might sound. I'd never seen myself looking anything like this before, and I was blown away!)

My overly feminine body, which had always been my second largest insecurity (after the size of my penis), had suddenly become an asset.

I admired myself in the mirror, wondered if perhaps I should begin painting my toenails, and then I began posing for myself. I was bending over to check out my ass, when Joan walked in.

She startled me by asking out of the blue, "Admiring your girlish beauty, my sissy slut?"

I turned around about to quip something, but instead I froze and gasped. I'd expected that she'd been wearing something sexy underneath her dress all evening, but nothing could have possibly prepared me for what I was suddenly staring at.

"Like?" she asked, as she posed for me in a black leather teddy (although that's a very inadequate descriptor for a dominatrix goddess outfit), which was attached to black stockings, and black five-inch-heeled boots that went up to her thighs. She undoubtably looked like a Mistress.

"You look unbelievable," I moaned, helpless from lust, unable to remove my stare from the entire package that was Joan. She looked radiant, and equally dominant. The strap-on cock pointing directly at me completed the ensemble, making her into dominance personified.

"I know I do," she said, as she turned around to show off the seams going down both legs. (If your Mistress has a seam down the back of her stocking, you know she means business.)

"Wow, just wow," I said, as my clitty desperately tried to break through the cage that was keeping her down.

"Like my new necklace?" she asked, turning back around to show it to me.

I looked at it and noticed that besides it being a very nice delicate gold chain... it also had a key suspended from it... assumedly my cage key.

I said, "Very nice."

"I thought this would be a convenient place to keep it, so I could lock or unlock your cage anytime and anyplace.'

"Good idea," I said, desperately hoping I'd be uncaged tonight.

"So since you're dying for me to unlock your cage," she said, reading my mind again but probably not needing much clairvoyance this time to do so, "you have a task to perform. This cock isn't going to suck itself," she hinted broadly.

I began to walk towards her, eager to take her cock in my mouth, but she stopped me in my tracks. "Nope! Crawl, sissy."

"Yes, Mistress," I obeyed, having read those exact words many times in a variety of domination stories by silkstockingslover. Usually the statement was made by a dominant woman addressing a submissive woman; and at this moment, I realized, the same was true here.

Joan was the dominant female.

I was the submissive female.

Joan was going to train me to be a submissive sissy slut.

I was going to obey without hesitation every order given me by my dominant Mistress.

I lowered myself to my knees and then, like a good pet, I crawled the few feet to my Goddess of a Mistress.

"You like being on all fours, Erica?" she asked as, with my hands still on the carpet, I sat on my haunches before her.

"I do indeed, Mistress," I replied, bending down and kissing her boot.

"Nicely done, except that I require balance at all times. Kiss the other one, too."

I did.

"Now turn around, I want to see that pussy," she ordered.

"Yes, Mistress," I obeyed, turning around and showcasing my arched back and feminine ass proudly, posed as if I were a top competitor in the annual Westminster Kennel Club Dog Show in New York City.

"Reach back and spread those cheeks nice and wide, so I can get a really good look at that pussy," she ordered.

I had to abandon my championship bitch pose and far less gracefully, I rested my head on the carpet so I could do as she instructed.

"Pull those ass cheeks apart wider," she ordered.

I pulled them as far apart as I could possibly go.

"Shit, I think we'll have to manicure those nails one day soon," she observed.

"I was already thinking of painting my toes," I admitted, keeping my ass cheeks wide.

"Oh, we'll be doing your fingernails too," she promised.

"Yes, Mistress," I said, a little self-conscious about having my fingers painted, and then going out in public.

"Now come and get this cock nice and ready for your virgin pussy," she ordered.

Part of me still couldn't believe this was happening... my greatest fantasies coming true like this... it still seemed unreal... like the best, and also longest, dream ever.

Yet my caged clitty, my all-white lingerie, plus my girlfriend's black dominant attire all made it pretty clear. This wasn't a dream.

I knelt before her and took the black (of course) cock in my hand. "What a great cock," I admired, even though it was quite small for a black one.

Six Inches.

And thin.

"It's just a beginner cock," she said. "Your pussy couldn't possibly take my two bigger black cocks," she said and paused for a moment, "yet."

As I stroked the cock I said, "I can't wait to be able to take every big black cock you can find into my needy cunt."

"All in good time," she said, as I licked the shaft up and down... something I liked having done to me.

I did this for a few seconds before she ordered, "Now suck it, slut."

"Yes, Mistress," I replied, getting a rush of adrenaline every time she gave me an order... my clitty continuing desperately to try and salute this beautiful goddess... pleasure denied for the past few days really driving my core existence crazy.

I opened my mouth and took the delicious cock in my mouth, as the vibrations again resumed inside me, this time more intensely than ever before. "Oh fuck," I moaned just before I wrapped my lips around Joan's cock.

I bobbed slowly on the cock, still getting used to the strange yet natural feeling of having a cock in my mouth... albeit only a plastic one.

God, I really wondered what a real cock would feel like between my lips... deep inside my mouth.

"A sissy slut bobs on a cock, she doesn't fucking make love to it," she scolded.

I followed her instructions as I began to bob on the cock, determined to take all six inches in my mouth. I wanted to be a great cock sucker, especially when the inevitable opportunity to suck Carter's big black cock, or any other big black cock, was offered to me.

"That's better," she encouraged, moaning softly.

Was she getting turned on from watching me suck her cock as much as I was stimulated from sucking it?

I had four inches going easily in and out of my mouth, and I tried taking a little bit more with each forward bob. I was determined, come hell or high water, to take the entire six inches into my mouth.

"That's it, keep taking more and more between those pretty cock-sucking lips," she encouraged, constantly reading my mind.

The strange compliments continued enhancing my inner pleasure and lust, even as my outer pleasure was still completely restrained by the cage.

A dozen bobs and I had five inches in my mouth... which gave me a rush of excitement as I got closer to deep throating all six inches.

"Getting closer, faggot," she said from above me, that term always seeming harsher than others.

I was a sissy... hard to argue, as I loved dressing up.

I was a cuckold... I definitely wanted to watch Joan getting fucked by BBC. I wanted her to have the massive orgasms from a real dick that I couldn't give her physically, but that I certainly could assist her in reaching with others.

I was a cock sucker... well, I wanted to be. I already had a plastic cock in my mouth in part to practice with, and I wanted nothing more than eventually to suck to completion a BBC.

I also wanted to taste a load of cum.

I wanted to take a facial.

I also was curious to get fucked... today by Joan's strap-on... another day by a BBC.

Yet, I wasn't sure I was a faggot. In fact, I probably wasn't one, since I got turned on by women. I didn't find men sexually attractive... just cock... and more accurately, just black cock.

I didn't want to kiss a man.

I didn't want to hold a man's hand.

I most certainly didn't want to date a man.

Could you imagine me flirting with Carter? I think not.

Could you imagine Carter flirting with me? That would be just plain wrong.

I just wanted to suck and get fucked by BBC.

As I pondered all this... which in essence was just semantics... just boxes... just labels that oversimplified who people were... And who was I? I was who I was today, while tomorrow I might be something a bit more or less... as simple as that.

I took the final inch of my practice cock in my mouth.

I felt like I had won the Stanley Cup.

"Good girl," Joan moaned, congratulating me on my first ever deep throat. Sure it was only six inches, but after taking all of it for the first few times, I could now take it easily, without gagging at all, which was thrilling! Hopefully I would soon have larger... and actual... cocks in my mouth and down my throat.

Joan pulled out and asked, "What do you want, Erica?"

"I want your cock, Mistress," I responded instantly... my mind now switched to sexual submission cruise control.

"Where?" she asked, tapping my lips with her cock.

"In my cock sucker mouth, or if you would be so kind... in my virgin ass," I replied forthrightly, dying to feel the pleasure and pain of anal sex... the constant buzzing having been driving me wild ever since Joan had left to get changed, and had then returned to play.

"In your what?" she interrogated, tracing my lips with her cock.

"Sorry, silly me," I apologized, having briefly forgotten my new gender. "In my pussy, my cunt; I desperately want to feel your black cock pounding my virgin pussy."

"Better," she approved, as she snapped her fingers and pointed to the bed.

I crawled, like an obedient puppy, on all fours to my bed.

She ordered, "Take off your panties."

"Yes, Mistress," I responded, starting to stand up.

"But do so while on all fours," she ordered.

"Of course, Mistress," I nodded, thinking this would be a lot more challenging. I moved my left hand to my panties and tugged them down, but after only an inch or so they were caught on the cage.

I did the same on the other side, more forward than to the right this time, and with three yanks, the panties had managed to get past the cage, although it hurt like hell while they did.

It then took me another thirty seconds to slowly pull the panties down side to side, bit by bit, to my knees.

I raised my right knee and pulled the panties over it.

I did the same thing with my left knee.

After that it was easy: I just used my right hand to sweep my panties down my calves, over my feet, and off.

It literally was a workout; I was sweating afterwards.

"Good girl," she chuckled, clearly amused by all my tussles.

"Thank you, Mistress," I said, realizing I was also slightly out of breath.

"Climb onto the bed and roll onto your back," she said. "I need to see your caged clitty."

"Yes, Mistress," I replied, crawling onto the bed and then onto my back, the vibrations in my pussy and clitty still continuing relentlessly, although now my cage was swinging around whenever I moved.

"How has wearing a cage been for you?" she asked, as she crawled between my legs.

"Intense," I answered, that one-word answer pretty much encapsulating every feeling that had come with wearing the restrictive device.

Intensely humiliating... as I allowed Joan to take control over my manhood.

Intensely frustrating... as my clitty was constantly stimulated, yet ignored.

Intensely stimulating... I'd been constantly horny and on edge.

Intensely consuming... the cage had taken complete control of my attention, making it very difficult to focus on anything else.

Intensely life-altering... in one wild week, everything had changed.

She smiled as she cupped my caged dick, "The dear thing really is small."

"I know," I said, her humiliating words enhancing the pleasure consuming me.

"I mean ridiculously small," she said, bending down to get an up close and personal look at my pathetic little caged clitty.

"I know," I whispered, my heart filling with shame.

"And yet so easily excitable," she said, as she massaged my clitty through the cage, and then moved her finger up to my lips.

I sucked a very small amount of pre-cum off her fingers. I wondered how much leakage I'd had today... the constant stimulation throughout the day as my clitty begged for the attention and release the cage refused to allow.