Sissification 101: Ch. 01

It was so humiliating.

And so stimulating.

And it was also, as I was soon to discover, only the beginning.

I licked all my cum out, the cocktail of our mixed juices quite unique and tasty, as she moaned, "Eat your cum out of my cunt, my sexy sissy."

Her words brought forth the naturally submissive nature I'd hidden away for all these years, as I obeyed, aggressively attacking her pussy and retrieving every last drop of our cum.

"Yes, you cum eater," she moaned, sounding as turned on by what we were doing as I was. "Eat it all up, like a good little sissy."

I don't think she was referring to my tiny penis, or even my slim feminine frame, but I took it that way, which enhanced my transition to submissive sissy and her obedient slave. I replied, between licks, "I want to be a good submissive sissy for my strong, dominant woman."

"Mmmmmmm," she moaned and twitched as I flicked her clit, "I like that. And I can be that woman for you."

She grabbed the back of my head and began grinding her twat against my face, something she'd never done before. I licked as best as I could, until she came, and a fresh helping of her pussy juice splattered all over my face as she screamed, "Yes, my sissy slut, lick up my cunt cum!"

I loved the alliteration as I did just that, licking up as much of her pussy cum as I possibly could... a taste I'd always enjoyed, and now even more so, since it was a cocktail of our blended cum.

Once done, she smiled and said, "Well, I came here to surprise you, but I was the one in for a surprise."

"I'm so sorry," I apologized, still a little ashamed she'd caught me in such a humiliating situation.

"No, I'm thrilled I discovered your secrets," she said, her face actually looking thrilled.

"You are?"

"If we're going to work as a couple, and I want us to work as a couple, we can't keep any more secrets," she said.

"I didn't think you'd understand," I said. I added, serving up my own vulnerability to her, "I don't even understand."

"Understanding will come in time, especially without any more secrets. We all harbour sexual fantasies we don't live out, and that we repress," she explained, almost sounding like a clinical psychologist, even as she kept her legs parted to allow me an amazing view of her pussy, thus presenting a very different persona.

"Do you have any?" I asked.

"Of course," she nodded.

"What are they?" I asked.

"Well... and I'm only telling you this because my naughty little sissy will no longer hide away any secrets from me... I've always been curious about having sex with another woman," she said.

"I support that wholeheartedly," I said, perhaps a little too eagerly.

"Of course you do," she said, giving me a smirk.

"Just saying, I support you unconditionally," I said, with a smile.

"Good to know," she nodded. "And although I didn't realize it until I caught you with your pants down so to speak, and then listened to your fantasies and watched these videos with you, I think now I may have a few new fantasies."

"Like?" I asked curious to know what my humiliation and perversion could have triggered inside her.

"Well, being gangbanged by black dicks sure sounds like fun," she smiled.

"Oh my," I said, visualizing her with three black dicks filling all three of her holes... even though I'd not yet fucked her ass; I didn't even know if she was into that.

"Fucking your ass also sounds pretty fun," she added, looking at me as my tiny penis hardened again.

"You want to peg me?" I asked, that being one of my very biggest fantasies, yet one I'd never fathomed ever having a chance to fulfill.

"Very much so," she said, as her nylon-clad feet went to my cock. "Shall I get a strap-on cock and fuck your virgin asshole? Would you be up for that? Or rather, down?"

Hearing her say asshole was somehow even hotter than her amazing offer. While she rubbed her silky sheer feet on my throbbing clitty. I usually took a while to regroup after an orgasm, but this time I was already ready, and loaded for more.

I answered, gradually coming round to the idea that I no longer needed to see myself as pathetic when I wanted to be the fuckee instead of the fucker, "Yes."

"Yes, what?" she asked, just like dominants did in the many stories I'd often read by silkstockingslover... pushing the submissive deeper into complete obedience by insisting they spell out what they want.

"Yes please, I want my beautiful girlfriend to bend me over and fuck my virgin asshole with her store-bought cock, which will be much bigger than mine," I replied, making it sound as wicked as I possibly could, even going out of my way to degrade myself, as I described exactly how I imagined her doing it.

"That's so fucking hot, you good girl," she purred, as she rubbed my penis with both of her nylon-clad soles.

"This is too," I moaned, both loving my first-ever nylon foot job, and loving that she was turned on by the idea of pegging me.

"Well, today is a special day," she smiled, as she got off the desk and knelt before me.

"So true," I agreed.

"Stand up," she ordered.

I did. "What I thought I was coming here for was to celebrate our six months," she said.

"What? It's not our six-month anniversary," I said, as she took my penis in her mouth, able to deep throat me without any effort at all. It would be four months on Friday... I'd already booked us a table at the best restaurant in town to celebrate it.

"It's been six months today since the day we met," she pointed out.

"Oh," I moaned as she bobbed on my cock, and at the reality of how sweet she was. I did remember when I first met her. I'd first noticed her because, unlike every other woman in the office, she was wearing pantyhose. I fell in love with her legs even before I saw her face, and eventually I fell in love with the entire package.... something I planned to tell her on Friday. To my mind, my using the 'L' word should be delayed until the time when I really knew it without a doubt... which I'd concluded even before tonight was absolutely the case, and now that she was being so supportive of all the kinks I'd always considered my secret shame, I was one hundred and ten percent certain.

She bobbed on my cock, and within a couple dozen stokes, I was already beginning to feel my balls boiling... I could never last long inside Joan's amazing mouth.

Her hands moved to my ass and gave it a squeeze, which she'd often done before, but this time I felt a finger against my ass, and while never losing the rhythm of her expert deep throat bobbing, she pushed a finger in my asshole.

At first my ass rejected the intrusion. But with a little insistent force, her finger broke through, I gasped, and instantly spewed a load in Joan's velvet mouth.

She kept bobbing, swallowing it all, even as her finger remained lodged partway in my ass, giving me a shockingly intense prostate orgasm.

Once she was done extracting every drop of cum in me, she pulled her finger out, pulled my pantyhose back up and said, "I have one more dirty little fantasy I often fuck myself to."

"What is that?" I asked, as she climbed back into her jeans.

"It's even nastier and more taboo than anything you revealed today," she said, intriguing me.

"I can't fathom that's possible," I said, as she grabbed her t-shirt.

"Oh, it's more taboo than an Asian dude sucking a big black cock," she said bluntly.

"More taboo than having a cross dressing boyfriend you fuck in the ass?" I asked daringly, feeling it so liberating to be able to say such wicked things out loud without any sense of shame or fear of ridicule, instead of being stuck forever with just imagining them in my head, or alone at my computer.

"Yes, and even more taboo than you eating my creampie after my cunt has taken a dozen loads of BBC cum," she said wickedly, now completely dressed, although her panties were still on the floor.

"Oh God, that's the hottest thing I've ever heard," I groaned.

She leaned down and kissed me, and whispered in my ear, her hot breath sending a warm chill up my spine, "My biggest fantasy is a lesbian threesome with me being the submissive slut to my two Mistresses."

"Oh God, that's hot," I moaned, the visual so captivating and erotic but I pointed out, "but it isn't overly taboo."

She walked to the door, stopped, turned her head to me, and revealed, with the wickedest grin ever, "The two girls I want... are my sisters."

I gasped as she walked out of my office and headed down the stairs, right after lobbing me a bombshell just as taboo and twisted as any of the ones I'd unleashed on her, after she'd let herself in with her key to surprise me, and then I'd accidentally turned the tables to surprise the fuck out of her.

"Come back here, you," I called out, imagining her elder sister Denise, a beautiful reddish blonde with amazing curves in a petite frame, and Jeanette, Joan's junior (by only thirteen months), shy academic sister (she was just finishing the thesis for her PhD), in the midst of a sexy daisy chain (of course all three were in nylons in my fantasy... and as it happened, all three ladies were so hot, that I'd already jerked off to that exact same fantasy, and more than once).

"Gotta go. See you tomorrow," she called back, in a tone that said she was getting a real kick out of dropping the bombshell she was now leaving me to deal with.

"If I recover from my heart attack after that reveal," I said, heading downstairs to forestall her.

She was finishing putting on her heels on as she announced, "Tomorrow we go shopping."

"For what?"

"Toys for that cute ass of yours, and a strap-on to strap around these cute hips," she said, posing with her hands on said cute hips.

"Are we really going to do this?" I asked, knowing that Pandora's Box had been not just opened, but nuked to smithereens.

"I refuse to allow my sweet sissy girlfriend to live in denial or regret," she teased, coming over and kissing me tenderly.

"I have no regrets," I said, as I looked into her beautiful blue eyes. "At least not now."

"But if you don't let me help you explore this side of your sexuality, you'll always wonder, and one day you'll regret not following up on today," she prophesied.

"Maybe, maybe not," I said, not yet having any time to process all this... and I was a man who liked to ponder thoroughly, and even make pro and con lists, before making any major decisions.

"There won't be a maybe, and absolutely no maybe not, ever again," she said. "You want to get fucked, and I'm just the girl to fuck you."

"That is the hottest thing you've ever said," I pointed out.

"Hotter than my wanting to be the soft squishy center in a lesbian sandwich with my hot sisters? And if my stern Mistresses allow it, while you watch?"

"Okay," I corrected myself, imagining her rather aggressive older sister taking control of her two younger sisters. "It was the second hottest thing you've ever said."

"And I want to be there cheering you on, when you take that first BBC into your mouth," she added.

"Okay, the third hottest thing I've ever heard you say," I laughed.

"Friday night, after our dinner and the musical, I'm taking your anal cherry," she promised, kissing me one more time, giving my penis a squeeze though my sticky pantyhose, and walked to the door.

"Okay, you make me keep renumbering the order of the hottest things I've ever heard from you," I said, adjusting my penis, which was bent awkwardly in my pantyhose.

"Oh, and beginning tomorrow, your Mistress requires you always to be in pantyhose, or sheer stockings if you prefer, beneath your suit at work, or whatever clothing you're wearing elsewhere," she instructed, opening the door.

"Fifth hottest, or maybe fourth, I'm losing track," I said, completely overwhelmed but in a good way, at the wild turn of events beginning the moment I was caught in the act of watching BBC sissy hypnosis porn and believing my relationship was over... and then miraculously, it wasn't!

She closed the door, leaving me standing there in bewildered awe and soiled pantyhose.

"Wow," I said to myself, as I went back to my office to shut down.

Who would have thought serendipity would play such a wild, crazy, wonderful trick on me?

"Wow, just wow," I repeated to myself as I grabbed her panties off the floor and placed them against my nose. God, she smelt good. I knew these would be resting on the pillow beside me tonight.

I pulled off the pantyhose, took a shower, and got ready for bed. I saw my phone flashing with a picture text from Joan. She was holding a strap-on around her waist (at an adult shop, it appeared) with the message: Sorry, couldn't wait for tomorrow to buy one. Think I'll look hot with this around my waist wearing some lingerie?

I texted back, although her message was fifteen minutes old: First, you always look hot. Second, you'll look amazing when you're wearing that one and it's buried deep in my asshole.

She texted back a few minutes later: I bought a few special items for Friday, and some for the rest of the week.

I texted back, thinking tomorrow was only Tuesday: What did you buy?

She texted back: That's for me to know and you to find out when I want you to.

I texted back: Sigh. Fine.

She texted back: And going forward, NO touching that cock of MINE without permission.

I loved that she called my tiny penis a cock. Thinking of the plethora of stories by silkstockingslover where a submissive is ordered to obey a dominant, I replied: Yes, Mistress.

I got into bed, my tiny penis again hard but now untouchable, as she responded: Good girl.

I felt myself blush at her purposeful decision to call me a girl.

I texted back: Good night, Mistress.

She texted back: Good night, Erica.

My tiny penis flinched, begging for more attention.

I ignored its needs, as I began my journey of utter obedience to my sweet, and apparently dominant (although a switch), girlfriend.

THE END OF CHAPTER 1

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COMING IN A COUPLE OF WEEKS:

Sissification 101: Chapter 2: Where both Eric (a) and Joan discover the joys of toys.