I left an absolute wreck. I only pulled on enough clothing so as not to arouse any suspicion should I encounter anyone on the way out of the building.

At home I took a quick shower, releasing myself from my cage to properly clean up. After that first sissygasm — even out of my cage — my cock didn’t even attempt to get hard. I locked it back up before leaving the bathroom and slipped into a pair of pink panties and a short satin nightie. I inserted my favorite buttplug — a five-inch “pink sugar” squishy one from Square Peg, just like the ones I knew to be Natalie Mars’ favorite. My ass was still sore from being hit with my belt, but wearing satin panties on the cool leather of my chair felt nice.

I posted a detailed accounting of the night’s activities — focusing on the feeling of being spit-roasted — with my first anal orgasm as the highlight. While I was waiting for Katie to post whatever video she had shot so I could reblog it I searched for the 150 Sissy Rules. I switched to the archive view and even then I had to jump backward by year and spent the better part of an hour before I found it.

Fifteen rules for sissies were on each of the ten pages. A sexy picture accompanied each set of rules, four of the ten pages were sissies with black cock which made me start leaking in my cage. As I worked to check off each of them, I noted the ones that I felt I had yet to achieve. Some of them, given my recent debut into sissy womanhood, would not be attainable for some time. Some of them, given my marital status, I was sure I would never be able to attain.

In the end, I calculated that I either had or was consciously doing sixty-five of them. Adding the sixteen that Katie assessed me as having attained gave me a total of eighty-one. Eight-one. Just sixty-nine to go.

Katie posted some of the video, which I knew to re-post on my page. It made my cock ache in my cage to see myself used at both ends. As always, I thanked Miss Katie for advancing my sissy training. She also posted the video of me cleaning up my sissygasm from the floor. She apologized to her followers for not filming the moment it happened but explained that she was busy spanking me for breaking a few important rules. My ass looked so red in the video!

Just as I was about to shut everything down and go to bed a private message popped up on my screen. It was Katie.

Did you let yourself out of your cage to wash?

Yes, Miss Katie.

And you locked yourself back up as soon as you were done?

Yes, Miss Katie.

Good sissy. All you need to bring tomorrow is a pair of white satin panties, a matching bra, your fake tits, and high heels.

Yes, Miss Katie.

I’m so excited about tomorrow! Get some sleep, sissy.

Yes, Miss Katie.

My morning routine included using my dildos successively in size order in the shower. I was still pretty tender after my spit-roasting, but I couldn’t resist recreating the event in my mind with a dildo on each side of the shower filling both my holes at the same time. I chose my large penis-shaped buttplug as I dressed for work. Without knowing what the night had in store — but having a good guess based on the last two nights — I wanted my sissy pussy ready for deep penetration.

I wore my white satin panties under my clothes. They were SKIMS brand panties in a full-coverage boy-short style. The legs were trimmed with a band of stretchy floral lace and they rode up snugly into my ass. The matching bra — a scoop-neck bralette — went into my bag along with the other items Katie had instructed me to bring.

I squirmed on my buttplug all day long — the constant feeling of a five-inch penis in my ass keeping me from even remotely concentrating on work. Around 3:00 I ducked into the bathroom and removed the Thin Tool. Adding a generous amount of lube, I replaced it with my Square Peg buttplug which, though “squishy,” was the same five inches only wider. I hoped this would prepare me for whatever was to come.

Katie came through right on schedule. She was still wearing the key to my cage around her neck.

“How are you doing today?” she asked brightly.

“My workout last night left me a little sore,” I said.

“Only a little?” She giggled.

“Well, okay, a lot.”

“I’ve heard the best medicine for that is really getting your blood flowing; you know, working a new set of muscles or working the same muscles differently. Maybe that will help.”

“Well, it’s certainly worth a try.”

“Yes, it certainly is,” she said in a lower register.

Like I usually did, I made my way to the men’s room after my co-workers all left the building. As I approached, I saw there was a sign on the door. “Out of order.” I wondered what kind of ploy this was on Katie’s part. Was she just trying to ensure privacy for whatever she had planned tonight?

I pushed on the door. Locked.

What was she playing at? Did she mean for me to go to a men’s room on another floor? Or did she mean for me to use the Ladies’ room?

I went to the opposite end of the hall. There was no sign on the Ladies’ room door. I knocked, somewhat hesitantly. Hearing no answer I pushed the door partially open and called out.

“Anyone in here?” I was answered with silence. I pushed the door all the way open and walked inside. This room looked much like the men’s room except there were a few extra stalls instead of wall urinals. There was also a bench on one wall — a sturdy padded bench upholstered in a medium gray faux leather.

I immediately knew that I had made the right choice. Folded neatly on the bench was a pile of bright pink. A short note on pale pink paper was on top of the pile.

Stacey,

Now that you have cum from being fucked like a girl

you have graduated to using the women’s room.

Unless otherwise specified, all of our future meetings will be here.

K

The pile of pink turned out to be a cheerleader costume. The skirt was pleated pink and black with bands of black and white trimmed elastic around the waist and along the hem. The top was a back-zip v-neck style crop top trimmed with the same black and white bands both around the neck as well as the criss-cross cut-out band under the bust. The word “SCORE” was in black-trimmed white letters across the bust-line.

I stripped quickly, putting on my bra that matched the panties Katie told me to wear. I added my fake tits and slipped into the top, which zipped up the back. I struggled with the zipper a bit but finally managed to get my top half together. The skirt had an elastic waist and pulled on easily, settling just right around my hips.

Above-the-knee athletic socks, also trimmed in black and white, completed my outfit. Under the whole pile was a pair of black pompoms. I stepped into my heels — black patent pumps with a 3-inch heel, and sat down to do my makeup. It was nice having a place to sit as I applied my face. My lips were painted with a creamy “poppy pink” from Tarte.

I wasn’t the least bit sure how she wanted to find me tonight, so I settled for the traditional cheerleader “start” position with my hands — clutching my pompoms — in fists on my hips. My chest was stuck out and my feet were a little better than shoulder-width apart. I held the pose for a minute or so before I heard a low rumbling noise.

The noise got louder as it approached, sounding more like heavy feet trotting down the tiled hallway. It stopped just outside the door, like whatever or whoever was coming stopped short.

The door opened and Katie stepped inside carrying a boutique-style paper bag. Uncharacteristically, she was wearing a hoodie instead of her usual t-shirt.

“You look delicious, Stacey,” she said. “We don’t have a lot of time so I’ll have to help you with this. Come here.”

I knelt on the floor where she indicated. She pulled two items from the bag. The first I recognized as a wig cap. She stretched it over my head, affixing it and adjusting it with expert ease. I didn’t have to guess what the next item out of the bag was.

The wig was a medium-length dirty blonde with layers and highlights. She settled the center-part wig on my head and quickly situated it so that my forehead was visible. She stepped back and indicated that she wanted me to stand.

What a difference the wig made!

I stared at myself in the mirror, hardly believing just how good I looked all made up and in a wig. I looked so amazing that I wanted to fuck myself! I felt my cock swell in my cage.

“Okay, Stacey. Are you ready for tonight’s fun?”

“Yes, Miss Katie,” I said as I resumed my cheerleader “ready” position in the middle of the floor.

“Cute,” she said with a smirk. She crooked her index finger and rapped three times on the door with her knuckle. The stamping of feet was renewed — not loud, just a low rumble of someone marching in place.

The door burst open and a stream of guys in football attire streamed in. They were not wearing helmets and I immediately noticed that there were five of them — four black guys and one white guy. They circled me and kept moving after the door closed behind them.

As the guys made laps around me, I noticed Katie out of the corner of my eye. She had wriggled out of her jeans and was grasping the hem of her hoodie. As she lifted the hoodie I could see she was wearing black crotchless panties. Her puffy pussy lips were quite prominent. She turned her back to me as the hoodie came off and my eyes were drawn to her ass. The crotchless panties had horizontal ruffles of white lace across the backside.

When she turned back she was wearing a deep v-neck bra-style top striped to appear like a referee’s shirt. It barely held her breasts and my trained eye saw that just a single snap in the middle under her bustline was all that was holding it together. It was short-sleeved and had a fake pocket outlined on the front. In addition to my chastity key around her neck, she also wore a black lanyard that had a silver whistle suspended from it.

She put the whistle to her lips and blew a loud tweet that made my ears ring in the confined space of the bathroom. The guys stopped running and turned inward facing me. Now that I could look closer at the football players it was clear that they weren’t wearing costumes — these were actual football players. Surely these were at least college players. High schoolers? My mind was spinning.

“Welcome to your cheer bang!” Katie said with an edge of excitement in her voice. I felt the gnawing of nerves in my stomach at the same time that I felt my cock swell in my cage.

“The rules are simple. Stacey here is our “head” cheerleader — get it? Head cheerleader? Anyway, she has two holes and two hands. That means there will be an odd man out. Whoever isn’t being handled by Stacey here can either eat my pussy or fuck Stacey’s tits.”

“Ooo-rah!” the guys all said in unison.

“We’re going to start with a little warm-up. Stacey, see if you can get these guys in the mood and see what you’re working with!” She blew the whistle again. I was stunned and didn’t have a clue what she expected me to do. Without any experience on this side of a set of pompoms, I was kind of at a loss.

I started to imitate some of the various cheer moves I had seen over the years — with the severe limitation of doing it in a pair of three-inch heels. I hopped up and down, shaking my pompoms and making my tits jiggle. I twirled around, making my skirt ride up. I moved my arms in classic “diagonal” and “bow-and-arrow” positions.

The guys started chanting, “Go-go-go-go.” I scooted backward, shaking my pompoms as I went until I backed up against the guy behind me. I rotated my hips, grinding against him. He gripped my hips and held on, grinding back. Katie’s whistle blew.

“Holding!” she said, laughing. He let me go and I moved to the next guy, working my ass on each of them in turn.

I made another lap, this time wrapping one leg around them and grinding on them like they were a stripper pole while my hand fondled their cocks through their poly blend pants. I made two more trips around the circle, which was slowly closing in on me. Soon I could grind my ass on one guy, tease the guy in front of me with my mouth, and rub the crotch of one guy on each side.

My antics were having the desired effect and soon I could see sizable bulges in four of the five pairs of pants. The white guy’s cock, though it was the first one to get hard, was only half the length of the other bulges. Katie blew her whistle again.

“Line!” she barked. The guys pulled away from me and formed a shoulder-to-shoulder line. Katie whistled again. “Head cheerleader, get to it!”

I didn’t need any more urging than that. I started with the first guy who just happened to be the white guy. I kneeled in front of him and fumbled with the nylon belt at his waist. It was a standard double D-ring belt that opened easily once I got it started. His pants were loose and dropped easily, giving me immediate access to his cock still encased in its white cotton athletic supporter. I tugged it to one side and slurped his cock into my mouth. Even hard it fit quite comfortably. I slurped on it for no more than a minute before the whistle blew.

“Switch,” Katie said. The next guy had already undone his belt and was ready for me. He dropped his pants and his cock was barely held in by his green strap. The word “GYM” in size XL was stitched on the wide waistband. I pulled it to one side, freeing his half-hard cock. I sucked on it greedily, feeling it growing in my throat as I worked it with my open mouth. We both groaned when the whistle blew.

Five minutes later, I had sucked each guy hard. When the final whistle blew I looked back down the line. I had four big black cocks — each one nine inches or larger, and one white one that was literally half the size of the smallest black one.

“Stacey, on the bench. Guys, you know the five positions. Let’s go! Let’s go!” The guys stripped quickly, revealing the well-muscled bodies beneath their practice jerseys.

I wasn’t sure just how this was going to work, but Katie’s earlier words at my desk about “working the same muscles differently” suddenly struck a chord with me. I sat down on the edge of the bench and laid on my back. I scooted down until my head was hanging off the end like I had seen in so many porn clips (and jacked off to) where throat-fucking was involved. I parted my legs wide and waited like an obedient little sissy slut.

The guys were huddled together, obviously trying to work out who was going where. Katie gave one last instruction.

“I’m going to start this cheer bang on my whistle. Every time I blow the whistle after that, rotate positions clockwise. Ready?” Her whistle tweeted.

The white guy immediately moved between my legs, tugging my white satin panties to one side. He pulled my sugar pink Egg toy from my ass and shoved his cock balls-deep inside of me. His little white dick barely registered with me after having had a five-inch toy in my ass all day. I didn’t have much time to think about my disappointment as I found a black cock in each of my outstretched hands. The largest of the black cocks was in front of my face and I opened my mouth wide to take it inside.

“Suck my fucking cock,” he said. He pressed it between my lips and as far down my throat as he could before I gagged. He stroked his cock in and out of my mouth as I tried to relax my throat. My hands each held a hefty piece of black meat.

With my legs in a “V,” the white guy was hammering away at my ass without even really drawing my attention. Suddenly he tensed up and started moaning. I felt him swell inside of me (maybe?) as he dumped his load.

“Aww, shit, Davey,” one of the black guys said. “You came already?” The black guys all laughed. Katie’s whistle blew.

I felt Davey being pulled away from between my legs. “Get over there and eat that pussy,” someone said. A pair of large rough hands moved between my thighs and I felt them brush my balls as they reached inside my panties through both leg holes.

“We ain’t gonna need these fucking panties in the way,” he said. He closed his hands in fists and pulled. The fabric gave way easily, ripping as he converted my full-coverage boy shorts into crotchless panties! My caged clitty sprung free.

“Sissy’s even locked in a pink cage.” He laughed.

“Shit, Willie,” the guy moving from my right hand to my mouth said. “You just gonna tear that shit up?”

“You know it, Dex,” he said. I felt his cock moving between my cheeks as he penetrated me. I moaned aloud, feeling every inch of Willie’s big black cock.

The big cock from my mouth, now in my left hand, felt even bigger as I stroked it. He said, “Awww shit. You hear that, Willie? She felt your black dick for sure!”

The new cock in my left hand chimed in, “Dex, you better plug that bitch’s mouth.”

Dex slid his cock into my waiting mouth and I had very little trouble taking him balls deep with his first thrust. His cock must be about nine inches I thought as I took it in both ends.

“Right down her throat to my balls,” Dex crowed. “One thrust!”

“Well, maybe when your dick's a little bigger she’ll be able to tell you’re even there,” the guy with the biggest cock said. The guy in my right hand snorted with laughter.

“Fuck you, Sampson,” Dex said, “ and fuck you too, Trevor!”

As I was fucked in both my mouth and ass, I stroked the other two black cocks in either hand. My mind whirled. With all of the banter, I was pretty sure that I now had all of the names of the participants. The biggest cock — the one currently in my left hand — belonged to Sampson. The next biggest cock — Willie’s — was in my ass. The other two cocks were roughly the same size but with very different shapes — Trevor was in my right hand and Dex was in my mouth. Davey, the owner of the little white dick, I presumed was eating Katie’s pussy.

With this vital piece of information, my brain felt free to relax enjoy the gang-bang Katie had set up for me. Willie was hammering away between my legs, spewing a steady torrent of sissy-related obscenities and slurs. Dex was using my throat to pleasure every inch of his cock, occasionally smothering me by lowering his balls to cover my nose while his cock was all the way inside of me. The guys in my hands kept me on task by gripping their cocks over my hands and using them to keep themselves hard.

I heard Katie moan as she was gripped with her first orgasm. As she came down from her climax she blew her whistle. As the guys rotated, I heard Dex groan. Apparently, he was pretty close to coming himself.

“You stay down there, pussy-boy,” Willie said to Davey. “We got this shit handled up here and it sounds like you’re doing just fine down there.”

I moaned as Sampson penetrated me. Before Trevor could get his cock in my mouth I managed to blurt out. “Fuck me, Sampson. Fuck me with that big black cock. Fuck my sissy pussy and make me cum like a girl!”

Trevor silenced me with a single thrust, but I continued to moan as Sampson’s bigger, thicker cock plowed my ass. After a few minutes, Sampson grabbed my legs at the knees and pushed them toward my head, changing the angle of his penetration. At this new angle, the swollen head of his fat cock brushed back and forth against my prostate as he continued fucking me. Clearly, he knew exactly what he was doing as each time he brushed by it he flexed his cock, making the head swell even more.

My orgasm came suddenly. I couldn’t cry out with a dick down my throat, but I moaned so urgently and loudly that Katie stepped closer, filming the whole thing. Sampson shortened his strokes, basically just poking at my prostate, massaging it with the wide head of his cock. My load spewed from the end of my pink cage and ran down over my balls to drip around where his cock was plugged into my ass.

“That’s it, sissy girl,” Sampson said. “Cum all over yourself. Give me some more lube for your bitch hole.”

“Aww, shit!” It was Trevor. “This bitch’s moaning is too much! I’m gonna come!” I sucked in as much air as I could before he smothered me. I felt his cock flexing in my throat.

“Holy shit!” Katie exclaimed. “I can actually see his cock in your throat and pulsing. Give her that cum, Trevor!”

Trevor finished his orgasm as I was coming down from my own. With a load already in my ass and the load down my throat fresh on my breath I was fast approaching the cum-drunk haze of my spit-roasting yesterday. I barely registered Katie blowing the whistle.

I missed Sampson’s big beautiful cock immediately as he moved to my right hand. As Dex stepped up, Katie moved her camera closer.

“Just look at the gape on this sissy’s pussy!” she exclaimed. “This girl needs more dick! Get in here!” Dex’s nine inches went inside of me with little resistance.

Willie timed his thrusts in my throat with Dex’s movements in and out of my sissy cunt. I was in a cock-slut stupor, being shoved back and forth between two beautiful black cocks. I was just a pair of open holes being used for a sissy’s ultimate purpose — pleasing cock.

I barely registered the guys moving again. I didn’t recall hearing a whistle. I think Willie jumped the line because the cock I felt invading me next was nearly as big as Sampson's. I think he was close to cumming in my mouth and wanted to shoot his load in my ass instead.

Almost as soon as he penetrated me his cock head swelled, pressing against my prostate. As he pumped his load inside of me I came again. My moaning was almost inaudible around Sampson’s cock in my mouth.

I don’t know if I actually blacked out, or if I just went into a deeper stupor. I felt pressure on my chest and realized Davey had climbed aboard. He was squeezing my tits together around his little white dick as he tit-fucked me. Sampson’s cock was in my pussy and Dex (I think) was in my mouth. I realized that someone was standing on the end of the bench near my head and that Davey had that person’s cock in his mouth now. How long had I been zoned out?

Sampson gripped my hips and shoved his cock all the way inside of me. I felt the heat and wetness of his orgasm as his cock spasmed deep in my bowels. The cock in my mouth was spurting as well, though not a huge load. Davey began moaning around the cock in his mouth as he shot his load on my face and between my tits. The cocks in my hands erupted as well, adding their jizz to the general mess.

Katie’s whistle blew three times — two short blasts and one long blast. The guys finished and stepped back, forming a quick line. Katie stepped forward and took a bunch of pictures. She made several lewd comments about how clapped out my pussy looked — gaped and leaking cum, how totally ruined my makeup was, and what a cum-covered slutty mess I was in general.

I dutifully crawled from the bench and took each of them in turn, sucking all five cocks clean. Dex, who was still quite hard having been blown by Davey when the whistle blew, came in my mouth one more time. Katie documented the whole thing with her phone. The guys departed one by one as I finished them. Soon it was just me and Katie left.

“I’m very proud of you, Stacey,” she said. “You’ve gone from a virgin sissy wannabe to a gang-bang slut in just four days! I can’t wait for this weekend! We’re going to have so much fun!” She clapped her hands excitedly.

“Thank you, Miss Katie,” I said. “Uhh, what do you mean “this weekend?”

“I wouldn’t want to spoil the surprise! Just be sure to update your blog and check your messages later.” I stood up and started to get undressed.

“Oh, no, Stacey. Tonight I want you to drive home just like you are — a real walk of shame for my gang-banged “head” cheerleader. I want you to send me a picture of you getting in your car and then one getting out when you get home.”

“Yes, Miss Katie.” I collected my things and made my way to the parking garage. I felt who-knows-how-many loads of cum running down my legs as I walked to my car. I snapped a picture of myself behind the wheel and sent it to her. I started the car and the clock read 7:45 pm — nearly three hours! How long had I been zoned out, I wondered.

As I arrived home I was grateful for the cover of darkness. I took one more picture and sent it as well. Katie’s reply only left me with more questions.

Good girl. Nothing tomorrow but crotchless pink panties, a matching bra, your tits, and your sluttiest heels. Nothing bigger than a medium buttplug — your pink jeweled one will be perfect!