"Sissified": 12 Days of Sissy-mas

I had to earn this load.

My throat was open, and my ability to breathe was sporadic, and I think I was taking all but the last inch, when he finally announced, "Get ready."

I was more than ready, and I kept sucking until he shot his load in my mouth. I milked his amazing cock for every drop of his cum... then continued just cleaning it up, not stopping until he eventually pulled out.

He said, "Thanks, man."

"No, thank you," I responded.

My jaw was sore and I waggled it around, figuring I was done. I was standing up to go when a voice ordered, "Over here, cock sucker."

I looked over and saw another flaccid black cock.

A smaller one.

I figured, Why not? One more for the road.

As I approached, the man surprised me by asking, "What's your name, sissy?"

No reason not to tell him, so I replied in my unmistakably masculine voice, "I'm Kendra, Sir."

"Well Kendra, it's nice to meet you. Will you please suck my cock?"

"Yes Sir, I'll be glad to," warming to his mix of humiliation and courtesy. I went over to it and took it into my mouth... getting it hard quickly.

"That's it, cock sucker," he encouraged me. "You're a natural, Kendra."

Once he was hard I bobbed hungrily, wanting both to deep throat this six-inch cock... same size as mine... and to get him off quickly.

After a couple minutes of deep throat sucking, he ordered, "Kendra, jerk me off. I want to shoot all over your slutty face."

"Yes, Sir," I agreed, a facial something that did intrigue me.

"Beg for my cum, Kendra-faggot," he ordered.

"Yes Sir, please come on me. Shoot your load all over my sissy face. Coat my face with your cum," I begged him, just as his cock exploded a massive load all over my face. The first rope hit me right in an open eye. A second rope followed, landing on my nose and cheek as I closed my eyes before two more ropes splattered my open mouth and chin.

"Thank you, Sir," I said. Between his courtesy and praise on the one hand, and his calling me humiliating names on the other, this man had kept my emotions swirling from warmth and gratitude, to the degradation I welcomed as a dirty slut.

"You're welcome, bitch," he said brusquely, before his cock disappeared.

My head still spinning from this chaotic treatment, I stood up and hurried out of the room before any more cocks showed up. I mean I kind of wanted more, but my jaw was sore, and my knees were aching. I briefly contemplated next time bringing along a cushion to kneel on, but that idea died a quick death when I pictured how it would look as I carried it in and out through the store.

I walked back into the store and saw Jeremy, a student in my Advanced English class, manning the till. I turned my face away and scurried out, praying he didn't recognize me.

Praying my wig and uncharacteristic outfit concealed my identity.

I got into my car and drove away, not looking at myself until I reached a red light.

My face was coated.

I looked like a cheap slut.

Fortunately however, completely unrecognizable.

I drove home, removing the wig when I got close. Happily, I didn't need to leave the car until I was in the garage with the door closed.

I went into the house and directly up to the washroom, where I saw my eye was red and bloodshot.

Fuck!

And I have to go out tonight!

I took another shower as I replayed the crazy four black cocks I'd sucked.

I felt dirty.

I felt guilty.

I felt hungry for more.

Fuck!

That night, I went to the party.

I drank.

I chatted with Paige on Facetime.

At midnight I didn't kiss anyone, but I did receive a text.

Your New Year's Resolution is to become a complete sissy. Say it.

I shook my head in... I don't know... Dismay? Self-loathing? Acceptance? Gratitude? Even exhilaration? I decided all of those terms applied as I whispered happily to myself, "My New Year's Resolution is to become a complete sissy."

DAY 8: Tuesday the 1^st

A New Year.

2019.

Day 8.

Last night I'd made a resolution that I hoped to keep.

A resolution I was scared to keep.

Paige would arrive home in a few days.

How was I going to explain any of this?

To Paige or to anyone?

That problem was for another day.

Today I was curious what would come next.

Today I was to go to my parents'.

Shit... in an hour.

I'd slept until one in the afternoon.

And I was still kind of hung over.

I went to the box and opened the Day 8 gift.

It was another butt plug.

This one had a pocket-sized remote control.

I read the note.

Kendra

Your training is getting close to the end.

Did you enjoy sucking cock yesterday?

Are you craving cock right now?

Are you craving cum right now?

Don't worry, we both know the answer.

Today, you will wear your new butt plug in your cunt from the moment you finish reading these instructions (unless you haven't yet showered) until you go to bed. You will, every hour, set the vibrations as follows:

Hour 1: 1 minute on level 1.

Hour 2: 2 minutes on level 1.

Hour 3: 3 minutes on level 2.

Hour 4: 4 minutes on level 2.

Hour 5: 5 minutes on level 3.

Hour 6: 6 minutes on level 3.

Hour 7: 7 minutes on level 4.

Hour 8: 8 minutes on level 4.

Hour 9: 9 minutes on level 5.

Hour 10: 10 minutes on level 6.

During the first nine hours you must experience the vibrations for exactly the number of minutes specified. The tenth hour, you may go longer if you wish.

But of course, you may not come.

PS: Each hour should start at the same minute.

Mistress M

This was going to be hard... pun intended.

I would be at my parents' for the next few hours.

Inwardly thanking my Mistress for her latitude I showered, dried myself off, lubed up the plug, and slowly slid it inside me. Even though it was longer than my other plugs, it was a little thinner than the dildo I'd used the other day, so I experienced only a slight burn.

I donned panties and pantyhose, jeans and a dress shirt.

I looked at the clock.

1: 25.

I started the stopwatch on my phone and turned the vibe plug to 1.

Ooooooh, my!

What a strange, pleasurable feeling!

No wonder girls love their vibes!

"Ooooooh!"

The minute passed far too quickly.

But when my phone dinged, I obeyed and shut it off.

I made the salad I always did for family dinners (I make an amazing Greek salad in case you care) and headed over.

I arrived at 2:20, 5 minutes before my next scheduled vibrating session.

I remained in my car for a few minutes, feeling compelled to obey the letter of the law... or I guess I mean of my instructions.

At 2:25 I turned on the remote and sat there enjoying the gentle buzz.

Fuck, I can't believe how nice this feels! My cock is getting hard in seconds!

Two minutes flew by, and I shut it off and headed inside... impressed with how naturally I was learning to walk with a toy in my cunt.

As usual, the next couple of hours were frantic.

People coming in.

Mom completing her preparations for the meal with help from her sister Mabel.

Dad watching football.

It was easy to sneak into the washroom at 3:25 and enjoy three minutes of vibrations, now with a pattern that briefly doubled in intensity every few seconds.

I was a minute late at 4:25 because I was out front helping grandma bring in the desserts from her car (her lefsa is the ultimate treat... I'm partly Norwegian in case you care). I hurried back outside once I'd set down my first load of dessert trays, so I could do my four minutes. This session seemed super long, because I was outside and people were waiting inside... and just as the fourth minute began, a car pulled up.

I allowed the pleasure to continue as my auntie and uncle got out of their car. My uncle Harold was old school, so my Aunt Rosemary waited patiently while he walked around the car to open the door and assist her in rising. Such a gracious couple!

I waved to them using that as an excuse to delay before grabbing the final tray from grandma's car, with ten seconds left.

I lingered for the last pleasurable seconds before reaching in my pocket to shut it off just as Aunt Rosemary called out, "Happy New Year, Kenny."

"You too, auntie," I replied, as I walked into the house with my pussy simmering down, but my hard-on wanting more.

I'd just finished dinner when hour five came around.

I excused myself to the bathroom again, and discovered level three was faster, and it featured three quick, intense vibrations every few seconds. Most bathrooms can be embarrassingly effective sound chambers, but fortunately my... my cunt plug?... was quite silent.

At 6:25 as we watched television and sat on couches and easy chairs while eating dessert, I decided to turn on my plug while I was in a room with other people. I was sitting in a chair by myself, and the television was loud, because my father has hearing problems.

I'm not going to lie: it was exhilarating to enjoy six minutes of secretive pleasurable vibrations while we all watched TV. I even answered a question more or less intelligibly while I indulged myself.

I was in the kitchen, my pussy still feeling the after pleasure of the six minutes when Mom asked, once we were alone, "Are you wearing pantyhose, Ken?"

I froze.

"I can see the top of them," she explained.

"Oh," was all I could say.

Mom added, as she tucked the back of my shirt in for me, "It's no big deal, sweetie. I love wearing them, too."

I turned around and told her defensively, "I don't normally wear them."

"I'm happy whether you do or don't. No judging," she shrugged and then added, "I mean, you used to wear mine all the time."

"You knew?" I gasped.

"You used to leave some interesting stains in my panties and pantyhose," she smiled, just as Aunt Rosemary walked in.

"What are you two talking about?" she asked.

"The past," Mom answered smoothly.

I was mortified, but also relieved that Mom knew I used not only to use, but even to ejaculate in her panties and pantyhose, and she seemed okay with it. If she could keep my secret for this many years, I had no worries about her opinion of me and her discretion at this late date.

I wished our conversation could have gone further, but we were never alone again for the rest of the night.

At 7:25 I did seven minutes on level four. This one gave me a wide variety of fast and then slow vibrations... never predictable... creating a variety of pleasures. Fuck, each hour enhanced the pleasure. And God, did I want to come.

I headed out at precisely 8:20, giving myself enough time to drive to a 7-11. I turned on the vibrations for eight minutes in the parking lot. God, I needed to get fucked! I wish I had permission to fuck myself with that dildo again.

Maybe I could?

No, bad idea: it was okay to fuck myself, but not to come. That would be too frustrating.

Although I was supposed to continue on with this vibrating pleasure stick for ten straight hours.

I'm not sure my ass (my pussy) would ever be the same after the dildo before and now the amazing teasing pleasure of my vibrating plug.

After my eight minutes, I went into the 7-11 and got a slurpee, not worrying about the caffeine, figuring I needed to remain awake for two more hours at least.

I got home, got undressed, just remaining in my panties and pantyhose, and logged online.

I was scrolling through Tumblr browsing through sissy gifs for a few minutes before I spied a link for hypno sissy videos.

I'd seen that before, but had never clicked on it.

Figuring why not, I clicked on it.

I then spent more than two hours immersed in a whole new world. A world that seemed like a natural extension of the past eight days.

I watched a few videos:

-girls sucking cocks, while I could hear soft but still audible words repeated over and over: "You're a cock sucker."

-girls sucking black cocks (scenes changing every few seconds) as a different and sultry voice called me (well, whomever was watching) a variety of names belittling my manhood compared to superior BBC.

-shemales getting fucked (shemales are damn hot) by a variety of cocks.

-white girls getting ass fucked in rapid succession by BBC (following each five-second scene, a word flashed on the screen: faggot, cock sucker, bimbo, slut, etc.)

-girls bouncing forward and back, taking two cocks at once (the sultry voice was back, this time periodically purring different phrases: "Your cunt loves cock... Your tummy loves cum... Dirty sissies are good sissies... Girl cunts produce beautiful babies, but sissy cunts produce only something too filthy to mention..." and on and on.

As I continued watching these vids, I did hour nine. The vibrations were now more intense and more varied. I was never fucking hornier in my life!

Then as hour ten hit, I turned on level six and could do nothing but moan, it was so intense. Fast hard vibrations that literally had my body trembling.

I watched another captivating hypno sissy video that focused on BBC.

Then Paige called.

Fuck! I still had five minutes left in my ten-minute minimum.

"Hi, honey," I greeted, after putting the laptop on mute.

"Miss me?" she asked.

"You're gone?" I asked with my usual sarcastic wit.

"Asshole," she teased.

And it's really full at the moment, I thought to myself as it vibrated like crazy. "I miss you too."

"Only a few more days," she said.

"It's been forever," I said.

"Yeah, I mean, I haven't seen you since last year," she joked, something I would usually say.

"That's my joke," I protested.

"Clearly we've been dating too long," she teased. "You've corrupted my wit."

"An eternity," I said.

"So... what have you been up to?"

"Watching a lot of porn," I admitted truthfully.

"I bet."

"You?" I asked.

"Sightseeing every day," she said, before adding, "I've finally concluded you can see too many castles."

"I bet," I said, trying to pay attention to the love of my life while I watched big black cocks destroying white girls' asses.

"You seem distracted," she observed.

"Just tired," I lied, "doing New Year's Day with the family was great, but I was there for hours." I was feeling good about my dissimilation until I let out a soft moan as the toy soared into an intense vibration pattern.

"Did you just moan?"

"No, but I did just yawn," I said.

"Bullshit. You're watching porn," she caught on.

"I plead the Fifth," I admitted.

"I'm stuck in a hotel room with my Mom, and you get to watch porn," she sighed, the only girl I'd ever dated that liked watching porn. When we watched it together, it often led to some great sex.

"Yep."

"I'm hiding out in the bathroom, so for now I can say whatever I want. What kind of porn are you watching?" she asked.

"BBC porn," I admitted, skirting the hypno sissy part.

"I do enjoy the feel of a nice big black cock," she teased, reminding me of her last boyfriend.

I thought to myself, Me too, but only said, "I know, I know."

"Anal?" she asked.

"Yes, please," I joked.

"The scene, asshole."

"Of course it is," I revealed.

"You and your fascination with anal sex," she said.

"Hey, blame Deadpool," I protested.

"You know I still have my strap-on from my college days," she revealed.

"You do, do you?" I leered with my voice. She had been rather frank about her college days which besides her black boyfriend, had included a few lesbian encounters.

"I figured maybe we could have a threesome one day," she continued driving me crazy.

"I love you," I said.

"You know, I think I'll buy us a new strap-on," she said. "I mean we'll be in Amsterdam tomorrow. Where better to find a sex toy?"

"Make sure it's big and black," I joked, although I wasn't really joking at all.

"You keep talking like that, and I'm going to come home and fuck the living shit out of you," she said sexily.

"Don't promise anything you can't back up," I said, hinting I was okay with it... which I was.

"Trust me," she continued. "When I put on a cock, I become a different person."

"That I want to see," I said, imagining her pegging me.

"Clearly we both need to get laid," she appraised.

"Agreed," I said.

"I need to get in there," I overheard her Mom saying.

"I was about to suggest some phone sex, but alas, I have to go," she sighed.

"I'll just go and use a vibe in my ass then," I said. I really said that? That was way too honest!

"You better not," she forbade me, before adding, "that ass is mine."

"Mmmmmm," I mmmed noncommittally.

"Although unfortunately we won't be arriving back until Sunday the sixth, instead of this Saturday like we'd planned. So... you and I will have to put off any ass-claiming until then."

"That is a shame: I really miss you," I replied. I realized that her delay also meant that I'd now complete my 12-day training the day before she got home.

"I miss you too. Love you," she said.

"Love you too," I returned.

I hung up, turned up the volume and watched the rest of the scene.

I then sighed... knowing I wasn't allowed to come... so I shut off the laptop and the toy.

I went into the bathroom to take out the plug and clean it, suddenly feeling empty as I got ready for bed, replaying that Mom knew about my hosiery wearing perversion.

Weird.

DAY 9: Wednesday the 2^nd

Two-thirds done.

Only four days left.

What could be left?

Only one way to find out.

I went downstairs and opened Box 9.

This one was also empty except for a note.

I read the note.

Cock Sucking Kendra

On your phone, in your apps, is an app called SCORE. Your account is already created with the username SISSYCUMBUCKET and your password is BIMBOBITCH.

You will need to answer the questions yourself, but once you finish, you can get all the cock you want.

You must take at least three loads today, but if you want, you can take as many more as you wish.

PS: If you feel ambitious and are craving some BBC, go to the top floor of the engineering building at the college and you may never leave.

PPS: You may suck as many cocks as you wish: 3, 5, 50, but you may not take anything up your cunt.

Mistress M

Of course, the first thing I did was find the app and log in... not really concerned how it got on my phone in the first place.

Questions popped up.

Yes __X__ No _____ 1. Do you suck cock?
A few days ago the answer would have been no... but now it was a definite YES!

Yes __X__ No _____ 2. Do you swallow?
Again... a recent YES, and the question had me craving another load in my mouth.

Yes _____ No __X__ 3. Are you a bottom?
I hadn't done that yet... but I had come from a vibrating dildo in my ass, and was curious. That said, I answered with my truth of the moment.

Yes __X__ No _____ 4. Are you submissive?
Based on the first eight days, that had to be a big YES!

Yes _____ No __X__ 5. Do you want to top?
I wanted to suck cock.

I maybe wanted to be fucked.