Sissification 101: Ch. 02

I straightened myself up and pulled up my pants, my penis fully erect.

Joan noticed and reminded me, "Don't forget, no getting yourself off."

"That'll be hard," I replied.

"Terrible pun," she groaned, this time not in a sexual way, sitting down at her desk.

"Maybe you should cage my penis," I said slyly, realizing that was the one thing I hadn't thought to include in my lengthy fantasy list last night.

"We'll see. Maybe I'll have to, if you can't leave your tiny clitty alone."

"I'll try my best," I said, although after this experience, it was going to be very difficult. I also noticed she was beginning to make a point of commenting on what I'd always known... my penis is small.

"There's no trying," she said, as she propped her shoeless nylon-clad feet on her desk. "There's just doing."

"Are you trying to get me horny with that sexy display?" I joked, my cock having flinched instantly when her nylon-clad soles popped into view.

"If you come, then I won't wear these for you anymore," she said, wiggling her toes. "And you wouldn't like that."

"No, that would be a travesty."

"Then be a good girl and obey."

"Yes, Mistress," I replied, knowing I was all hers now, and would do pretty much anything she ever told me to.

"I'm off to have dinner with my mom tonight," she said. "So I'll see you tomorrow."

"Definitely," I said, as I started to walk... and was brought up short for a moment by the plug in my ass.

Then later on, twice I sat down and flinched, forgetting about my butt plug; otherwise it wasn't very noticeable... I imagined tomorrow's would be thicker and longer.

I didn't turn my computer on at all that night, so as not to be tempted.

Instead, I caught up on the last five episodes of The Blacklist I'd been taping... nothing sexy about that show... and went to sleep...ignoring the silent pleas from my needy little penis.

4. A GIFT FOR JOAN

Wednesday

I woke up, rolled over, and was reminded of the plug in my ass.

I went and showered, got dressed, no underwear but yes pantyhose again, and headed to work... although I had two meetings with clients at their own offices, so I didn't get to my own office building until after lunch, and therefore didn't see Joan at all... until the work day was over.

I got a text from Joan: Sorry, working late. I'll stop by your place later tonight.

I replied I'd be home by seven, not mentioning it was so I could stop to pick up a bracelet I'd ordered and gotten sized to give her on Friday... with the date we'd first met inscribed on the inside. (I was pretty sure keeping secrets about special presents for her was allowed.)

Unfortunately the bracelet wasn't back from the engraver's yet, but they guaranteed to have it for me by noon tomorrow. I then headed to an adult store. I wanted to give her something sweet and romantic at dinner when I told her I loved her, but I also felt compelled to buy her something sexy for when we got home, especially after all that had happened between us recently... even though I had no idea what Friday's fun and games were going to look like. Except for the part when she took my anal cherry, of course.

I reached the store, went inside and walked around... not even sure what I was looking for... just hoping I'd know when I saw it.

Before I knew it, I was standing in front of some cock cages. I was shocked at how many different kinds there were. Some looked medieval and majorly painful, others looked plastic and cheap, some even had keys to go with them.

They were more expensive than I'd imagined they'd be. For some reason I thought they'd be cheap: twenty or thirty bucks... and there were a couple in that range, but they looked so cheap.

Most of them were seventy-five to a hundred fifty dollars. I was continuing to browse the cages when I was startled by a woman asking, "May I help you with anything?"

"Um, yeah," I said, feeing like I was caught in the act. "I'm, uh, well, looking for something special for my girlfriend."

"A special occasion?" She asked, the woman older... in her forties.

"Four-month anniversary," I answered.

"I see," she said, not sounding overly impressed by that.

Then it occurred to me. I knew what I wanted. "I want a sex toy I can use on her while... um... I..." I said, then wasn't sure how to actually say it.

"While you go down on her?" she asked helpfully.

"Yes," I answered.

"You're a good man," she said, impressed I think, simply because I went down on my girl.

"She's the perfect woman," I replied.

"I know exactly what you need," she said. "Follow me."

She took me to a section with many uniquely shaped items... some of them obvious as to their uses and others that were enigmatic. The one she handed me was definitely an enigma. It was perfectly round and disc-shaped, except the thickness of the disc on one side of the circle was noticeably greater than the other. It also had an oblong hole in it... off-centre. The gadget looked quite elegant and seemed more for me than her... except the hole was way too big for my penis.

"I know, I know," she smiled, reading my mind. "It doesn't look like a vibrator at all."

"Is that what it is? No, it certainly doesn't," I agreed, as I studied the contraption resting in what looked like an oversized jewelry box. Definitely not cheap-looking. It was called a Lelo Ora 2.

"Yet it gives a woman the most amazing, slow build-up, long-lasting orgasms of any sex toy," she explained.

"How does it work?" I asked, curious how to use such a strange-looking device, it truthfully looked rather like a strange piece of geometric art you might see in a modern museum.

"You place the vibrating portion over her clitoris -- that's near the thickest part -- for the best effect, and the device has small rotating beads inside the circle that create sensations amazingly similar to a tongue," she explained.

"Sounds amazing," I said.

"It's the best of the best," she said, and then added with a sly smile, "and I'm speaking from personal experience. My Hitachi wand will give me almost instantaneous orgasms, but they don't last very long; my rabbit will get me off nicely if I want something inside me, but this jewel gives me the very best long-lasting orgasms. It's kind of like the difference between fast food and a seven-course banquet."

"But I don't want it to replace me," I said, thinking this sounded too good to be true.

"They thought of that; it can also be used to enhance the pleasure you're giving your lady," she explained and then added some more. "There are even ten different stimulations, for variety."

"Where do the batteries go?" I asked.

"You charge it on your computer."

"Oh."

"I can show you some less expensive options if you wish," she said. "We have many quality items to enhance your lady's pleasure," she offered.

"No, she deserves the best. I'll take it."

"You won't regret it," she said. "And she'll love it."

"I hope so," I said.

She took the box and said, "I know so. I've never had a customer come back not completely satisfied with this toy."

"Great," I said, dying to try it with Joan.

She rang it up and I didn't even react to its being way more expensive than I'd anticipated, over $250 after tax, but I didn't care. If it brought Joan the pleasure the woman promised it would, it would be more than worth it.

I picked up dinner on the way home at a small family restaurant I loved, ate, and was watching Wheel of Fortune when Joan arrived.

"What's this?" she asked, walking into the bedroom and finding the bag with her new sex toy in it.

"Shit, I should have put that away," I sighed, but I'd forgotten because I was starving when I got home... and I loved Wheel of Fortune, Vanna White being my lone nylon-wearing constant through the slow degradation of nylon fashion.

"It's obviously a sex toy, but is it for you or me?" she asked as she stepped in front of me, wearing a skirt and mocha-coloured nylons.

"Both of us," I answered, before adding with a smile, "although it's intended for your pleasure."

"Oh, cool," she said, as she pulled it out of the bag.

"Wait, that's for Friday; it's a surprise," I objected, but she wasn't listening.

"Too late," she said, as she saw the box and said in awe, "Oh, my."

"Do you know what it is?" I asked, "because I sure didn't."

"It's the Cadillac of sex toys for women," she said. "I almost bought one for myself a few months ago, but then I met my own Asian personal pussy pleaser."

"I wanted to get you something special for Friday, since you've already bought something special for me," I smiled, thinking of the strap-on, and flattered she preferred me over a toy.

"You're so sweet," she said, as she took it out of the box. "It's so pretty."

"It's like jewelry for your pussy," I joked.

She raised her skirt, revealing she was in thigh highs this time, and again no underwear, as she placed the toy right on her pussy. "How does it look on me?"

"Beautiful," I answered, admiring her ripe pussy.

"We need to test it out," she said, as she grabbed the charging cord and left the room.

I finished up my dinner, and was in the kitchen when I saw a bag on the kitchen table that she'd brought.

She returned and said, already googling it on her phone, "I wonder how long it takes to charge?"

"I didn't think to ask," I admitted, having planned to have it fully charged for Friday night. If she was going to make one of my fondest fantasies come true that night, I wanted to be able to return the favour in a meaningful way.

"Two hours," she sighed.

"Do you have anyplace to be tonight?" I asked.

"Not now," she said as she kept reading her phone. "It has ten stimulation modes and adjustable intensities, including one called ultra-intense."

"Cool," I said, unsure what else to say.

"It's even waterproof," she said.

I joked, "Since you take long baths."

"Now they'll be longer," she shrugged, then added, "plus, now I won't have to use the shower head."

"Fuck, you're hot," I said.

"So Erica, are you ready for plug two?" she inquired, shifting smoothly from one taboo subject to a different even more taboo subject, as I lagged behind, picturing her getting off with a shower head.

"I'm never not ready," I said, both excited to continue my anal training, the one still in my ass from yesterday doing nothing for me good or bad, but also nervous that a bigger one might hurt, and be more awkward to walk around or sit down with.

"Let's go to the bedroom," she said, grabbing the bag.

"You have the best ideas," I said.

Two minutes later I was on all fours on my bed, with my pantyhose pulled down to my knees as she pulled out the plug.

She placed it on a towel she'd brought, and then shocked me as I felt her tongue probing my asshole.

"Oh, that feels nice," I moaned, surprised at how relaxing it felt.

"Eating ass is something else you'll soon be doing," she said, as her tongue swirled around, and slightly inside, my back door.

"Really?" I asked.

"I didn't want you to think I was some cheap disposable slut, so I haven't told you all my kinks yet," she said as her tongue felt like it was reaching further inside my ass.

"Oh, you can tell me anything," I moaned.

"I love a good anal tongue licking, and enjoy a cock in my ass," she revealed.

"I'm gathering a very long list of the hot things you say," I said as she kept probing my asshole.

"And things I do," she added.

"Definitely," I said, her eating my ass now joining that second list. It wasn't stimulating me towards an orgasm, but it was definitely making my hard penis want some attention it wasn't allowed.

"You know, you really do have a man cunt back here," she said.

"I do?"

"I think so," she said as she sat up and then said, "Let's see if your cunt can take plug number two."

"Okay," I said, as she went to the bag.

I looked back and saw that this one was indeed larger in every way: length and girth, although it was only slightly longer than my flesh and blood version.

She lubed the toy, and then poured lube down my ass crack again, as I remained bent over, patiently waiting to be sodomized.

Sodomized... what a taboo term.

"In two nights, it will be my dick slamming into this cunt," she said, sounding so hot saying that, yet another sentence of hers to add to the list, as she moved behind me.

"That still seems an eternity away," I said, as I felt the cock at my hole.

"All good things come to those who wait," she said and then added, "and I stress the word 'cum'."

I was about to respond, telling her that same principle should also apply to the new toy I'd gotten her, but she pushed the cock inside me, and I let loose with a loud, embarrassing squeal.

It burned!

Not intense pain, no.

But a very clear protest from my asshole.

"Your cunt will need a bit of time to get used to being so full," she said.

"Okay," I said through gritted teeth, the pain increasing as she continued pushing, until the cock had entered me completely. I couldn't fathom how I could possibly fit the next one inside me, not to mention someone's BBC.

"Yeah, your cunt looks good, all full of dick," she said, as she seemed to be admiring me from behind.

"As do you," I said.

"Especially when it's BBC," she added.

"We both want the same thing," I joked, her admission she wanted black cock too, turning me on even as my ass burned.

"And we'll make it all happen," she promised. "I'm going to deal with a few emails. You should remain in that position as motionless as possible for a minute or two, and then slowly roll onto your back and rest like that for a few minutes... give yourself a chance to get accustomed to your new reality of having your pussy filled to bursting."

"Yes, Mistress," I said, smiling at her concept of my new reality.

She left the bedroom and I remained on all fours, trying to allow my ass, or rather my cunt, to get used to having something this big in it.

After a couple of minutes I slowly lowered myself to my side, and then rolled onto my back. I did it extremely slowly, settling my ass onto the soft bed so as not to push it deeper into me and create any new pain, since I was finally getting back to calmness. It still hurt, but the pain was diminishing noticeably.

Joan returned a couple of minutes later and asked, "How's is it going?"

"Could you have a look? I feel like I've accidentally gotten a dick stuck up my ass," I joked.

"Do you mean your cunt, Erica?" she corrected me.

"Yes, Sorry Mistress," I apologized. "It feels like I have a big dick in my cunt."

"It's not that big," she pointed out.

"It is for a pure sweet virgin such as myself," I said.

"Fair enough," she agreed. "But fret not, fair maiden, we'll soon get that sweet cunny trained to welcome a ten-inch BBC into its folds. Or do I mean its pucker? I do believe your tight little cunny has a pucker, how odd."

"I can't imagine accommodating the legendary Black Knight," I admitted frivolously, although while the idea was still a turn on, it was getting a lot scarier, now that it was coming closer to becoming a reality.

"I can already envision it," Joan smiled, as she leaned in and kissed me.

"Let's go watch a movie," she said. "My wonderful new Cadillac still won't be ready for over an hour."

"Help me up?" I asked.

"No, you've got to be able to do things on your own," she said, although she was kind enough to pull my pantyhose over my ass to keep the plug in place.

"That's not nice," I pouted.

"Hurry up," she said. "I need to distract myself from the toy I want to try so badly."

"Fine," I said, carefully inching myself to the edge of the bed. I managed to make it off the bed and onto my feet, but I yelped as the cock moved a bit further into my ass... I mean cunt.

"You should walk around a bit to get used to having it inside you."

"I can't fathom how anyone could ever get used to this," I complained, walking about as fast as a snail, every single step forcefully reminding me of the plug in my ass... each step creating a little jolt of pain but, I now began noticing, also a little pleasure.

"You may feel more pain and pleasure when you move," she said, "as it will likely stimulate your prostate."

"It's definitely doing that," I said, feeling my penis harden.

"Shit, everything turns your tiny penis on," she said, noticing it too.

"I'm easily stimulated," I moaned, as I kept walking, and noticed her shot at the size of my penis.

"I may have to pick up one of those cages for you," she said, as she took my hand and steadied me as she led me down the stairs to the living room.

"That may be a good idea," I agreed, both to eliminate the temptation to touch myself, and also to explore another of my fantasies.

"You actually want a cage, don't you?" she asked, stopping in the hallway just outside my living room.

"Maybe a little," I admitted.

"Or maybe a lot?" she pushed.

"Okay, maybe a lot," I agreed, loving how she saw through my silly façades to the real me.

"Good to know," she said and resumed walking into the living room.

I followed. On my own. I could do this!

I sat down extremely slowly, leaning heavily on the armrest, then as lightly as possible touched down, letting out a muted yelp as the cock reached new depths inside me.

Joan chuckled, but sympathetically. "Patience, my bitch."

"Yeah," I trembled, my pain being dulled by the natural thrills of obedience, and of fantasies coming true.

And for the next hour, we watched the first half of the new, surprisingly good, Yesterday. I'm a sucker for musicals... and although this wasn't a musical in the traditional sense, it was a lot of fun.

Joan got up and said, "My present should be ready by now."

"Go get it," I said, excited to see how it works.

"Already on my way," she said. "Meet you in the bedroom."

"But I want to see how this story ends," I said, in a whiney tone.

"And I want to twist and shout," she replied wickedly.

"So it's going to be a hard day's night," I joked, playing along with her witty Beatles title play.

"Now let's go upstairs and have some fun with a little help from my friends," Joan shot back, walking away.

I slowly got up, my ass actually feeling a little numb, and with a slight burn, as I followed her up to my bedroom. I needed to rely heavily on the railing and my upper body strength, but I made it... unassisted!

She was already on my bed, naked and with her legs spread, and the toy in her hand. "Good job, sweetie. Now get over here."

I got onto the bed, slowly, and crawled between her legs as she turned on the toy. "Oh, it's strong. And quiet."

"You're supposed to put this part right on your clit," I said, now close enough to dine on her delicious pussy.

"Okay," she said, and placed it directly onto her clit. "Oooooooh, my!"

"Good?"

"Very good," she moaned.

"Let me help," I said as I bent down a bit lower and licked her pussy.

"Oooooh," she moaned, "Okay, I have an idea."

She grabbed a pillow, lifted up her ass, slid it underneath and said, "There. Now you can eat my asshole."

"Okay," I said, not something I'd ever thought about doing, at least not until she'd eaten mine earlier tonight.

"Spread my cheeks and get to work, Erica," she ordered, as she placed the toy back on her clit and moaned.

"Yes, Mistress," I said, pulling her ass cheeks apart, extending my tongue, and licking her puckered back door.

"Oh, yes," she moaned. "Eat my asshole, baby."

I bathed her asshole, swirling my tongue around it... happy to discover it wasn't disgusting at all, just a little bit of sweet sweat.

"This toy is amazing," she moaned.

"Don't let it replace me," I joked, although that was my primary concern, so it wasn't much of a joke.