I appraised my disheveled appearance in the bathroom mirror. My skirt and cheer top were a cum-stained mess and the cum all over my face and neck had dried to a crusty layer. I had no idea how to care for the wig on my head that was also matted with cum, but I had a feeling I was about to learn. I still had no recollection of well over an hour’s worth of my time that night, so I was hopeful that Katie’s videos might shed some light when she posted them later.
I wrote out my account of what I remembered about my “cheer-bang” — focusing mainly on what it felt like to handle four big black cocks at the same time. I made mention of how my panties were ruined by Willie tearing them open but forgave it because I should have made sure my sissy pussy was accessible for him. I posted it to my blog and then went to shower.
Showered, locked back in my cage, and dressed for bed (in pink of course) I sat down to check for Katie’s posts. While I waited for her to post her point-of-view for the night’s activities I researched wig care videos. I watched quite a few before I felt I had a handle on things. I found some appropriate detergent and gave the wig a good wash, followed by a thorough rinse. I was a little stymied about what to use as a wig stand, but I McGyver’d a solution that I felt would work as a substitute.
I returned to my blog and found that Katie had posted a lot of the video. After re-blogging them all, I watched every last minute of what she had posted. I now knew why I had been such a mess! Throughout the nearly three-hour encounter, each of the five guys had cum in or on me in some capacity at least twice each and I had had a cock in both holes nearly the entire time! I could tell the moment my mind shut down and my body went on “auto-pilot,” and the exact moment I “came to” with Davey tit-fucking me. I had zoned out for just over an hour during which I was still actively participating.
Katie, seeing me online, popped into my PM feed.
Hey, my little gang-bang slut! How are you feeling?
Good, Miss Katie. Sore, but good.
You were an insatiable animal tonight! I can’t believe you came three times from being fucked! Have you watched all the videos?
Yes, thank you, Miss Katie.
Sorry about your ripped panties! Sometimes that happens to us girls when the guys get excited.
I understand, Miss Katie. It was my fault.
Be sure to add stockings to the list I gave you.
Yes, Miss Katie.
How bad off is the wig? I know you took more than two or three loads to the face.
I washed it and it is drying now, Miss Katie.
Such a good sissy! Bring it along, too. Get some sleep! Tomorrow is all about fun!
Yes, Miss Katie.
I went to bed wondering if I should have mentioned how I completely zoned out to her. Sleep did not elude me, and I woke to the gentle buzzing of my alarm.
I dressed for work with my crotchless panties under my male underwear. I figured this way I could keep the panties fresh and let all of my dribbles soak into my boring white cotton Y-fronts.
The satin front of the panties had an inverted triangle of lace and the front opening was trimmed with a narrow line of scalloped lace. Unlike some crotchless panties, these were really open and my caged clittie was easily sticking out on full display. The back was entirely made of lace and the rear opening — trimmed in the same scalloped lace — gave easy access to my sissy pussy as well. A decorative keyhole detail was above the rear opening.
I packed a small bag with a pair of white patent leather pumps with four-inch heels and a sexy ankle strap, a matching pink bra, white seamed stay-up stockings, my tits, my medium metal buttplug with the pink jewel, and the wig.
I was actually able to concentrate and get some work done — so much so that Katie caught me unawares when she came through on her rounds. She always came earlier on Fridays and today was no exception. We maintained our very public idle chit-chat.
“Hey there,” she said, cheery as ever. She was still wearing my key around her neck.
“Hey, you doing okay?”
“I am. Looking forward to tonight.” She paused, piercing me with her gaze. “Girl’s nights out, yo! Whoop whoop!” She raised her arms in a “raise the roof” style gesture.
I was speechless. She spoke in a low voice.
“What’s the matter, black cock got your tongue?” She raised her voice to normal.
“Yep, just me and my girlfriend hitting some clubs and getting hit on!”
“Umm, well have a good weekend,” I managed. She lowered her voice again.
“Oh, we will, sissy. We will.”
The rest of the day sped past. I was distracted and could not even imagine what plans she had for me. Now that I had “graduated” to the Ladies’ room I couldn’t go get prepped early anymore. As 5:00 pm approached people ducked out early, leaving me completely alone. I made my way to the bathroom, knocking on the door.
“Anyone in there?” I asked. Hearing no response I entered and sat my bag down on the vanity. As I started pulling my stuff out I heard a toilet flush in one of the stalls. I froze, mortified, dropping one of my heels in my shock. It clattered to the floor.
“Is someone there?” I heard a voice ask.
“Umm, sorry,” I fumbled. “I, uhhh . . .” The stall door opened and Katie walked out.
“You should see your face, Stacey!” She laughed. I fumed, feeling my face flush red.
“Sorry, I just couldn’t resist,” she said. “Okay, to business. Strip and sit.” She indicated the bench that had been my gang-bang platform last night.
I peeled off my work clothes, leaving myself in just my crotchless panties — my clittie, still caged in its bright pink resin cage jutting proudly (?) out front. I crossed the room and sat down, crossing my legs in a feminine manner.
“Perfect!” she said. She ducked into the stall and brought out a shopping bag. “I felt bad for how your pretty panties were ruined so I bought you a few things.” She knelt in front of me, shaking a small bottle in her hand. It was pink nail polish.
“I grabbed it at Ulta,” she said like we were just girls chatting at the spa. “It’s the Sally Hansen Intsa-Dri nail polish — in Pink Blink. Isn’t it just adorable?” She took hold of my right foot and deftly applied a coat to my toenails. She sat back admiring her work.
“Switch,” she said, leaning back. I re-crossed my legs the other way. A dozen swift strokes later both of my feet were tipped in bubble-gum pink polish. “It dries in less than a minute! Cute, right?”
“Yes, Miss Katie,” I said. She indicated that she wanted me to spread my legs.
“Okay, let’s see those hands,” she said. “Put them on your knees.” She inspected my fingernails. “Hmm, not too bad; a little masculine but we can fix that.” She pulled out a file and began shaping my nails. Once shaped she painted them the same color. As she worked she chatted a little about the night’s coming activities.
“I want you looking as feminine as possible tonight. We’re going clubbing at a special spot I found. I think it will be very good for your development. I know we haven’t talked about those 150 Rules for Sissies since I gave you your homework assignment, but I promise you we will soon. In the meantime, I still want to work toward our goal of completing as many of them as we can before your wife gets home!”
Ten minutes in and my fingernails now matched my toenails.
“Okay, just this once I will do your makeup while we make sure your nails are dry.” She expertly put on my face, using makeup from that same bag. As she finished, she looked me over closely. “You look so pretty. Pretty, but with just the right amount of slutty peeking out. Perfect.”
“How are your nails? Dry?” I gingerly touched them.
“Yes, Miss Katie.” She stood back and got out her phone.
“Strike a pose, girl,” she said with a giggle. I posed with my legs crossed and my hands over my knees. I pursed my lips in a kiss as she clicked away.
“Very good. Get your tits on girl! Stockings and shoes too. Chop-chop!” Katie sat on the bench and watched me get dressed.
It was weird, but I felt a little self-conscious dressing in front of someone for the first time — putting on my bra, and adjusting my breast forms in the cups. I rolled my stockings up my legs, checking my seams in the mirror. I stepped into my heels. As I placed each foot on the bench to fasten the ankle straps it brought my caged clittie near Katie’s face.
“Aww, poor baby’s crying chastity tears,” she said. She reached out a finger and wiped the tip of my cage. She moved her finger to her mouth and I thought for a hot second that she was going to lick my pre-cum off her finger. Instead, she smeared it all over my butt plug, using it as lube to ease the cold metal inside of me.
She pulled her bag closer to her and reached inside. She pulled out a pile of pink and held open a skirt for me to step into. It was a micro-mini pleated skirt in pink plaid.
“Isn’t this cute?” she asked. “I picked it up in the Junior-Plus section. That way you get the “girl’s” shorter length in a size that fits your body!” She stood up, holding a lavender shirt. “Here is the first of your surprises. Arms up and close your eyes.”
I closed my eyes and she pulled the shirt on me. As I lowered my arms I felt her adjust the shirt on my frame. It felt like a midriff-baring shirt. “Keep your eyes closed,” she admonished me. “Arms behind you.” As I moved my arms behind me I felt her pull something long-sleeved and satin up my arms. She turned me around and I felt and heard her zip up what I assumed was a jacket.
“Okay, look.” I looked into the mirror. The skirt was so short that there was a gap between my stocking tops and the hem of the skirt. My cage was not quite visible, but when I turned around the barest hint of my ass cheeks was visible. The jacket was pink satin. In black the words “Pink Lady” were embroidered in script over the right breast. “See? Like Grease!” She clapped her hands. “Now sit! Our Uber will be here soon and I still have to change!”
I sat and she pulled the wig cap on my head, followed by the wig. She did a quick finger-styling of the wig and declared me finished. She stepped back and surveyed the results. She took several pictures before getting ready herself.
I sat and watched, feeling my cage leak as she stripped and dressed in front of me. First, she stripped down to her bra and panties — a dark green unlined lace demi-cup bra that showed an impressive amount of cleavage and allowed her nipples to be seen. Her matching lace thong panties barely showed through the black spandex leggings she shimmied into. A black tank top went next, followed by a matching “Pink Lady” jacket. She left the jacket unzipped just enough to show off some of her cleavage. She stepped into a pair of three-inch black patent mules and tied a jaunty scarf around her neck.
“It’s 50s night,” she said. “Like I said, you know, Grease.” She pulled a small pink wristlet purse from the bag. She opened it and held up the things already placed inside, itemizing them out loud as she went. “Lipstick, for when you need a touch-up. Lube, in case you get lucky.” She winked conspiratorially. The last item she held up and let unfold. “Condoms, also in case you get lucky.” She tucked them all back in place and handed me the purse.
Her phone dinged and buzzed.
“Our Uber is here! Let’s go!” She took my hand and led me from the bathroom, holding my hand all the way to the elevator. She pushed the down button and was practically buzzing with anticipation. The elevator stopped on our floor, coming from above. I felt my stomach drop into my toes when the door opened and I caught a glimpse of a man in a suit waiting inside.
“Good evening, Mr. Marshall,” Katie said as she dragged me onto the elevator with her. Mr. Marshall was our CFO and I knew he had a reputation for being both a hard ass and a philanderer. He immediately eyed her up and down like a piece of meat. Then I realized he was eying me up and down as well.
“Good evening, Katie,” he said evenly. “Is this a new employee? I don’t believe we’ve ever met.”
“No, this is my cousin Stacey. She met me here so we could go out clubbing right after I finished work today.” I nodded and swallowed hard. Katie nudged my arm hard, punching my purse from my grasp. I cringed inwardly as I had to bend over to pick it up. There was no doubt in my mind that he was rewarded with a view of my open-ass panties and perhaps a flash of my pink jeweled butt plug. She smirked as he ogled me more.
“We’re just meeting our Uber outside,” Katie said.
“Me too,” he said. “Did you order a ride share to the downtown area, by chance? I’m meeting my wife at Ruth’s Chris for a bite.”
“Uhh, I thought I ordered us our own car,” Katie stammered. “Well, we’ll just have to make the best of it.”
Sure enough, there was only one car waiting for all of us. Katie pushed me to the front so that I would have to load first. I have no doubt Mr. Marshall got quite the eye full as I crawled into the car, probably even seeing my caged clittie assuming he knew what he was looking at. Katie offered Mr. Marshall the middle seat, and she slithered in beside him. I knew she had something already working in the back of her mind.
“Why don’t you girls let me take care of the ride tonight,” he said.
“Oh, Mr. Marshall,” Katie said, “that would be so amazing! Did you hear that, Stacey? Mr. Marshall wants to pay for our trip downtown!” I smiled what I hoped looked like an enthusiastic smile.
“Please, call me Edward,” he said. “I mean, since we’re just three people sharing a ride after work.”
“Oooh, Edward. I like that,” Katie said. “Stacey, I think we might need to find a way to thank Edward, here.” She grabbed his right hand and slid it between her legs. “How does that feel, Edward? Do you like that?” He moaned involuntarily.
“Nice,” he said with a catch in his voice.
“Or do you think this would feel better?” She slid his hand down the front of her pants. It was easy to see that he was already fingering her pussy.
“God, yes,” he said with a noticeable tone of lust in his voice. He placed his left hand on my knee and I felt it slowly slide towards the one area I knew I didn’t want my CFO’s hands to go. There was only one thing I could do to prevent him from finding me out.
I stopped his hand’s advance, pushing it toward him and off my leg. His wounded look changed to a broad smile when my hand snaked its way into his lap, feeling the growing bulge in his pants. I squeezed his hard-on, stroking him through the material. He tried feeling me up again so I took the next logical step to stop him. I unzipped his pants and reached inside, pulling his cock out. It was almost perfectly straight and was raging hard at six inches. I lowered my mouth onto it.
“Ohh, yes, please,” he moaned. His hand moved to the back of my head.
I pushed him all the way in my throat and pursed my lips around the base of his cock, hoping to leave a very noticeable ring of lipstick behind. From my new position, I could clearly hear the squelching sounds of his right hand working inside of Katie’s panties.
“Stacey, you little slut!” Katie exclaimed. Seeing me sucking his cock sent her over the edge. I heard the now-familiar sound of her climax as she clamped her thighs around his hand. Meanwhile, his other hand had moved from the top of my head to my ass, cupping my left cheek before locating and pressing his fingers against the jewel of my butt plug.
I slurped loudly as I began bobbing my head up and down on his shaft, sucking and stroking all at the same time. I did that just nine or ten times before he started bucking his hips. His load was thick and creamy and I had no trouble swallowing it all. I slurped long and hard one more time, releasing his cock when I got to the end. I looked at the driver, who had apparently been watching me intently. I licked my lips and mouthed the words, “You are next.”
“Uhh, Ruth’s Chris,” the driver said, seemingly embarrassed about interrupting the goings-on.
Edward scrambled to put himself together. I noticed a bit of my lipstick around the fly flap on his pants. He was rushing to meet his wife with my lipstick on his crotch and Katie’s pussy juice all over his hand. I so wanted to be a fly on that wall as he greeted her!
Katie jumped out of the car and I followed Edward out, climbing into the front seat. Katie smirked at me as she jumped back in.
“Off we go!” she declared to the driver. He pulled away from the curb as I lowered my head into his lap. “Next stop: The Closet!”
