Sissification 101: Ch. 05

Sissification 101 Ch 05

Summary: Erica practices taking BBC in both of her sissy holes.

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 by a very supportive girlfriend in pantyhose watching hypno-sissy porn.

Sissification 101 Ch 02 tells how 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 tells how Eric is pegged for the first time by his girlfriend.

Sissification 101 Ch 04 tells how Joan rents a hotel room for their first black cock for both of them. Eric(a) sucks his/her 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) dining on his first BBC creampie.

8. PRACTICE MAKES PERFECT

SUNDAY

The next morning we ordered room service and enjoyed each other's company as a couple.

It wasn't until we were checking out of the hotel that Joan said, "So this week you'll be practicing on your own, in both of your pretty pleasure holes."

The new term 'pleasure holes' made me smirk, yet I asked, "On my own?"

"You do remember I'm flying to New York this afternoon?" she asked, her tone implying she wasn't impressed by my forgetting.

"Oh, shit," I said, suddenly remembering. "I completely forgot. I've been a little preoccupied."

She smiled forgivingly, "I guess you have been distracted."

"A little," I joked.

"And soon a lot," she smiled, as she held her hands apart to show at least ten inches.

"I can't wait," I admitted, knowing that next weekend I'd be getting fucked by Carter. And I certainly hadn't forgotten that!

"You'll have to," she said, slapping my ass. "And that pussy is in word-of-honour training until I return."

"I understand," I nodded.

"And you're welcome to suck Carter's big black cock whenever the opportunity arises," she offered generously.

"When do you get back?" I asked, thinking even a single day would be too long.

"Saturday afternoon," she said.

"Fuck, that's an eternity," I sighed, sounding rather pathetic.

"Use the time to practice sucking cock and fucking that pussy," she suggested.

"I will, but it won't be the same without you," I said, thinking I may need my own suction wall cock.

"Well, that goes without saying," she said.

"I figured I'd say it anyway," I smiled.

"You're a keeper," she said, kissing me. "But I need to get you home."

"Fine," I said, in the way women usually said it, when it wasn't fine at all.

"Don't pout, little girl," she said as we walked to her car. "It's not becoming."

"I'll just miss you."

"I'll miss you too," she said. "And we can chat in the evenings when possible, and keep your training going."

"Okay," I said, that making me feel better.

"But I need to go hike and pack," she said. "I'll be taking a couple toys with me, including that heavenly one you bought for me."

"I may go toy shopping myself," I said.

"Carter is working this afternoon," she said. "In case you're hungry."

"I may have room for a little snack this afternoon," I said coyly.

"There's nothing little at all about that treat," she smiled.

"True, it's like a full meal deal," I joked, imagining myself servicing that big black cock again.

"Mmmmmm, now you're getting me hungry."

"I'm getting myself hungry too," I said, already knowing I'd be heading to the sex shop this afternoon.

Once we got to my place she told me, "I need to go pack, and you should go and suck some cock."

"I think I will," I nodded.

"I know you will," she leered, giving me a kiss.

That afternoon, I drove to the sex shop with two purposes: to get a black suction cock dildo, and to suck Carter's cock (although not necessarily in that order).

The entire drive, I couldn't wait to get there.

Then... I got there.

And got cold feet; was I really going to an adult store to suck a black cock?

Obviously the answer was yes, but without Joan, I suddenly felt pathetic. Yes, I also had hints of feeling pathetic when I was with Joan, but they weren't nearly as bad as this. With her, I had an accomplice. I had a purpose.

So I sat in my car for a full twenty minutes... almost exiting a few times, and almost driving away a few times, yet really doing neither.

I was completely paralyzed with indecision.

I felt like when I was sixteen and wanted to ask out Sarah (my high school dream girl), and almost did a hundred times, but fear kept me from ever saying a word. Which left me with a regret that lasted a long time, especially when I learned years later that she'd liked me too.

Joan, apparently able to read my mind even when she was nowhere near me, called and asked, "Where are you?"

"In my car," I answered.

"And where is your car?" she asked, already knowing where I was.

"In a parking lot."

"In front of a certain shop?" she asked coyly.

"Maybe," I responded playfully.

"How long have you been just sitting there?" she asked.

"Half an hour, give or take," I admitted.

"What's stopping you?"

"You're not here with me," I admitted.

"I am in spirit," she supported.

"I guess," I said.

"Go in there right now," she ordered.

"Is that an order?" I asked, smiling to myself.

"Get the fuck in there, buy something large to fuck that cunt of yours with, and suck some black cock," she ordered firmly.

"Yes, Mistress," I obeyed, loving her dominant persona, immediately getting out of the car... her words of encouragement all I needed as I continued to explore the new me.

"I'll be calling Carter later, to find out if you obeyed," she surprised me.

"I'll obey, Mistress," I repeated, before adding the cold hard truth, "I'll always do anything you order me to do."

"Like a good girl," she replied soothingly.

"Yes, Mistress, like your good girl," I agreed, as I walked (now happily) to the store.

"Have fun," she said, her voice all sing-song.

"Oh, I will," I said, now feeling much more confident about my decision to go through with this.

"Love ya," she sang, and hung up before I could echo her sincere sentiment. In many ways I was an emotional wreck as I explored my new sexual horizons, which at many times were wonderfully intriguing, but at others were horribly frightening. But beneath everything else, like a secure bedrock, lay my love for, and my trust in Joan; and even more empowering was my knowledge of her love for me. It's true that she often humiliated me and called me degrading names, but we both knew that although she thoroughly enjoyed playing the role of imperious Mistress, she wouldn't be doing it if she wasn't confident that ultimately such treatment made me happy.

I entered the store and saw a girl at the till, who greeted me. Although her greeting was warm and friendly, I felt an instant rush of disappointment. Yes, I was nervous about sucking cock on my own, but my core reaction when suddenly the possibility was taken away from me, was utter disappointment.

Yet I'd also come here for another reason, so I headed to the dildo section. Fuck, there were lots of them.

After a short while I was just browsing aimlessly, when the girl approached me and asked, "May I help you with anything?"

Figuring fuck it, shame no longer an emotion I was supposed to have, so I was trying to suppress it at all times, I mustered the courage to answer. "Yeah, I'm looking for a dildo that sticks to a wall."

"I see," she said, as she asked, not at all put off by my request, I imagine they get all kinds of questions and weird people in here (I never thought I'd be one of those people, but here I was), "Is it for you, or a lady friend?"

Shame coursed into my cheeks, something I couldn't control or suppress for even a moment, as I admitted, "It's for me."

"And are you new to prostate stimulation?" she asked smoothly, describing my taking a cock in my ass or pussy in an extraordinarily politically correct fashion.

Deciding to be open about how pathetic I was, I replied, "My Mistress has been training my back end for a week."

"Which must mean your sphincter isn't very stretched out yet. So are you looking for girth, or length, or both?" she asked, again not seeming at all fazed by my sexual practices, and happy to discuss my goals in clinical terms, very much like a nurse might do.

"I'm expected to take ten inches with ease by next weekend," I answered, as Carter's big black cock popped into my head... an image I imagined was now etched into my brain for eternity.

"Lucky you," she smiled, this time not at all clinically but rather flirtatiously for a moment, as she selected a big black cock from the wall. "This one is ten inches long, thick, and quite realistic."

"Oh my," I said. It was surprisingly heavy... and the veins felt real.

"It is however, not an adequate substitute for the real thing," a male voice observed from behind me. A deep voice I instantly recognized as Carter's.

"Well, that goes without saying," the girl smiled... definitely flirtatiously.

"I'll take care of him from here, Anna," Carter said.

"Sure," she said, although I couldn't tell if she had any clue why Carter was taking over with me.

Once she was gone, Carter said, "She made a good choice. This one will get that pussy of yours somewhat ready for the real thing."

I could feel my face burning with shame yet again, before I quietly said, "Good, I'll take it."

"Oh, you'll be taking it all right," he smirked.

"Um, I, could I.... please..." I babbled, unable to force out the other thing I'd come for.

"Are you hungry?" he asked, able to understand the purpose behind my incoherent babble.

"Very much," I nodded, beginning to wonder just how transparent I actually was. Joan could always read what I was thinking, today from a long distance, and now so was Carter.

"Follow me," he said.

I did, still carrying the ten-inch black toy as I followed, my clitty tingling in its cage with anticipation.

We went into the back room which was small, but plenty large enough for what I was about to do. He snapped his fingers, and I dropped before him as quickly as if I'd been knocked down.

"You really are one of the sluttiest cock suckers I've ever met," he said, as I knelt before him.

Proving that statement correct, and feeling more like my Sissy self now that I was on my knees and alone with him, I asked, "May I please take out your big black cock and suck it?"

"Go ahead; but I only have a few minutes, so get to it," he ordered.

I quickly reached my hands to his pants, unzipped him, pulled down his pants and then his underwear, revealing an already semi-erect cock.

God, did this black cock excite me as my clitty tingled, my mouth watered, and a chill went up my spine, as I reached out and stroked the thick dick.

"Get sucking, faggot," he ordered a couple seconds later, as I was busy just admiring the sheer majesty of his cock.

"Yes, Master," I replied, taking his cock in my mouth.

"Just so you know going forward, here's a ground rule. When you're here with Joan you're a feminine slut, but when you're just with me, you're a cock sucking faggot, is that clear?" he informed me as he hardened in my mouth.

"Yes, Master, I'm just a cock sucking, cum taking faggot for your pleasure," I agreed, lust consuming me as it always did when I saw a black cock, and belittling myself enhanced the situation.

His cock now hard, I took it back in my mouth and bobbed like the faggot I was for him.

"You're a natural dick smoker, faggot," Carter groaned, as I bobbed furiously, taking over half of his big black cock. Progress!

I loved the compliment, thriving on the knowledge I was doing a good job. I loved licking a woman and hearing her moans, her wicked words, and her scream of euphoria when she came and coated my face. So not surprisingly, I loved hearing his moans, his wicked words, and couldn't wait to feel another load all over my face, or perhaps to taste my first full load of cum.

I kept bobbing for a couple more minutes, my clitty desperately trying to break free of its cage while my attention was completely focused on serving this cock, on pleasing this cock, and getting his cum.

"Oh yeah, don't slow down, you fucking cock sucking faggot," he ordered, his moans telling me he was close.

I had no intention of slowing down until his load was either on my face, or in my mouth.

I wanted both.

"Want to taste my load, slut?" he asked as he pulled out.

"Yes Master, I'm dying to taste your cum," I admitted, as he furiously stroked his cock.

"Open wide," he ordered. "Catch it all, but don't swallow it."

"Yes, Master," I said, before opening my mouth wide for his target practice.

Seconds later, his cock shot rope after rope directly into my waiting mouth.

When he was done he ordered, "Close your mouth and swish my cum around in your mouth. Savour the taste, the texture."

I obeyed, surprised by how salty it was... and how the texture was so gooey and Jell-O- like.

The taste was instantly satisfying... addicting.

"Get used to the taste," he said, as he put his cock away. "You'll be eating a lot of cum."

I kept swishing the cum around in my mouth...like I was savouring a mouthful of fine French wine.

"Give me your phone," he ordered.

I mindlessly handed it to him, oddly not at all worried about what he would do with it.

"Open wide and show me that little lake of cum," he said, as he moved the phone up to take a closeup photo of me with a load of cum in my mouth, completely hiding my tongue.

He snapped a couple of photos, and handed my phone back to me saying, "I'm sure Joan will appreciate seeing these."

I closed my mouth to savour his cum some more until he said, "You may swallow it."

I swallowed, the cum sliding down my throat, and into my belly. I imagined this being the first of many.

"Thank you, Master, that was delicious," I said, sounding pathetic and faggoty (I know that isn't a word, but it seems to fit perfectly in this instance).

"Tomorrow evening between five and seven," he said.

"I'll be here," I said, excited to be getting another load tomorrow.

"Of course you will," he said, as he then added, "now go pay Anna for your new dildo."

"Yes, Master," I said, getting off my knees and following him out.

I picked up some lube too, and went to pay Anna, who was at the counter.

"Get everything you came here for?" she asked.

"I definitely did," I said, Carter's cum aftertaste still lingering in my mouth.

"Good," she said, as she rang up my items.

"Thank you," I said, when she handed me my items in a discreet brown bag.

I headed out to my car and once inside, looked at the photos. The first one was slightly blurry, but the second was unmistakable. The cum filling my mouth couldn't possibly be anything else, nor could my position on my knees be easily explained as anything else than the reality of what it was.

I texted Joan, with the attached picture: I just swallowed my first load of cum.

She responded: Yummy. I assume you enjoyed it.

I responded: I see why you like it so much.

She responded: Cock cum or cunt cum... which do you prefer?

I responded: They are both necessities of life.

She responded: I'm looking forward to comparing the two soon.

I responded: I'm looking forward to seeing that too.

She responded: At the airport and about to go through security.

I responded: Love you.

She responded: I love you too. Be sure to work that pussy.

I headed home, and after dinner I pulled out the new toy. I got undressed, lubed up the new toy, stuck it to the wall in almost the exact same location as Joan had earlier, and awkwardly backed myself up to the black cock.

I moved blindly around until I could feel it at my pussy, and I pushed.

Nothing.

I pushed back again, and still nothing.

I tried a third time, and I still couldn't get it inside.

Frustrated, I gave up.

I ended up realizing I likely had to loosen up my pussy with smaller cocks first. But I decided, since I was pretty tired, I would work on that tomorrow.

I received a text from Joan that she had arrived safely and would call me tomorrow.

MONDAY

Other than secretly wearing my panties and pantyhose, the workday was just that... a workday.

I arrived at the adult shop precisely at five, and the same girl Anna was working there. I sheepishly said, "I think I'll need something smaller to begin with."

She smiled, "Yes, after you left yesterday, I thought that one might be a bit ambitious."

"It definitely was," I admitted.

"I'll show you some others," she said, leading me back to the same section as yesterday. "This one is almost as long, but narrower."

"I like it," I said, taking the thinner cock, but also excited to feel eight inches inside me.

"I'm sure it will do the trick," she said.

"I hope so," I said.

"Can I help you with anything else?"

"Um, is Carter here?" I asked sheepishly, assuming she'd know why I would ask that.

"He's in the back room," she said. "I'll let him know you're here to see him."

"Thank you," I said, not seeing anything in her demeanor to indicate she had any clue why I was asking for him.

She went into the back room, returned a moment later and said, "You may go back now."

"Thank you," I said.

"I'll hold this for you at the till," she said, graciously taking the toy from me.

"Thank you," I repeated, as I returned to yesterday's scene of the crime.

"Right at five, you must be pretty eager," he said.

"This is on my way home from work," I said, although truthfully it was more like twenty minutes out of the way.

"Well, get to work," he ordered.

I walked over to him, dropped before him, fished out his cock, and went to work. My goal for today was to take at least eight inches into my mouth.

"Today, I want you to take your time," he said.

"Yes, Master," I nodded, as I admired his cock, which was completely flaccid.

"Get him hard first," he ordered.

"Yes, Master," I repeated, as I swirled my tongue around his thick cock head. Appreciating the idea of his cock being referred to with a male pronoun.

"Lick your way down the shaft," he instructed, "and go to my balls."

"Yes, Master," I said, slithering down his thick shaft with my tongue before reaching his big black bag. Fuck, even his bag was impressive. So dark. And undoubtedly full of cock cum.

I wasn't really sure what to do, so I just licked the bag, which had a strange texture and seemed delicate.

"Suck each ball into your mouth and stimulate it," he instructed me.

I was tentative, as I didn't want to hurt him or bring him discomfort in any way. It was awkward as I took the bag into my mouth and felt around for a ball.

Once I found one, I was shocked by how big it was.

Hard, and yet soft.

"That's it, bathe my balls in that cock sucking mouth of yours," he said, making me feel a little better that I was doing something right.

I licked.

I sucked gently.

I swirled my tongue around for a bit.

I went back and forth between balls.