Sissification 101: Ch. 04

Sissification 101 Ch 04

Summary: Eric sucks his first BBC in a threesome with Joan.

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 his 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 their hierarchy is established with Joan in control.

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

Thanks to Tex Beethoven and Robert for editing this series.

7. THEIR FIRST BBC

Saturday

Following our momentous and ground-breaking Friday evening, I woke up, and Joan was lying beside me.

God, she was beautiful.

Radiant.

It was still a little hard to believe she'd not only supported me in my very offbeat sexual exploration from almost the very moment she'd learned about it, but was also playing such a pivotal role.

I went downstairs, made her some breakfast, and brought it up to her.

She was just waking up when I entered the bedroom. I smiled and said, "You slept in. All that fucking must have worn you out."

She smiled, as I walked to the bed with the tray, "Yes, it did; but I also learned something last night."

"That your boyfriend is a sissy slut?" I asked.

"l already knew that, silly," she said, as she took the tray. "No, I didn't realize how much work doing the fucking is. I burnt a ton of calories, and actually broke quite the sweat."

"Well, anytime you want to use my cunt for your cardio workout, just let me know," I smiled, although meaning every word.

The first time you get a blow job, all you want is more blow jobs.

The first time you get laid, all you want is to get laid some more.

So not surprisingly, after the first time you've gotten ass fucked and discover the unbelievable feeling of having a cock buried deep in your back door, all you want is more dick back in your ass... or in my particular kink... in my cunt.

"I may be taking you up on that offer regularly," she smiled, before adding, "but for now, I'm going to enjoy this thoughtful breakfast you made me, while you enjoy the breakfast I've been keeping warm for you all night."

"Mmmmmmm, my favourite meal," I said, wondering if cock cum would one day replace her cream as my favourite snack. But then I realised that cock cum already creampied into my girlfriend's cunt would be the pinnacle of both culinary options.

As I crawled under the sheets and between her (still in black stockings), legs, which I'd barely had time to enjoy in last night's wild escapades, she added, again somehow able to read my mind, "Pretty soon you'll be a cum connoisseur; a sommelier of the sweet homemade gift from both genders."

"I can't wait," I said sincerely, as I moved my hands up both her nylon-clad legs, wondering if that was what today's surprise was to be.

"Now take your time down there," she ordered. "I want to enjoy my meal."

"Yes, Mistress, I want to enjoy my meal too," I replied, as I extended my tongue and leisurely grazed on her sweet pussy.

For twenty minutes, my neck actually getting a little sore, I slowly licked her, exploring every inch of her pussy over and over again, until she grabbed my head and shoved it roughly into her pussy. I took the wordless cue, and attacked her clit with reckless hunger.

A couple minutes later, she came on my face.

She let go of me, I lapped up the rest of her juices, and crawled back out from under the covers.

She asked, "Ready to continue your training today?"

"Yes," I nodded.

"Good; I have something fun planned for tonight."

"What is it?"

"You keep asking questions I have no intention of answering."

"You can't blame me for trying," I smiled.

"I most certainly can; what is it about enjoying delightful surprises you don't get?" she sighed, stretching, "God, I'm a little sore from last night's workout."

"Are you in the mood for some morning cardio?" I asked, hoping for another back end pounding.

"I'd love to," she said as she glanced at the clock, "but I'm meeting my sisters for lunch."

"Lunch?" I asked, trying to sound flirtatious, recalling her fantasy of having an incestuous lesbian threesome with her two sisters, "lunch, lunch, box lunch!"

"That's right. If the opportunity presents itself, I'll eat both my sisters' cunts right under the table," she said wickedly.

"Oh, God," I groaned, the image of my hot girlfriend kneeling under a table licking her sisters' pussies was one of the most amazing, clitty tingling images ever.

"Yeah, I bet they both have tasty twats," she continued.

"I can imagine," I said, imagining just that.

"Don't you dare imagine my sisters' cunts," she scolded playfully as she got out of bed. "Your tongue is mine!"

"I was just imagining you on your knees between their legs," I defended.

"So was I," she winked, giving me a peck and heading to the shower.

"Fuck, my poor clitty," I said as she left me alone.

She returned a minute later and said, "I have an idea for tonight's rendezvous."

"What?"

"Let's do your nails."

"Really?" I asked, even though I liked the idea. I'd considered doing my toenails more than once, but never had.

"Yes, and I even got you a special colour to go with your outfit," she said.

"Ruby red?" I asked.

"Close," she said, tossing me the bottle.

"White?" I asked, this colour seeming so wrong against my brownish Asian skin.

"Yep," she said, "you still have a lot of virginities to be taken."

"That's the weirdest sentence ever," I joked.

She shrugged as she unclamped my white stockings, "You deny having virginities? There are cock sucking, spit-roasting, a real BBC in your pussy, being cuckolded, a BBC bukkake (which I might join you for), just to name a few."

"Oh, God," I groaned, her nasty list making my caged clitty ache.

"It's the truth," she said.

I got out of my stockings and watched in awe as she painted my toenails white. She then said, as she moved to my fingers, "These you can remove before work on Monday, but the toes remain painted."

"Yes, Mistress," I agreed, knowing I would always obey her, and happy she understood that work was work, and play was play.

"So cute," she said, once she was done.

"I never thought cute would be used as an adjective to describe me," I said, even though I was flattered by the compliment.

"And yet you're completely cute," she said, kissing me and then adding, "the cutest cutie cunt licking, cock taking, cute little sissy ever."

"You just always know the right words to say," I smiled, as she cupped my caged clitty.

She knelt down and talked to it. "And you, my sweet little clitty, are the cutest caged clitty in the world."

"Such poetic alliteration," I smiled, as she blew hot breath on my clitty, making my entire body shiver.

She stood back up, shrugged, and quoted, "I'm a poet and I didn't even know it."

"Stick to your day job," I joked.

"What about my night job?" She asked.

"Night job?"

"Mistress," she said.

"Yes, you should definitely keep that job, too," I said as she kissed me again and went to the bathroom.

She showered... called an uber... and left... saying she'd go home to change and fetch her car, and would be picking me up at 6... but she wouldn't tell me where we were going.

I showered... read the newspaper... did some online work... just trying to get through the day. The trivial aspects of day-to-day life now seemed completely irrelevant and mundane since being caught in the act.

I made supper.

I texted Joan: What should I wear tonight?

She texted back: The same white lingerie as yesterday. We have another christening of sorts... more of a baptism.

I texted back: That sounds cryptically hot.

She responded: Oh, it will be. See you soon.

I texted back: I can't wait.

I got back into yesterday's lingerie... and realized I still had no idea where we were going.

I texted: What is the dress code for tonight's date? I mean on the outside.

She responded a minute later: Casual.

I grabbed a pair of jeans and wore a new bamboo baby blue t-shirt I'd picked up recently. Joan, much to my shock, arrived five minutes early... which may have been a first ever.

Joan, being the man in our relationship, just honked and didn't even get out of her car. I submissively went outside and got in the car.

She was in a cute dress that had almost the same coloured baby blue top. "We match."

"Great minds think alike," I laughed. "Although I feel a little underdressed compared to your outfit. Where are we going?"

"Someplace special," she answered. Then after a pause, "For dessert."

"Chocolate?"

"I believe chocolate is de rigueur for us these days," she smiled as she kept driving.

"Yummy," I said, my tiny clitty tingling with anticipation from her vague answers. I mean if we were going out for something as everyday as pizza, she'd tell me. And I probably wouldn't be wearing a white negligee with my nails polished.

"Yummy, indeed," she smiled.

We pulled into a hotel parking lot. This was her surprise? How sweet. Would Carter be here too? Or was this a romantic, although likely kinky, rendezvous?

"This is the surprise?"

"It is," she nodded. "Just an intimate night... in the honeymoon suite."

"Oh, nice," I said, thinking this was incredibly sweet, and yet feeling a little twinge of disappointment I wouldn't be sucking Carter... something I'd had a hunch was in the cards for tonight.

"Yeah, a night of romantic decadence," she smiled as she parked.

We strolled inside hand in hand, and she surprised me by going into the lounge instead of to the front desk or elevators. "I promised you chocolate."

"Yes, you did," I said as we sat down at a table...it being quite a disappointment it was going to be actual chocolate.

We ordered a bottle of wine and a chocolate dessert; I had read this evening incredibly wrong.

We were into our second glass of wine each, the dessert done... it was tasty enough, but it was only food... when she said, "So, I chatted with Carter today."

"Oh?" I asked, perking up.

"Yes, and he's willing to do a threesome with us sometime down the road, if you wish."

"I see," I said, having assumed that was what tonight was about.

She clarified, "To be clear, Carter is going to want you to suck his dick."

"I know," I said, my mouth watering at the possibility of making another fantasy come true.

"He also expects to fuck me."

"I know," I repeated, that idea equally as exciting as my sucking BBC. The idea of her getting the amazing fuck I couldn't give her, really turned me on.

"And you're still okay with all that?"

"As long as we're doing it together, and it's what you want, I'm okay with anything... the kinkier the better," I said as I felt her foot move to my crotch, and I therefore moved my hand to her nylon-clad foot.

"I'll only fuck young black men with big black cocks when you're there," she promised wickedly... even though it felt oddly romantic... as she slowly rubbed my caged clitty.

"And I'll only suck big black cock when you're there," I reciprocated.

"And eventually take it in that pussy of yours," she added.

"Well, that goes without saying," I said. "It comes under the banner of my doing anything that turns you on, because then it's guaranteed to turn me on, too."

"We can both explore some of our deepest, darkest fantasies."

"Nice pun," I laughed.

"I didn't even realize I was making one," she laughed, as she downed her second glass of wine. "Finish up. I have a pussy that needs fucking."

I wasn't sure if she meant hers or mine, as I downed my glass.

Joan poured, and then tossed down the remainder of the bottle, and we headed to the elevator. "I already checked us in."

"Cool," I said, as we held hands.

In the elevator, she pushed me against the wall and kissed me hard. The kiss was aggressive and passionate and urgent.

And long. It lasted until the elevator slowed down almost to a stop.

"Ready to get fucked?" she asked.

"Twenty-four-seven," I agreed, as the elevator door opened.

She led me to the room.

We walked in and I said, "Wow."

"I know," she said, and added, "Only forty bucks more."

"The bed is larger than a king?"

"Yeah," she nodded.

"A hot tub, too," I said, in awe of the room.

"And more wine," she said.

"Are you trying to get me drunk to take advantage of me?" I quipped.

"Maybe," she said with a smile, as she poured two glasses of wine.

"Well, play your cards right you masterful woman, and I just may let you fuck me," I replied playfully, as she handed me a glass of wine.

"Now get undressed, slut," she ordered.

"No foreplay?" I pouted.

"Oh, you want me to get undressed first?" she offered playfully.

"Yes please, and slowly," I suggested, sipping on my wine and getting a buzz.

She pushed me onto the bed, making me spill a bit of wine on myself, as she placed her foot on my leg. "Unbuckle me."

"Mmmmmm," I said, beginning high and stroking my hand down her silken calf.

I unbuckled the shoe, with a bit of work, and she ordered, "Take it off."

I did.

She switched feet, and I removed the other heel.

She moved away and slowly slid her dress down her perfect body. This time she was in a red lace bra with a matching garter holding up her mocha-coloured stockings. Her shaved pussy was on full display, as she wasn't wearing any panties.

"I think for now, the rest of this outfit stays on," she smiled.

"I definitely concur a million times over," I overstated my case, admiring her amazing body, the red lingerie really hot, wondering if red stockings would have been even hotter.

"Now get undressed," she ordered. "I have a dick that needs sucking."

"God, you always know just the right words to say," I said, as I quickly got out of my clothes, except for the all-white lingerie again... and of course, the cage I had absolutely no control over, yea or nay.

As I was getting undressed, she was getting her strap-on strapped on... this one bigger than yesterday's.

"Oh my," I said.

"We've got to keep working on stretching you out, so you can eventually take great big dicks in both of your holes, baby," she said, before adding, "and we have a way to go; most black cocks are bigger than this one."

"Makes sense," I nodded, as she walked over to the bed.

"Lay on your stomach and put a pillow under your caged clitty," she ordered, as she also pulled out an additional black dildo, also slightly larger than the previous ones.

"Yes, Mistress," I said, grabbing a pillow and getting into the position she ordered. In essence, my back arched and my ass up.... so my cunt was open for business.

"God, your girlish figure is just so fuckable," she said, as she moved onto the bed with lube and the dildo.

"Thank God you get to fuck it then," I said, "for both our sakes," loving her admiration of my body. What had always made me self-conscious before, now that I was in a sissy relationship, was an asset.

"Indeed," she said, as instead of feeling lube pouring down my ass cheeks, I felt her palms spreading my ass cheeks, and then felt her tongue on my pussy.

"Oh yes, eat my pussy," I said, loving the feeling of her wet tongue and hot breath on my backdoor entrance.

"Such a delicious pussy," she purred, as she really tongued my hole.

"Not as tasty as yours," I moaned, her tongue working its magic on my entire body, including my confined clitty.

"Well, that goes without saying," she said as she kept bathing my pussy with warm wetness.

"God, that feels good," I moaned.

"Need to get it nice and ready for this big black vibrating plug," she said, as a finger rather easily slid inside my pussy... no resistance at all, unlike her previous fingerings. "Your pussy seems pretty hungry."

"It's always hungry," I admitted, as she wiggled her fingers around, just grazing my prostate.

"God, you're a bigger slut than any girl I know," she said, which should have been an insult, but instead I took as a compliment.

"I want to be the biggest, sexiest, sissy slut I can be," I said, my declaration so pathetic, and yet so earnest.

"Mmmmmmm," she purred, as she kept fingering me as she poured lube down my crack. A moment later, she pulled her finger out and warned, "This may spread those pussy lips quite wide."

"Okay," I said, ready for the pleasure and pain principal to begin its work inside me.

I felt the toy at my entrance, and then I felt it slowly slide inside me. "Ooooooooh," was the sound escaping my mouth, although I wouldn't call it specifically a scream of pain or a moan of pleasure, but somewhere in between.

"God, your pussy loves dick," Joan said, as she seemed to be watching with pleasure as the black snake slithered inside me.

"I love it so much," I admitted, and even added, "I can't wait to feel a real black cock filling my cunt."

"All in good time," she said, "all in good time. That's what everything we're doing right now is preparing you for." Then she slapped my ass. Just once, but unexpectedly and hard.

"Yes, Mistress," I yelped, the slap harder than any of her previous ones. I apologized in case I'd offended her, "But both my holes are owned by you first."

"Don't forget that," she said, as she began slowly to pump the dildo in and out of my pussy.

"And my clitty too," I added, as my pussy got fucked again, making my clitty once again desperate to salute my beautiful, dominant, Mistress.

She pushed the dildo deep inside me and said, "All right, now let's practice your dick sucking."

"Okay," I said grimacing in sudden pain, as the dildo went deeper than any other cock inside my pussy.

"Now to make this even more fun," she said, as she went to her duffel bag of sexual surprises.

"You have me curious," I said, as I saw a remote control in her hand.

"Let's start this on low," she said, "we don't want your tiny clitty making a big mess quite yet."

"Not in this cage it won't," I said, trying to hint she could take it off me, although the hint went unacknowledged, as I felt soft trembling inside my pussy.

"And now let's really have some fun," she said, approaching me with a blindfold.

"Why a blindfold?"

"Why not?" she said. "Plus, when one sense is blocked, it enhances your other ones."

"Okay," I agreed, not that I really had any choice in the matter.

She put the blindfold on me and said, "Now just do what comes natural."

"Yes, Mistress," I said, finding the blindfold a little unnecessary, and yet somehow a little stimulating too... I felt even more helpless than before, which was a surreal turn-on.

A moment later, I felt her plastic cock touching my lips.

I opened them automatically, and took the head of her cock in my mouth.

"Mmmmmm, you love having something in your mouth, don't you?"

I replied, as I swirled my tongue around the cock head, "I love having a cock in my mouth."

"You look so pretty like this," she said. "Ass up, nails painted, in virginal lingerie, something in your cunt and something in your mouth."

"Maybe I also need lipstick and a wig," I mindlessly suggested, not even realizing I was requesting a more extreme version of femininity.