Summary: Competing sisters use their sissies for dominance.

Thanks to Eric who requested and helped plot this lengthy 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 as Eric begins his sissy training by getting his ass trained for cock and his tiny clitty caged by his girlfriend as the hierarchy is established with Joan in control.

Sissification 101 Ch 03 as Eric is pegged for the first time by his girlfriend.

Sissification 101 Ch 04 as Joan rents a hotel room for their first black cock for both of them. Eric(a) sucks his first BBC, gets spit-roasted by Joan's strap-on and takes a facial; Joan then reaches multiple orgasms from Carter's BBC; the scene ends with Eric(a) tasting his first BBC creampie.

Sissification 101 CH 05 as Eric practices his cock sucking on toys and Carter while Joan is gone for the week. Joan returns and they go together to a gloryhole and enjoy a few black cocks.

Sissification 101 CH 06 as Eric takes his first cock in her pussy and is spit-roasted by two BBC's; Joan meanwhile tastes first BBBW pussy.


The next few weeks continued as a whirlwind of sex. Sucking cock, getting fucked, getting pegged, bukkakes... and that was just my part of the action.

Joan also got her fair share of black cock, plus she really enjoyed pegging me.

We also, obeying Carter's order, got spade tattoos. Mine was inked right above my ass on my right side, while Joan's was right above her shaved pussy. So each of us now had a permanent reminder of which race of people now owned our fuck holes.

I'd moved in with Joan, we'd gotten engaged, and then just when I thought I couldn't possibly experience any more surprises... I was given perhaps the most life-changing one yet.

Joan said, as she drove us to my surprise, the first of many she had promised me for the day, "So today you're to do whatever I say, without question or hesitation."

"Don't I always do that?" I asked, since my caged clitty, my spade tattoo, the constant plug in my cunt and the pantyhose I always wore, were all evidence of my complete obedience to her in sexual matters.

"True, true," she smiled, "but today we're stepping it up a notch."

"I can't fathom how that's even possible anymore," I said, both excited and frightened by her words. Excited, because every time she'd surprised me since she'd accidentally outed me to herself had resulted in yet another fantasy coming true and provided pleasure beyond what I'd ever imagined. Frightened, because I seriously couldn't think of anything we could possibly do that would be 'stepping it up a notch' without it being a blood sport, or something else really out there and in the realms of being harmful. I mean I'd already been going to the college bathroom weekly, where I was spit roasted by at least a dozen cocks a night; I'd taken over twenty loads in my first bukkake, and even taken eight loads in succession up my ass. I'd worn cum all over my face while we strolled through an indoor mall south of the city in broad daylight. I'd been ass fucked in the parking lot of a bar while strangers had watched, I'd sucked off three complete strangers in an adult movie theatre... what else could possibly be left to do?

"Oh, just you wait," she said, in a tone that was both mysterious and sexy, and which conveyed the hint of a promise that I would soon find myself in shock and awe... which were the perfect descriptors for many events in our relationship, ever since she'd caught me wearing pantyhose and interacting with sissy hypnosis videos.

"Now you really have me curious," I said, as she drove us into a part of the city I seldom went to... where most of the clubs were, and a lot of the Fetish shops.

"Bi-curious," she teased.

"Between you and Carter, and our other new friends, I'm way past that," I laughed at her lame attempt at humour.

A couple minutes later, we were parking outside a sex shop I'd never been to. I asked, "Does this shop carry products our regular store doesn't?"

"In fact it does, in a way," she answered. "It caters to a very special clientele."

"Special clientele?" I asked.

"Let's just go inside," she said, enjoying the effect on me of stretching out the mystery for as long as possible.

"Your look and tone are scaring me a little," I confessed as I got out of the car.

"That's deliberate, my dear sissy. But you know that I always have your best interests at heart," Joan reassured me unreassuringly, as she took my hand and led me forward. I noticed a prominent sign on the door announcing Admittance by Appointment only. Call 555-6644 to Request Arrangements

"True, true," I nodded, having complete faith in Joan... who truly had never steered me wrong; instead, she had consistently steered me straight into various versions of heaven.

"Plus, I have a whopper of a surprise for you tonight," she added.

"Ten-inch black cock?" I asked, having sucked and been fucked by BBC almost every day since taking on those first perfect BBC's.

"Better," Joan said, squeezing my hand.

Two ten-inch black cocks?"

"Even better," she said, before adding after a pause, "well, that is if you win."

"Win what?" I asked, her really drawing me in.

"You'll see," she said enigmatically as we walked in, and to my surprise I discovered we'd just entered not a store stocked with sex toys, videos and the like, but an interior that looked exactly like a salon.

In the salon, which was fully functionally just that, I was given a mani pedi, and then was sent to a back room, where I met with a beautician to get my eyebrows shaped and my make-up done (pink eyeshadow, blush and lipstick).

The woman then ordered me to get naked... "No little lady, I'm not joking; those are your Mistress Joan's specific orders," and then she gave me a full Brazilian -- my first one ever. Which meant... humiliatingly... that my caged clitty was the centre of her attention for several painful minutes, with my butt plug also onsite for her ministrations. Being a professional, she was apparently unfazed by any of it, but still.

I was then led into another room, still naked, my clitty burning with lust and humiliation, as girl after girl turned me into one of them... each of them very amused to be doing so. Then I was completely dressed by a girl who looked to be no older than eighteen: she adorned me in pink stockings... fishnets no less, a pink crotchless thong which framed rather than covered my cage, a padded pink bra that made it look like I had decent-sized breasts, a tight, bright pink short club-hopping dress (imagine Legally Blonde pink), six-inch matching stripper heels, and a blonde wig styled in a bob with pink streaks. And of course my butt plug remained in place, which was ubiquitous these days. There were no mirrors in the room, so I had no idea what I looked like... and damn, was I curious. This entire makeover was a little humiliating, and yet ultimately exhilarating, as Joan was obviously orchestrating the next step on my journey to full sissification.

Joan finally entered the room after I'd been left alone for a couple minutes, and she said, "Holy shit!"

"What's wrong?"

"Nothing at all. You look so fucking hot!"

"I do?"

"If not for your Adam's apple, there wouldn't be a clue showing that you used to be a man!"

The phrase 'used to be a man' should have been hurtful... I was still a man, in the anatomical sense at least... yet her flattery... for that's how I saw her kind words... only enhanced my excitement. Every step of the journey to my feminization had been a new high, and I'd even begun wondering what it would be like to perhaps transition completely into a female... although I had yet to mention the idea to Joan... not sure how she would take it, and not sure how that would work in the real world of business associates, clients and family. My parents would be shocked even to know I sucked BBC, or that I got fucked by BBC and dressed in feminine clothing. "I'd love to see myself," I pleaded, dying to see what I looked like after about three hours of feminization.

"Soon," she promised, as she pulled something from her purse. "But first, I got you a gift."

"You didn't have to, Joan," I said. "This whole day so far has been a wonderful gift."

"I never have to," she agreed, handing me a jewelry box. "But like always, I wanted to."

"Thank you," I said, excited to be given jewelry... shit, I really was becoming a girl.

"I think you'll love it," she said.

"I'm sure I will," I said, as I opened the box. And then, "Oh my."

"Those aren't real diamonds," she said, as I examined my new pink collar with the prominent words 'sissy slut' spelled out in clusters of fake diamonds.

"You can't even buy your best girl real diamonds," I faux complained.

She smiled, "Maybe for an anniversary."

"I love you so much, Joan."

"I love you too, Erica," she replied with a touching smile.

"Oh... and one final thing to complete your ensemble," she said.

"You spoil me so much."

"I really do," she agreed, as she handed me a pink purse.

"I definitely needed that today," I said.

"I put everything in your wallet into a prettier pink one," she added.

"Thank you," I said, feeling so girly... oddly feeling like the person I'd always wanted to be.

"Now, let's go," she said.


"To give your new look a test drive."


"Let's see if you can pass for a woman in public."

"Fun!" I squealed in my best falsetto, both excited and nervous about the prospect. "But first, can I pleeease see what I look like?"

"Oh, shit, yes of course," she nodded, taking my hand and leading me into another room to face a large mirror.

"Holy shit," I gasped.

"I know."

"I don't look remotely like myself," I said, staring at a hot-looking woman staring back at me.

"You make a fucking hot woman," she said.

"I really do," I said, admiring my new look, which was utterly slutty and feminine.

"Let's go," she said, leading me out of the exclusive salon hiding behind the sex shop fa├žade, and into the adjacent mall saying, "Go buy the new Taylor Shift vinyl, and don't be in any hurry."

"Really?" I asked.

"Yep," she nodded. "And remember, no questioning or hesitating today."

"Okay," I agreed, always doing whatever Joan told me to. I left her behind and walked... or rather sauntered through the mall, the record shop being at the opposite end of it, receiving dozens of looks. Most of them portrayed shock rather than admiration, and I couldn't tell whether it was because they could tell I was a crossdressing man, or because I looked like a hot girl who was dressed like a complete skank.

Most men... at least the ones who valued their testosterone, would be mortified to be dressed as I was and attracting the looks I was receiving, yet for me it was the ultimate rush! Seeing women looking at me in disgust and men checking me out and needing to adjust themselves, was so fucking exciting!

I reached the record shop and wandered around, fielding more looks, both judgemental and leering ones. I finally found the vinyl I was looking for, walked up to the till and handed the nerdy-looking guy the album. He asked, "Is there anything else, ma'am?"

"That's it," I replied, trying to reply in the feminine voice I'd been practicing for a few weeks.

"That will be $17.89," he said, unable to avoid looking at my chest.

I pulled my brand new pink wallet out of my brand new pink purse and handed him a twenty, so excited that he thought I was girl and was checking me out.

He handed me my change, and I said, "Thanks, sexy."

"You're welcome, ma'am," he said, his cheeks going bright red.

"Thanks especially for checking out my tits," I said wickedly. "It's always nice to know I've still got it." I then turned and swayed my ass away, feeling the ultimate rush.

I walked out of the shop and headed back towards the car, although I wasn't sure where we were supposed to meet. Suddenly my purse was ringing... playing Barbie Girl. Apparently Joan had also changed my ring tone.

I pulled out my phone, which also had a new pink phone case, and said, seeing it was indeed Joan on the line, "Yes, Mistress."

"Meet me at the pet store."

"I'll be right there." We'd been discussing getting a puppy for a couple of weeks.

I reached the store, after searching it out on the map pedestal, and saw Joan chatting with a pretty college-looking girl.

"There she is," Joan said as I approached. "I need a leash for her collar."

"Oh," the girl said, very surprised.

"Do you have one?"

"I'm sure we do," she said, giving me a look that could only be described as perplexed.

We followed her through the store, receiving a few odd looks from other customers, until we arrived in a section displaying quite a few dog leashes.

Joan grabbed one, hooked it up to my 'sissy slut' collar and ordered, "Kneel."

I obeyed, true humiliation no longer something I felt... even as I took in the stunned look on the girl's face.

"Crawl," Joan ordered.

It was challenging in my tight dress, and the lacy tops of my nylons were on display, but I obeyed until Joan said, "Perfect. You may get back up."

"Thank you, Mistress," I said, getting up.

"Is that a guy?" the college girl asked, completely bewildered.

"On her driver's license, yes," Joan said; but added, "otherwise she's a complete woman."

"Wow," the girl said.

"Yeah, she's still in the process, but she already looks pretty feminine, doesn't she?" Joan asked, as she unfastened the leash from me.

"If it wasn't for the telltale words on her sissy collar, I'd have had no clue," the girl said, politely cooperating with my alleged new gender.

"Perfect," Joan said. "You passed, Erica."

"Thank you, Mistress," I replied, enjoying the reactions from this pretty girl.

"Every girl should have their own pet," Joan told the girl.

"Maybe. I've never thought of it," she said before asking, clearly a little uncomfortable, "May I assist you with anything else?"

"No, this is what I need for her special training tonight," Joan said. "Thank you very much for your kind assistance."

"You're welcome," the girl said, and then left.

"I think we may have scarred her for life," Joan laughed, as we walked towards the till to pay for the leash.

"Or opened up a whole new world to her," I suggested.

"Perhaps," she smiled, handing me the collar. "Go pay for it."

"Yes, Mistress," I said, going to stand in line.

As I did, I heard a woman say, "Look at her."

I turned, assuming she was talking about me, although not at all kindly, so I waved and blew her a kiss.

Dismayed, the older woman shook her head and scuttled away.

I paid for the leash as the male salesperson looked at me, perplexed.

Once the transaction was done, I told him placidly, "In case you were wondering, I have tits and a penis," before turning and walking away.

Joan said, as we walked to the car, "I think you're well on your way to becoming a true woman."

"I'm really enjoying this," I admitted.

"I knew you would," she smiled.

"I mean, I can even imagine living my entire life as a woman," I said, giving her my first hint of my idea of transitioning.

"Are you saying what I think you're saying?"

"Maybe, "I said sheepishly, before adding, "Or maybe not. I'm not even sure whether I'm saying what I'm saying."

"Are you thinking like hormones?" she asked.

"I don't know," I admitted. Then after a pause, "Well, yes. Sometimes."

"Like losing your cock and getting a cunt transition?" she asked. "Or keeping your clitty, and just getting a real pair of titties?"

I laughed at the way that rhymed before I said, "I honestly don't know, but I definitely like being like I am today."

"I like the idea of your being a chick with a dick," she opined. "I'm less fond of the idea of losing your clitty and getting yourself a pussy."

"Yeah, I don't really want a pussy, I've already got one," I said, referring to my asshole.

"But a nice pair of real tits to play with, would be hot," she nodded, looking me over.

"I'm not sure I could go through even with that," I admitted, "but I agree the idea is hot."

"Yes, it is," she nodded, as we reached the car.

"But that would be hard either to explain or to conceal at work, or to my family," I pointed out the obvious problems with it... besides the need for taking hormones and all that.

"Yeah, I think we'd have to do a lot of research and soul searching, if you seriously thought you might want to do that," she said. "And you'd have to be sure beforehand, since it's pretty much a one-way street."

"It is just a thought, at least for now," I said.

She smiled, "Understood. But remember, there are no secrets between us ever again, and that goes both ways. So if you ever start thinking about it seriously..."

"I agree," I said, relieved she hadn't freaked out, yet also happy to get an idea of what she'd be able to accept happily, and what she wouldn't.

In the car she said, "Lets put a pin in that conversation for now. I have a very big surprise waiting for you." She'd stressed the word as she began to drive.

I said, "You have me so curious," stressing a word of my own.

"It's about to become an epic night," she said.

"We've already had a number of those," I smiled.

"Yet this one may be the most epic one yet, and with lasting consequences," she said, giving my leg a squeeze.

"My fishnets are a lot skankier than the nylons, and less sexy," I said.

"Yes, but you're wearing the outfit she chose for you, not I," she said.

"She?" I asked, that pronoun coming as a surprise. Sure, we'd played with a couple of black women, but the nights we considered 'epic' had always been presided over by a man... a black man, of course.

"Not only is she a woman, but she's also white," Joan added, compounding the intrigue, which was beginning to feel like a mystery for me to solve... lately we'd been watching those lame and predictable, yet somehow addicting, Hallmark murder mysteries.

"I feel like Aurora trying to solve this week's mystery," I said.

"Imagine Aurora Teagarden stripping naked to investigate some sex mysteries where nobody dies and everyone gets off," Joan smiled, both of us having agreed that both the actress and the character would be awesome to fuck, since she was cute, sexy and often wearing nylons.

"I'd love for her to be here right now, helping me to solve this confusing mystery," I said, as she continued driving.

"Oh, it will all come to light soon," she said.

"And like in the televised mysteries, is this mystery woman someone I've known all along?"

"She is," Joan nodded, adding another intriguing layer to this mystery.

"Now you have me completely intrigued and mystified," I said, as she pulled into a hotel's parking lot. "And the mystery unfolds," I smiled, even though which hotel this was gave me no more evidence towards deducing who his mystery woman was... still being stuck on her being white and someone I knew... and someone Joan also must know, since she'd arranged this with whoever it was. But was I aware that Joan knew her? I still wasn't getting anywhere. Except that this mystery woman was the one who'd chosen my getup, so tonight she'd probably be serving as my Mistress. Or rather I'd be serving her. Which should have scared me, yet my undying loyalty to, and my trust of Joan, left me with no fears.

Pub: Dec 22 2020 12:53 UTC
Views: 59