Sissification 101: Ch. 03

Sissification 101 Ch 03

Summary: Eric(a) gets pegged for the first time.

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.

6. PEGGED... A LOVE STORY

FRIDAY

Joan was already gone when I woke up; she was a morning person.

She left a note:

I want you in the white panties and the complete set of white lingerie all day, and of course the cage, since I have the key.

Looking forward to tonight.

Love Joan

The only thing I focused on as I read the letter was one word: love.

She loved me.

After a few of the craziest days of my life, each more amazing than the previous, I was getting ready for an even more amazing one: both romantically and intimately.

Today already hadn't gone as originally planned, as I'd told her I loved her last night, instead of waiting. That said, everything else was in line for the night of our lives.

I took the plug out.

I got out of bed.

Standing up, having been lying in bed the entire time I'd been in the cage, I realized how heavy it was.

It seemed, ever so slightly, to pull my clitty down.

I looked at myself in the mirror with my clitty caged.

It looked so pathetic and fragile.

I showered, which was a little awkward with the cage, especially while trying to wash my clitty.

I put on the lingerie... that challenge taking way longer than I'd anticipated. The garter-belt was difficult to figure out, and I didn't realize until I went pee that I should have put the panties on after the garter-belt and stockings, not before. Unfortunately I didn't have time to fix it, as I was already running late. Which made getting my clitty out to pee, even more of a struggle.

I went to work, and it was the longest day ever.

First, all I could think about was Joan, and the night ahead.

Second, every second Friday Joan's entire department had the day off, so she wasn't even there.

Third, I couldn't focus on anything, as I imagined Joan wearing a strap-on, or Joan taking Carter's BBC in one of her holes (I could just tell he had a big cock).

Fourth, Joan teased me all day.

A morning text: Just a picture of her strap-on and some lube lying on her bed. My clitty desperately tried to get excited, but thwarted by the brass ceiling.

I texted back: Who is that for?

But she didn't respond to my playful banter.

At 10:00: A picture of just her feet, her toenails freshly painted ruby red, in black nylons. My clitty desperately wanted to salute the beautiful, perfectly manicured toenails, but the cage said, Nope!

I texted back: Those look perfect. I can't wait to worship them as they deserve to be worshipped.

At 11:00: A picture taken by someone else, of her at a salon getting her hair done.

I texted back: You look amazing, honey.

At noon: A picture of a gloryhole with the caption, Don't you wish you were here?

My clitty so badly tried to answer that one with some action, but was denied entry, a constant reminder that 'you know who' was in charge of it.

I texted back: I hope we go on a date there someday soon. We could both gobble up all the chocolate we could handle.

Every single time, she was ignoring my responses, or at least not replying to them, which was frustrating. And because of my chronic insecurity, a little rattling... even though if I stepped back for some detachment, it seemed pretty obvious I had very little, if anything at all, to worry about.

At 1:00: A picture of a white woman between a black woman's legs. It wasn't Joan, but her question was hot... How badly do you want to see me eating a chocolate cunt?

I responded: My clitty tries to destroy the cage when you ask a question like that.

No response from her.

At 2:00: A picture of a black cock... a big hard black cock. Just visiting Master Carter. Don't worry, I didn't do anything other than watch him stroke and get hard so I could take the picture.

Oh fuck.

Carter's dick was huge!

Easily 10 inches.

Thick.

Majestic.

Captivating.

Mouth watering.

Cage rattling.

I had nothing against her sucking or fucking him... although if I had a choice, I'd want to be on hand to watch.

I responded: Please tell Master Carter his cock is mouth watering, clitty crowding in the cage, and amazing.

At 2:10: An open mouth displaying a big lake of white cum in it. I promise I didn't touch his big black cock, although I wanted to so badly. I didn't suck it, or let him fuck me, although I promised he'd be our first if we decided to follow through with serving a BBC Master for the two of us. That said, he insisted I catch his big load, and savour it for you. I obeyed, as a good submissive will do for ANY BBC.

God, I needed out of this cage.

If I had the key, it would be unlocked and I'd be spewing my load in seconds, I imagine.

Yet I didn't have the key.

I was completely helpless, and at the whimsical mercy of my beautiful girlfriend.

I texted back: You're a very lucky BBC cum slut... which I hope I get to join you in being VERY, VERY, SOON. PS: my clitty has a headache from her day of desperate attempts to salute every picture and message you've sent me.

Still no response from her... it was amazing how needy I was becoming. I needed her validation. I needed her voice. God, this was definitely love.

At 4:00: A gif of a guy getting spit-roasted. A BBC in his mouth, and a strap-on wielded by a hot blonde at his back end. The message this time had me aching in ways I'd never felt before: Carter and I discussed trying this position with OUR sissy.

Our sissy.

Holy fuck.

That should have terrified me.

I'd willingly given myself mind, body, soul and caged clitty to the woman I loved... and it seemed that with that willing submission I was also surrendering all my freedom, plus any vague semblance of normalcy (if that even existed anymore) to a black college stud.

Each text made my clitty ache with frustration.

And with discomfort.

And acceptance.

I replied, making it clear I was ready to replace that guy: My mouth and pussy exist only for my Master's and my Mistress's pleasure.

I pressed Send, feeling a rush of adrenaline course through me, as my clitty struggled against her restraints uncontrollably, like a desperate fish on a hook.

For the first time she texted back, just a single word: Soon.

And at 4:30: Go to your office... NOW.

I was actually just shooting the shit with Kevin, a partner, when the text arrived.

"I've got to get going," I said. Kevin knew, and even cared, that today was our four-month anniversary, as he was a romantic guy who still brought flowers home to his wife... weekly.

"Joan?" he asked.

"Yep," I nodded.

"Enjoy tonight then," he said, completely unaware of the new power dynamic that had surged into place for us this week.

"I imagine it's going to be life altering," I said, thinking of that strap-on.

"Don't go in there demanding too much of yourself," he cautioned. "Just be who you are."

"For the first time in my life, who I really am is exactly who I'm being," I said, feeling so liberated not to be living a lie anymore. Well, I was definitely living a lie to Kevin and everyone else who knew me... but with the one I cared about the most, I was completely naked in every conceivable way... although physically naked only when it was allowed.

"That's great," he said, and then joked, "Don't do anything I wouldn't do."

"I'll try," I smiled, as I headed to my office, wondering if Joan was there, and thinking it unlikely that Kevin ever got pegged.

To my surprise, she wasn't.

But there was a giftwrapped box on my desk.

Having no idea what it was, just knowing I'd be better off if no one saw my gift. I closed and locked my office door, then unwrapped the box. According to the outside, it was called a Dual Vibrating Egg for Penis and Anal Vibrating sex toy.

My phone rang.

It was Joan.

"Hi, honey," I greeted, looking forward just to hearing her voice.

"Hey, baby," Joan replied. Just those two words, and my heart melted. "How was your day?"

"Nowhere near as exciting as yours.''

"Everything I did today was for you, baby."

"Everything?" I teased, slightly scoffing.

"Well, I did receive some benefits from doing them, for sure," she admitted cheerfully.

"Was the chocolate satisfying?"

"I'm sorry to say that I was just allowed to have the creamy filling," she said. "Although I was really tempted to gobble down that chocolate whole."

"I can imagine," I said, visualizing my beautiful girlfriend on her knees sucking that young big black cock.

"You're imagining me sucking Carter's big black cock, aren't you?" she nailed me.

"I plead the Fifth," I responded with a slight chuckle, in awe of how well she knew me.

"I'll take that as a 'yes you most certainly would like to see me with ten inches of Carter's big thick black cock in my mouth'," she said wickedly.

I responded, countering her nasty words with some of my own, although I whispered them, somehow nervous to be heard outside my office, even though I knew that would be impossible, "Or seeing that big fat youthful cock slamming into that pink pussy of yours."

She jumped right back with, "Or even rooting up my tight asshole."

I countered, each of us upping the other's sexual ante, "Or tearing apart my virgin cunt."

"Okay, you win," she laughed, before adding, "although that virgin cunt is mine."

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

"On that happy note, what do you think of your gift?" she asked.

"It looks, umm... confusing," I said. Basically it was a couple of bright-coloured smallish objects connected to each other with electrical wiring; and that was it. "Umm... I'm guessing the one shaped like an egg should go in my ass."

"That's right, and I expect it to go in your ass right now," she said. "I left some lube in your top left-hand desk drawer."

"Okay, but what about the other one?" I asked.

"It's a clamp, and usually it would go around a cock," she said, "but you don't have one of those."

That hurt, yet turned me on.

"It could also go around your clitty, except for that tiny thing being caged," she added, humiliation compounding humiliation... which only added to my complete sexual submission. "See if it can fit around your cage."

"Okay," I said.

"Do it now," she ordered.

"Okay," I repeated.

"Okay, what?" she snapped.

"Okay, Mistress," I corrected.

"Good girl," she said. "First of all, see if the clamp fits around your cage. When I bought it on Monday evening, I hadn't even thought of caging you yet."

"Okay, Mistress," I said, taking my pants down.

I grabbed the toy, awkwardly worked it inside my panties (I really should have put the panties on outside the garter; it had been a complete inconvenience this way all day). Although not a great fit, it did fit around the cage, just awkwardly.

"It kind of fits, Mistress," I reported.

"Good. Now lube up the egg and slide it in your pussy," she ordered.

"Okay, Mistress," I replied, getting more excited with each order she gave me.

"You love being told what to do, don't you?" she asked, as I opened my desk drawer and saw the lube immediately. She likely should have put that somewhere a little more discreet, but it wasn't for me to criticize.

I admitted, "It's like you can read my mind."

"Well, we're both very similar kinds of sexual deviants," she said. "We have lots of the same kinks."

"Well, there is that," I laughed, as I coated the smallish egg with lube. This would be a lot easier to slide into my pussy than the last plug, and also assumedly easier to walk around with.

"You like being my slut?" she asked.

"I love it," I admitted, as I stood up, positioning myself to slide the egg inside my needy cunt.

"I know you do, my slutty, sissy pet," she said wickedly.

"Oooooh," I moaned softly as the egg slipped inside my pussy.

"I heard that. Is it in?"

"It is," I answered. I then added, "Umm... but according to the packaging, there should be a remote."

"Should there?" she asked with such blithe innocence that I knew she'd taken possession of it.

"I can't wait to see you," I said, having been looking forward to this special night even before it had become a sexual special night.

"I can't wait to see you too," she said rather sweetly. I was anticipating more of a disparaging response, so her tender answer made me smile. I hoped this was more how she truly felt, and her endless putdowns were just playing the game to make me happy in the twisted fashion I needed.

"Six o'clock," I said.

"Don't be late," she said.

"You're the one who's usually late," I pointed out, me always striving to be at least ten minutes early for any appointment.

"Yeah, yeah," she said. "I've got to go, Got to finish getting ready."

"Love you," I said, the words flowing off my tongue so smoothly.

"Love you too," she replied, and hung up.

It was crazy how we could segue from two completely opposite modes in a moment: from dominant Mistress vs. submissive sissy sub, to two lovers uttering sweet, tender, declarations of love to each other.

I pulled up my pants and sat down, my pussy so well trained by now it easily swallowed the egg whole, giving me no discomfort at all. And the padlock on the cage wasn't noticeable at all, my having rotated it beneath my scrotum so as not to give me a bigger looking package.

I finished work. Well, really I played five games of Clash Royale, before I left the office to head out for the night of my life.

But first I went home.

Changed clothes... well, not all my clothes, the lingerie remained, but I did at long last undo my stocking clasps, take my panties off (weird saying my panties), re-clasp the stockings, and put the panties back on where they should have been in the first place. There was a lot to learn about being a girl.

That felt way better.

I grabbed the bracelet.

I drove to the restaurant and arrived twenty minutes early.

Joan, as usual, arrived ten minutes late. I was already seated, and had wine poured for both of us.

I didn't see her arrive... I felt it.

Buzzing started in my pussy.

Intense buzzing, with wild sporadic patterns and vibrations! Whoo!

I had to grab the table to steady myself, as the toy stimulated my prostate perfectly, and my clitty also tingled with mind-numbing pleasure, while the vibrations also rattled my cage (and thus my clitty, and fortunately not very loudly).

A moment later Joan arrived where I could see and greet her, and like the gentleman I was, I stood up for her. She smiled and said, "You look handsome."

"You look amazing," I returned, admiring her red dress, black stockings (I assumed they were stockings on an occasion like this), and five-inch red heels.

"Don't I always?" She asked, as she leaned in and kissed me, her hand reaching around to my ass.

"Always," I agreed, as she squeezed my ass.

"You're literally vibrating with excitement," she playfully punned (which, to my surprise, is an actual word).

"I've been thinking about you all day," I said.

"I've been thinking about you all day too," she replied as she sat down... as did I. Although very cautiously, as the buzzing continued at an intensely pleasurable pace.

"Well, now we're here," I smiled.

"Yes, we are," she smiled, as she took a sip of her wine, and a moment later the vibrations shut off. She said, "I probably shouldn't have made my entrance so... shall I say, titillating. Because the rule tonight is no sex talk during dinner."

"Agreed," I smiled, as our waitress came by, and we ordered a couple of appetizers and our entrees.

I won't bore you with details of the next hour, but we chatted about where we should travel this summer (she wanted to go to Italy... it's her dream trip, although she wants to hit all of Europe whenever time and money will allow), we discussed why most of the best music was in the 1980s or earlier (including that back then everyone wrote their own music, and could actually play an instrument (auto tune should be illegal)), we agreed that the best movies were action movies with some humour, and we pondered when we should introduce each other to our families (concluding, albeit with a little trepidation, her parent's 40th wedding anniversary in three weeks would be the best time).

I thought this would be a good moment to pull out the jewelry box and place it on the table in front of her. "Just a little something for the woman I love."

"You shouldn't have," she said, taking the box.

"Yes, I should have."

"All right, yes, you should have," she laughed as she opened the box. "Oh, it's beautiful!"

"I hoped you'd like it," I said, having spent a long time looking through a variety of bracelets before choosing this one.

"I love it," she said, her smile and red cheeks confirming she really did. "It's so sweet."

"And I love you," I smiled, loving those three simple, yet all-empowering words.

"I love you too."

The waitress arrived, and we ordered a cheesecake to share.

"So, this play may be a little too much for you," she cautioned.

"How so?" I asked. I love musicals, which stereotypically may explain my sexuality crisis. Yet I wasn't gay. I loved Joan, and she turned me on both before and after she caught me in the act, per se. However, I was beginning to accept I may be bisexual. Or more of a natural cuckold, if that's a thing. Who knows? Labels are always annoying, as they try to pigeonhole everyone too restrictively.

"There are a lot of black men in this play," she smiled.

I laughed as I countered, "Then It could be too much for you, as well."

"Touché! So it should get us both all revved up."

"With someplace to go," I sang, playing on the Meatloaf song and our plans for after the musical.

"Indeed," she smiled, as the cheesecake arrived, and the buzzing in my clitty and pussy resumed, this time at a lower setting.

"Nice," I said, controlling a moan, as the waitress assumed I meant the cheesecake.

"Enjoy," the pretty girl said.

"Oh, he will," Joan spoke for me.

She walked away looking a little perplexed, just as a shoeless foot reached between my legs.

"Horny?" she asked, as I reached down to grasp the sheer, silky foot.

"Pretty much twenty-four seven," I replied.

"The cage is working, then," she deduced.

"It seems to be," I nodded. "It keeps me in an almost perpetual state of frustrated arousal, which I guess is the point."

"Hey, that was me when I was still single," she joked.

"And that's also every guy around," I replied, as she put pressure on my crotch. "Ever."

"Touché again," she smiled, as she reached out her fork for another bite of our cheesecake.