Sissification 101: Ch. 02

Summary: Both Eric(a) and Joan discover the joys of toys.

Thanks to the real Eric who requested and helped plot this lengthy story.

Thanks to Tex Beethoven and Robert for editing this story.

Recap so far:

Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by a very supportive girlfriend.

Sissification 101 Ch 02

3. THE DAY AFTER: MY FIRST BUTT PLUG

TUESDAY

I recalled last night's wild revelations, and after a shower, I went without underwear and wore the pantyhose, as ordered by Joan.

It felt a little weird, but also a little exciting, to have female hosiery on beneath my stereotypical business suit.

The morning was uneventful... I didn't get to see Joan all morning, as I was in meetings. It was a slight rush to be aware that I was wearing hidden pantyhose as we discussed marketing strategy and cash flows, and on the surface, everything was mundane.

I received a text to meet Joan at the Swan Pit for lunch. I immediately knew this was special, since that was the location of our first lunch date... which had led to our first dinner date... which, of course, within two-and-a-half weeks, had led to the official beginning of our committed relationship.

I arrived a few minutes tardy, the meeting going over, even though I'd quit listening near the end, being so excited to be having lunch with Joan... but also feeling a bit nervous. She'd had over a dozen hours to replay last night, and to reconsider her reactions and commitments. I felt pretty confident we'd come together on the same page for this new adventure, yet I wouldn't know for sure until we got together for lunch and I'd be able to tell she wasn't having second thoughts. I mean, it would be very reasonable for her to have second thoughts, but after all, she'd invited me here.

She was already seated, and she'd already ordered for us. She smiled and asked, immediately putting me at ease... no, she wasn't having second thoughts... "So how is wearing pantyhose to work?"

"Liberating," I answered.

"How so?"

"I feel I'm a little more myself," I explained.

"How so?" she asked again, as I felt her foot... no shoe, definitely sheer stocking... appear between my legs and rest itself directly on my crotch.

"Well, I've been hiding a significant part of my identity for years, and although you're the only one who knows my truth now, it's exciting to be secretly living it with you," I answered.

"Oh, we're just beginning to live your truth, and you can bet we'll be living it together," she assured me, adding verisimilitude to her assertion by slowly rubbing my cock.

"So, no second thoughts?" I asked, even though it was obvious she didn't have any... yet I still needed to hear it said.

"Oh, I've had second, third, fourth, and hundreds of thoughts."

"Oh," I said, that not being the answer I'd been hoping for.

"But most of them were about tactics for making all our fantasies come true," she revealed, my sudden anxiety relieved just as quickly as it had arrived... especially how she'd referred to them as 'our' fantasies.

"Oh, better," I smiled.

"Were you worried I'd cut and run?"

"A little," I admitted.

"If I was going to run, I had lots of opportunities last night," she pointed out, "one of the later ones being on my way to the adult store to select some toys for us."

"I guess so," I chuckled awkwardly.

"Catching you with that sissy video, for instance," she said. "You were afraid, as the expression goes, I'd be 'shocked and appalled'."

"Yeah," I nodded, shame again coursing through me.

"Then there was your plethora of admissions," she continued. "You were scared shitless I'd find one or all of them to be a deal breaker."

"Yeah," I sighed to myself, thinking almost no one used the word 'plethora'.

"And all those declarations," she added.

"You told me to say them," I protested.

"But hadn't you made those same declarations while you watched them alone?" she asked. "Many times, beginning sometime before we met, and then even continuing after we met and got together, keeping your dirty little secrets from me? Some women would be very upset about that."

"Yes, you're right," I admitted.

"But I'm not some women, I wasn't even mildly upset by any of it, and I'm still here," she said.

"Yes, you are, and I'm so very grateful that you are," I said, filled with gratitude.

"This is going to sound corny, but I want to be a part of your journey," she said. She then paused and added, "I want to make it our journey."

"You do?" I asked, even though it was obvious from her reactions last night, and now her words today, that she meant it.

"Yes, Eric," she said softly. "I want to do everything with you."

"That's music to my ears, because I want to do everything with you, too," I said.

"Good, then we'll be together every step of the way," she concluded, as the waitress arrived with our food.

"I couldn't be happier," I said, a rush of joy coursing through me.

"Although you must understand..." she began and then paused, her tone suddenly ominous.

Oh dear, here it is... a variation on 'I like you, but'.

"...that I'm the one in charge," she finished after an excruciating delay.

"Haven't you always been?" I joked.

"Well, yes," she smiled. "But now it's official."

"Should we put it in writing?" I joked.

"No," she laughed, "but we shall consummate our hierarchy on Friday."

"We shall, shall we?" I smiled, as she continued rubbing my hard penis.

"Oh, you know we shall," she said in a way that made it clear she'd already planned the night... well, the end of the night... I'd planned dinner and a musical, and those were still in our itinerary.

"I'm both excited and terrified," I only kind of joked.

"Given what I'm planning, each of those emotions are logical and appropriate to have," she smiled, as she moved her foot away.

"Hey, I was enjoying that," I protested.

"First, you're not allowed to come until Friday night," she said, that being a mighty long time for me, as I tended to jerk off every night, even nights when I'd already come in Joan's mouth or pussy.

"Okay," I agreed tentatively.

"What? That's only three days," she said.

"Four days and three nights," I corrected her.

"Fine," she sighed, "but my requirement stands," shaking her head and taking a bite of her food.

"That was the first point. Is there a second?" I asked, both scared and curious as to what it might be.

"Right," she said, her response surprising sarcastic, "Sorry, I got distracted by the 'unbearable hardship' I'm putting you through," using air quotes.

"Yeah, yeah," I said, hating not knowing something.

"Second," she said as she sliced her chicken, "there shall be no foreplay during breakfast, lunch or dinner. Our interrelations shall be strictly platonic... until they're not."

I laughed, leave it to her to make a rule about food. We really were two peas in a pod. "Great rule," I agreed, finally realizing I hadn't taken a bite so far, I was starving, and when I looked down at my plate, I saw the dear woman had ordered me the exact same meal I'd ordered myself on our first lunch date.

We ate in relative silence, talking only about boring things like work, that seemed excessively mundane compared to last night and the promise of Friday... that evening seemingly an eternity away right now.

Once we were done eating, she asked, "Do you want dessert?"

I asked, wanting clarity, stressing the last word, "Dessert, dessert or an actual dessert?"

"Unless you're about to crawl under the table to get the dessert you're angling for, I was just thinking dessert, dessert," she said.

"Although that sounds fun, and something to add to my suddenly expanding bucket list, I'll just stick to dessert, dessert as well."

She shook her head, "I just want whatever cheesecake I can extract from this weird game of innuendos you've created."

"Excellent choice, ma'am," I said.

A shared cheesecake later, she said, "Don't leave work today without dropping by my office. I have a gift for you."

"Why does that scare me?" I asked, kinda playfully.

"It shouldn't," she said, then added as she stood up, "much."

"You both turn me on uncontrollably, and frighten the dickens out of me at the same time," I said, also standing up.

She kissed me and said only, "Good," before we walked back to work together.

The afternoon was super busy, and I actually forgot I was wearing pantyhose until I went to the washroom to pee. I unzipped, and was reminded I was in pantyhose. No one else was in the bathroom, so I performed some weird origami maneuvers with my pantyhose, pissed, settled my hosiery back in place, and returned to work.

The workday ended, and I went to Joan's office. I walked through the door and closed it.

"Lock it," she ordered.

"Already in Mistress mode, I see," I joked, as I dutifully locked the door.

She stood up, approached me around her desk, then raised her dress to reveal she was wearing a strap-on.

"Oh my," I gasped. "You're really in Mistress mode."

"Like?" she asked brightly, as she stroked her very black cock.

"It's very unexpected," I said, as I stared at it nervously.

"Don't worry, I'm not going to fuck your ass in my office," she said. "I just wanted to give you a little peek at what I'll be wearing on Friday when I take your cherry."

"It's not as big as the one you had last night," I said, beside myself with excitement that she was wearing a strap-on, but equally full of trepidation.

"Yes, the saleswoman suggested that if I'm breaking in a virgin ass, and yes, she used the words 'breaking in', I should begin smaller," she revealed.

"Did you tell the saleswoman it was for a guy?" I asked.

"I did," she nodded.

"Oh," I said. This suddenly all seeming so real. Yes, I was excited about exploring these sexual curiosities and doing it with Joan, but I didn't want anyone else knowing.

"Come suck my dick, Erica," she ordered, not noticing my sudden nervousness. Whether from lack of observation or by design, I couldn't say.

"Right here?" I asked, trying to hint at my trepidation, even though her words were so fucking hot... words that for weeks I'd secretly imagined her saying to me.

"Just for a minute," she said. "I've been so fucking horny all day, imagining you sucking dick."

"Really?" I asked, surprised that the idea got her excited, but still concerned, because we were in her office, and the corridor outside was far from empty.

"Yeah, I can't explain it," she said, "but the idea is a major fucking turn-on."

"It is?" I asked, still in awe that my dirty fantasies could turn a woman on.

"Stop acting so shocked," she said. "I've always been a bit of a sexual deviant, and it seems that so are you."

"I never thought of it that way," I said, her words relaxing me a little.

"It's a good thing," she said. "We can explore these kinky fantasies together."

"Okay," I said, relaxing a little bit.

"Now get over here Erica, and suck my fucking dick," she ordered, just one more sentence to add to the growing list of super hot things I'd heard uttered from her lips.

"You had me at 'suck my fucking dick'," I joked, having watched Notting Hill with her just last weekend. She loved English movies, and I was just now discovering English movies... especially Love Actually and Almost Time... behind all my kinky fantasies, I was also a romantic at heart.

I walked over to her, dropped to my knees, and hesitated.

It was one thing to fantasize about doing this.

It was another to have it staring me in the face.

My hand was trembling as I reached for the plastic cock. I stroked it, leaned forward and kissed it.

Even after all my hours of watching dicks getting sucked (I couldn't even begin to imagine how many hundreds or even thousands of hours that would total), I realized I had no clue what I was doing.

I licked the shaft, a little surprised I could smell her scent as I did. This was turning her on and stimulating her pussy. That, in turn, excited me.

I licked up and down for thirty seconds give or take, feeling so many conflicting feelings as I did. I liked being on my knees. I liked having a cock in my hand (although it made me wonder what a real cock would feel like). I liked having Joan watching me; she was my safe person, even though she scared the wits out of me sometimes. Yet I also felt a little 'less'. I felt like less of a man, which I'd pretty much accepted in my many fantasies at home, yet it felt way more real when my girlfriend, kindred spirit that she was, was standing above me.

These many thoughts were spinning in my head and through my body, my tiny dick hard as ever, until Joan ordered, "Enough foreplay. Suck my cock."

"Yes, Mistress," I said, liking her nasty words, enjoying being told what to do. I opened my mouth, still trembling ever so slightly, and took the six-inch slim cock in my mouth... so much smaller than the big black cocks I constantly fantasized about sucking.

"So hot," she purred, as I began bobbing.

Truth be told, it was a little awkward.

Partly because I was in her office and could still vaguely hear people right outside, and I couldn't help but wonder what they'd think if they knew what was happening behind the door.

Partly because it wasn't a real dick.

It was nevertheless super stimulating.

My hard penis flinched in my pantyhose from sucking a plastic dick.

"You're going to be a great little cock sucker," she said, sounding turned on, watching me.

I kept bobbing, suddenly wanting to impress her. I was a great pussy licker, I knew that; now I wanted to become a great cock sucker.

Cock sucker.

What a word.

Seldom used, except in a derogatory way.

You never called a girl who sucked a dick a cock sucker. No. Sometimes a slut, if she sucked a lot of different dicks and you thought you could get away with it, but a girl sucking a cock was just a girl sucking a cock. On the other hand, a guy sucking a cock was a cock sucker... or a faggot... or gay. Or some other name most men didn't want to be labeled as, and therefore usually derogatory.

I suppose the same principle could be used to describe pussy licking. A guy eating a pussy is just a thoughtful, considerate guy doing what he should... but a girl eating pussy is a lesbian, or a dyke... although the principle breaks down at the next step: there's no derogatory term synonymous with cunt licker or pussy muncher... those are hot terms when applied to a woman.

I continued bobbing, realizing I was only taking about four inches in my mouth before feeling filled up. How could I possibly take ten? How did anyone take ten?

"That's enough for today, my sexy cock sucker," Joan said, her tone making her words sound so sweet, as if she was saying something sensitive like 'you look hot today.'

"That was wild," I said as I backed off the cock.

"I think we're going to have to work on your gag reflex," she said.

"Looks like, how does anyone take a big cock in their mouth?" I asked.

"Practice," she smiled, as she stood up and slid her cock back in my mouth.

To my surprise, she then briefly fucked my mouth, shoving all six inches in, and making me gag big time.

Like many black men I'd seen online do to their hungry sluts, she grabbed both sides of my skull, taking full control of me as she fucked my mouth.

This rough treatment made my penis flinch, and had a chill going up my spine. Despite my severe discomfort, seeing that Joan was obviously getting into it, enhanced my own pleasure. It seemed the strap-on was creating some sort of friction on her clit, as she moaned rather loudly while she skull-fucked me, albeit with a dick almost as small as mine.

It was quite awkward; my entire sex life I'd been in control, or had at least a semblance of control, and suddenly I had none. Even while sucking her cock, I'd been in control even though I was clumsy at it, but while she was face fucking me, I had none.

And as I said, the entire time I was gagging, the most worrisome part of that being those loud noises you make when you gag, with other people still in the building.

She pulled out and added, looking down at me, my saliva drooling in torrents down my chin and dripping off her cock, "Apparently, lots and lots of practice."

I wiped the saliva off my face as she surprised me yet again by ordering, "Undo your pants, pull them down, and bend over my desk."

"What?" I said, having heard her, but thinking she'd already said she wouldn't fuck me here.

"I picked up a little something for that virgin hole of yours," she said, as she walked back around her desk and picked up a small butt plug.

"Oh," I said, relaxing slightly as I unbuckled my belt... getting a little excited.

"Yes, three days, three plugs," she said.

"Oh," I repeated, as I pulled my pants down.

She walked back behind me and said, as I bent over only in pantyhose again, "God, you have such a sexy, fuckable ass."

"Words I never imagined being said about me," I joked awkwardly.

She caressed my pantyhose-clad ass and said, "Me neither, but here we are."

"Here we are indeed," I agreed.

"Oh, shoot," she said, returning to her desk. "I almost forgot the lube."

"That would be utterly lube-icrous," I joked.

"Nice," she smiled, grabbing the lube, and as usual, appreciating my corny sense of humour. "I bought a big bottle for each of our homes, plus a small one for my purse."

"Always thinking ahead," I smiled, as she returned behind me.

"That's me," she said, again caressing my ass. "Fuck, I think you've got a sexier ass than I do. Where's the fairness in that?"

"No, I don't think so," I said, even though I appreciated the compliment.

"No really, it's actually quite feminine," she said, as she really checked out my ass.

"I don't know how to take that," I joked.

"Well, Eric would be within his rights to be slightly insulted and insecure about his girlfriend seeing his body as feminine, while Erica should be super flattered that her hot curves can compete with her girlfriend's," Joan said.

"Oh," was all I said as she pulled my pantyhose down to my ankles.

"You'll always be Eric at work, but in the confines of the bedroom and," she paused, "when we're in my office with the door closed and locked, you'll be Erica. Is that clear?"

"Yes, Mistress," I agreed, wondering if it could be that simple to split my persona like that, as I felt slightly warm lube being poured between my ass cheeks.

"Good girl," she said as she probed my anal entrance with her finger. "We're in this journey together though, so if there's something you're not comfortable with, please tell me."

"Like being fingered in your office?" I groaned, as her finger slid inside.

"For example..." she said as she pulled out her finger and then a moment later, pushed the smallest of the butt plugs into my ass. "...this!"

I moaned, although after a brief period of stinging, there was nothing.

"The first plug is small," she said, as she pulled my pantyhose up.

"Yeah, I can barely feel it," I admitted.

"Nevertheless, it has its job to do, so keep it in your ass all night and all day tomorrow, until we swap the plugs after work," she said, then quipping, "Your gracious Mistress will allow you to remove this whenever you need to poop; fair's fair." She then slapped my ass. Hard.

I yelped, surprised by the sharp pain.

"Fuck, your ass is hot," she said.

"Thanks," I said, really liking her obsession with my ass, even though it burned for a bit after the sudden slap.