Sissification 101: Ch. 02

"Don't worry, I'm still planning on using your tongue regularly," she promised, I noticed not mentioning my tiny penis in this context.

For a few minutes... her moans continued... slowly building... as the toy did its magic... and I ate her asshole.

Eventually she ordered, "Now move up and lick my pussy, baby."

I eagerly obeyed, licking her pussy as she readjusted the toy slightly to provide me access, while the toy still worked her clit over. She'd been at this for a while and she hadn't come yet, so I guessed the saleslady's point about a long, slow build was valid.

"Oh fuck, yes, so fucking good," she moaned, as it was obvious she was finally getting close. I kept licking her wet pussy until she screamed, "Holy Jesus Christ!"

Her cunt cum gushed onto my eager lips and tongue, as I lapped up every drop.

Her orgasm did indeed appear to be endless, but eventually she moved the toy away as she was still trembling uncontrollably.

I continued licking until she pushed my head away and said, "I've got to pee."

She bounced up and hurried to the bathroom.

I rolled off the bed myself, the toy still making it pretty awkward, but now with hardly any pain at all, and called out, "Are we finishing the movie?"

"Yes, I'll meet you down there," she called back.

I headed downstairs, this time just needing the railing to steady myself a bit, grabbed us a couple drinks, and sat down (without yelping or flinching), ready to finish the movie.

She rejoined me a minute later, with her panties from yesterday in her hand, "I found these under your pillow."

I felt my cheeks go red, but admitted, "Yeah, I kinda slept with you last night. I love your scent."

"That's one of the sweetest thing a man has ever said to me," she said. She then surprised me again. "Put these on."

"Really?" I asked, as she tossed them to me.

"Yes, I think you'll look cute in them."

"Okay," I agreed, yet again getting those simultaneous contrasting feelings of excitement and humiliation.

I stood up slowly as the plug shifted in my pussy, peeled off my pantyhose, which was much more work with a plug moving around inside and slightly stimulating me. I put the panties on.

"I was right; you look really cute in my panties," she approved.

"Thanks, I guess," I said, not sure how to feel about a compliment like that.

"Wear them to work tomorrow under your pantyhose," she ordered.

"Okay," I agreed as she moved back to the couch.

We sat back down, me doing it slowly but far more painlessly, and as she cuddled into me, she said, "By the way, my new toy is, without a doubt, the best present ever."

"You're welcome," I said, as she squeezed my penis through her panties.

Once the movie was done and she was heading home, having explained weeks earlier that she shouldn't sleep over during the work week, and as she got ready to leave, she returned to her witty self, using one more Beatles title, "Be a good girl and we'll come together; just not right now."

5. CAGED... BBC FORESHADOWING

Thursday

I texted Joan after really struggling to get comfortable with the plug in my ass, and becoming nervous about it affecting me enough to interfere with my work, and/or my professional demeanor: Hey, babe. I want to obey you without hesitation, but I'm a little uncomfortable about going to work with a plug this size in my ass.

She responded a couple minutes later: I understand. We need to take baby steps. Just make sure you're in pantyhose and my panties.

I responded, thankful she was so understanding. I imagine that will be a forever daytime thing now.

She replied: Yes, it will be. It's all part of your feminine transition. PS: we are going shopping after work.

I asked: For what?

She texted back: Pets don't ask so many questions. Just bring your butt plug with you. We will need it while shopping.

I replied: Yes, Mistress.

That last order scared me a bit, but as always, it also excited me.

Joan was as much of a sexual deviant as I was, which was what made all of this so thrilling. I had found her, in the iconic words of Phoebe Buffay, 'my lobster'.

The day was again crazy busy, like they all seemed to be recently, and other than passing her in the hallway, or waving to her as I walked past her office, I didn't see her all day.

Before I had been caught in the act last Monday, that was the norm and no big deal... work was work and after work was after work, yet now all I could think about was her... and Friday... but first, there was shopping.

She called me moments after work and reminded me, "Don't forget to bring your butt plug with you."

"Already ahead of you. It's in my briefcase... with the lube." I answered.

"Be at the Westlake Mall at 5:15," she said. "Front entrance."

"Leaving soon," I said.

I finished up a couple of emails, picked up the bracelet, and drove over to the mall. I was going to be quite early, when an idea popped into my head. I should put the plug in my cunt before meeting her. The mall was nowhere near where I lived, so I felt the odds of running into anyone I knew were slim... and I wanted to surprise her.

I pulled into a coffee shop, ordered a coffee, I felt I couldn't just use their bathroom without ordering anything, and then before picking it up, went to the washroom.

I went into the only stall, opened my briefcase on the top of the toilet tank, undid my belt, waistband and fly, and then pulled down my pants, pantyhose and panties. I grabbed the lube, and coated the toy very generously. I then dribbled some down between my ass cheeks, realizing this was more challenging on my own... doubled by my being in such a confined space.

I grabbed the lubed up toy and moved it to my ass... my cunt. I pushed, and nothing happened. I pushed again. Nothing.

It was just too awkward, and I didn't have any leverage.

Suddenly the door opened, and a guy went to the urinal. I quickly turned around and sat down on the toilet seat. That's when an idea came to mind.

I waited for him to finish... thankfully he didn't wash his hands... gross, but it meant he left sooner.

I then placed the plug on the closed toilet seat, after distributing excessive toilet paper on the seat first... grasped the plug with one hand, and slowly lowered myself onto it. It was still awkward, but thanks to the weight of my body, following a brief resistance, it slid inside me.

"Ooooh, fuck," I moaned loudly, as I settled myself completely onto it.

It burned.

But it wasn't as bad as last night, I was feeling a tad more pleasure than pain, so overall it felt amazing.

A rush of sexual adrenaline at the reality I was sitting on the plug was exhilarating.

I slowly stood up, quickly pulled up my panties, pantyhose, and then my pants. I screwed the lid back on the lube, closed my briefcase and went to pick up my coffee... realizing it had been a good five minutes since I'd ordered it.

I grabbed it and explained to the girl, as I walked awkwardly, again getting used to this (only medium sized!) plug in my ass, "Sorry, I'm not feeling too well."

She nodded and turned away unbothered, and I walked clumsily out of there feeling so slutty, knowing I had a plug in my pussy. Weird how much feeling slutty turned me on.

I drove toward the mall, feeling even more full in this sitting position, there's really only one way to sit while you're driving, no choices, and in my case pleasure and pain battling for dominance inside me, and arrived.

Joan was standing outside the mall entrance, speaking on her phone.

She was dressed in a very cute blue dress, with dark beige nylons that had my penis hard the moment I saw her.

She smiled when she saw me approach, raising her dress to show me her thigh highs, "Like?"

"Love," I amended.

She looked at me a moment and asked, noticing my awkward movements, "Do you have the plug in your ass already?"

"My cunt," I corrected, and then added, "You told me to bring it, but not how to carry it."

"Well, that that clever little act of adaptive obedience solves my first problem," she approved, leaning in and kissing me, while reaching around and slapping my ass playfully, right on the base of the plug. Ouch! "I wasn't sure how we were going to get that plug back in your cunt."

"Ohhhh," I moaned and groaned, a mixture of pleasure and pain coursing through me, and her calling my ass a 'cunt'.

"Let's go," she said. "We've got a lot of shopping to do."

"A lot?" I asked, as she took my hand.

"A lot," she affirmed, as we entered the mall.

I had imagined our going to some discreet adult shop, so I was quite surprised when she marched me into a Victoria's Secret. It was a store I'd walked past many times, jerked off to their catalogs a few times, but had never actually gone inside one... I just thought a lone guy going into a female lingerie shop, unless he was on a specific errand for someone, was too pervy.

"I thought we were buying a cage for my tiny penis," I said timidly, "Are we here for you or me?"

"You," she said before giving me a quick kiss and adding, "and a little bit me." She kissed me again and added, "But mostly you."

"Uh, okay," I said.

"First, we need to get you some sexy panties of your own," she said, leading me to the panties area. "We can't have you wearing mine all the time."

"Um, okay," I repeated, unsure of what else to say.

"Any colour you'd prefer?" she asked as we reached an acreage (well not quite that large) containing an abundance of sexy lingerie.

"No, not really," I said, as I scanned about a half dozen different styles in a large spectrum of colours. Truth was, I imagined myself wearing pink in all my fantasies, because that's the most girly colour, which is also to say the least manly. So I blurted out, feeing my cheeks going a little red, "Well actually... pink."

"Definitely getting you some pink ones," she said, pulling out a lacy pair.

"And light blue," I said, that being my favourite colour on Joan.

"These would look so cute on you," she said, holding a pair of light blue panties in her hands. "Feel them," she said.

I reached for them, and was surprised by how much softer female underwear were compared to male underwear. "They're super soft."

"I know," she said. "Oooooh, these," she squealed.

They were black, and a thong.

I'd never understood thongs. I couldn't understand how they could possibly be comfortable, although they were indeed sexy to see on a woman. Anytime I saw a thong peeking out of a woman's outfit, I just assumed she was kinky. I know that's shallow stereotyping, but it's just how my brain works.

"I've never seen you in one of these," I said.

"I have one," she said and then whispered into my ear, "but I only wear it for special occasions... like tomorrow."

"Mmmmmm," I moaned at the idea.

She whispered in my ear, "Pick out six pairs. One has to be white. I need to go find something special."

"Okay," I said, "What size?"

"Well, you fit pretty well into my panties. So I'd imagine a medium," she said.

"Okay," I said.

She kissed me and disappeared.

I looked through the panties, feeling kind of like a pervert, since I was now standing all alone in a Victoria's Secret.

I had four pairs in my hand, when a salesgirl showed up, asking, "Do you need any help, sir?"

"I-I-I," I stammered, feeling, and probably looking, like a kid caught with his hand in a cookie jar.

"Have you got six yet?" Joan asked, returning.

"Almost," I said, saved by the bell.

"If you need any help, just let me know," the girl said, and walked away. Evidently, so long as I was accompanied by a female chaperone, I wasn't a threat to public morality.

"Think she knows they're for you?" Joan asked.

"I hope not," I said.

She grabbed two more pairs for me and said, "Now we need you to pick some lingerie for tomorrow's special occasion."

"For me?" I asked.

"Yes," she said, again whispering in my ear. "Doesn't my sweet Erica want to look sexy for her Mistress tomorrow?"

"I-I-I do," I stammered, her hot breath turning me on.

"Maybe something bridal," she whispered. "In this arena you're virginal, you know."

I imagined her someday wearing white for me... all white... yet, we hadn't even said our first 'I love yous', although I planned on attending to that tomorrow. Now she was imagining me in all white. I joked, "You haven't even proposed yet."

She smiled, as she again whispered in my ear, "I'm proposing a whole new world."

"Okay," I agreed.

She took my hand and led me to the back of the store. "I was thinking a complete lingerie set."

"I'm always thinking that," I responded slyly.

"I'll be wearing something so sexy for you tomorrow night, your little clitty will be begging for release from its cage. An outfit that will symbolize our new hierarchy," she said.

"What will that be?" I asked, my tiny penis flinching in my panties and pantyhose at her naughty promise, as well as her derogatory little attack on my penis.

"It will be a surprise," she said, before pointing towards an entire lingerie section. "Do you like any of these?"

"All of them," I said, every outfit sexy as fuck. Every one of them was either a garter belt, or had the pieces to clamp stockings to, including: lace camisettes, a front zipper corset, a cute teddy, a bodysuit. (Actually, nobody would attempt to attach stockings to a camisette, so they were exempt from the rule.)

"They're all super sexy," she agreed as she squeezed my ass, reminding me I had a plug stuck in it, as she whispered ever so sultrily, "I think you'd be pretty fucking hot in that corset." She pointed to a red lace piece.

"I couldn't tell without seeing it modeled by someone," I said, thinking maybe I could convince her to try some of these outfits on.

She smiled, "You sly dog. You want to see me looking all sexy in some of these?"

"I'd like to see you in all of them," I flirted.

"Well, since we have similar body types," she said, yet another shot at my feminine body. "It could help us decide what to get you."

"Yes, yes it most definitely would," I agreed with great enthusiasm.

"Well, pick four more while I go try this corset on, and I'll model them for you," she offered.

God, I loved this woman.

"Will do," I agreed.

She gave me a kiss and sauntered off to a change room. I was bewildered at first by the overwhelming number of choices, but started looking around one outfit at a time, and chose four more sexy lingerie pieces... wondering what the lace lingerie would look like on her, and feel like on me. I didn't even see her walk past me as she left.

I found her change room, thankfully the store was relatively deserted, and she walked out in a red corset seconds later, and somehow she'd found red stockings to go with it.

"Wow," I gasped. I'd never seen anyone look more beautiful than she did at this moment.

"So, you like it?" she beamed.

"'Like' is like the biggest understatement in the world," I responded, feeling like I might be drooling.

"What else do you have for me to try on?"

"These," I handed her, unable to tear my gaze away from her.

"Grab me some black, white and beige stockings," she instructed.

"With pleasure," I said, still staring at her.

"I think you'll look pretty cute in the one I'm wearing," she said.

"I couldn't possibly do justice to it like you're doing," I said.

"You're so sweet," she said, kissing me and returning to the change room.

I adjusted my tiny penis, and went to find the stockings. I grabbed the colours requested and returned.

"I have them," I said.

"Pass them over the door," she said.

I did.

I waited.

A couple minutes later, she came out in an all-white teddy that held her firm smallish breasts perfectly, came together between her legs, and was attached to white stockings.

She looked like a bride about to consummate her marriage.

"Wow," I said again.

"Look," she said, glancing around to check we were alone, before she flipped open a flap at her crotch and pointed out, "It's crotchless."

"Oh my," I said, looking at her shaved pussy, framed by that oh-so-sexy outfit.

"Yes, easy access," she smiled.

"Wow," I said, just in awe of her.

"I think we know one that we have to buy already," she said.

"All of them," I joked.

"Why not?" she shrugged.

"Exactly," I laughed.

"I'll try on one more, though."

"Just one?" I asked with a pout.

"For now," she said.

"Okay," I agreed.

She disappeared again, and I waited for her to change. She came out eventually, wearing one that was ridiculously hot, and a little dominant.

All black.

A zipper in the front that gave her limitless options for how much cleavage (or navel) she could show.

Black stockings.

"I may be repeating myself, but wow," I said.

"I think I'll just keep this one on for now," she said, as she pulled the tag off of it.

"Forever?" I joked.

"Maybe," she winked and returned to the change room.

I waited for her to come back out, we paid for all the panties, lingerie and stockings, and headed to her car.

"One more stop," she said. "Get in."

"But my car?"

"I'll drop you back off after I'm done with you," she said, squeezing my penis.

"Okay," I groaned, my penis desperate for release; but that wasn't happening until tomorrow night.

We drove for about ten minutes as she chatted about work and a new merger she was working on. I talked about two clients I was trying to reel in.

We arrived at a strip mall with an adult store.

"Let's go get you a cage for that tiny penis of yours," she said, as she squeezed said penis.

"Yes please, Mistress," I agreed.

We walked into the store as she joked, giving my hand a soft squeeze, "As much as I spent here a couple days ago, plus whatever we spend today, they should start giving me a 'preferred customer' discount."

"Who knew the road to being a sissy faggot would be so costly?" I joked.

"Yeah, who knew?" she agreed, as we entered the store.

Unlike Victoria's Secret, where Joan had been largely discreet, and I think anyone paying attention would have assumed every purchase was for her... she wasn't at all discreet here. She asked, ironically, a young bald black man looking to be in his early twenties, "Where would your dick cages for my honey be?"

"I'll take you there, ma'am," he said, as if the request wasn't the least bit strange, even as he gave me the twice over. It made me wonder how many people came in here to buy cages. I couldn't even begin to come up with a figure. Was it miniscule? Huge?

Yet, like the store I'd gone to, there was an entire section with just cages.

"Oh my," Joan said, I think as surprised as I'd been by how many different kinds there were.

"Is it for him?" the black guy asked point blank, speaking to her and ignoring me, except as something to point at. He knew already who was in charge in this relationship, which was again a little humiliating, but we were here for a penis cage, so I was far past objecting to any amount of humiliation.

"Of course," Joan nodded, I'm sure my cheeks the brightest red they'd ever been. I lowered my gaze, avoiding eye contact with either of them.

"I see," he said. "Is the purpose discipline?"

"Kind of," she said, as I looked up. "He's in training of sorts. I want him caged, but..." she paused as she examined a device that looked like a miniature iron maiden, spikes and all, "I don't want him in pain."

"Okay," he nodded. "There are quite a few options for that."

"Great," Joan said, clearly excited... which excited me.

"I recommend a metal one, although plastic ones are available as well," he explained.