Sissification 101: Ch. 07

"I think this is a mystery you won't solve until the perp, and I'm calling her that in the best possible way, is revealed to you," Joan predicted as she parked.

"You always do solve them before I do," I sighed, having only once guessed the killer before she had.

"A woman's intuition," Joan shrugged.

"That's something that I suppose no pills or injections will ever provide for me," I joked, as we exited the car.

We walked into the rather posh hotel, where my skanky appearance looked completely out of place, and she said, "Come with me to the washroom, since once we enter her room upstairs, you'll immediately become fully occupied."

"Fuck, I really want to learn what this surprise is," I said.

"Soon," she promised, giving me a wink and leading me into the ladies' washroom... something I'd never been inside before. I was shocked... maybe it was because it was a posh hotel, but this women's bathroom was way more spacious and nice than any men's. "I'll be back soon," she said, stepping into a stall.

I went into one too, and indeed just like any other woman, I sat down to go pee and needed to wipe afterwards.

I got out, washed my hands and waited for Joan, who was taking longer than she usually did. Once she came out, I understood why. She had changed out of her casual shopping outfit, which she was now carrying in a shopping bag I hadn't noticed before, and now was wearing a trench coat, black boots, and I could see just a glimpse of her black stockings.

"I'd like to see what's underneath that coat," I said. "Are you naked?"

"Maybe. Does the thought get your clitty all excited?" she asked.

"You always do," I said, which was true.

"You're so sweet," she said, as she leaned in and kissed me... just as two 'other' women entered the bathroom.

"Oh my," one of them said.

Joan ignored them as she leisurely completed our kiss before reaching into her purse and saying loud enough to be heard, "We'd better freshen up your lipstick for our Mistress and Master."

Joan did love shocking people, as the two women went into their chosen stalls looking scandalised. Joan refreshed my lipstick as I pondered this new piece of information: a Master would be present. Carter? Somehow I didn't think so.

Once done, she said, loud enough for the two prudish women to overhear like it or not, "Now those lips are just made for a big black cock to face fuck."

"Jesus Christ," the woman in one of the stalls objected.

"Unless ma'am, you'd like my girlfriend to go down on you first," Joan offered.

"Just get out of here, before I call security," the woman retorted.

"I'll take that as a courteous 'some other time'," Joan said.

I added, my voice deliberately revealing I was a man as we walked out of the washroom, "Your loss, ma'am."

"That was a man!" the other woman gasped as we sauntered out, going directly to the elevator, where an older black couple were waiting.

My first thought was, What are the odds these two are part of the surprise?... I then shook my head at the realization that these days whenever I saw a black man, a black woman or a black couple, I just assumed they were there so they could use me as they pleased.

The elevator opened and as we got in, the older couple noticed my outfit; I received dubious looks from both of them, as Joan pressed the button for the top floor. So no, this couple wasn't part of my surprise.

The back couple got off on the fifth floor, and once the door had closed behind them, Joan asked, "Ready?"

"Always," I said, excited to find out who the mystery woman was and what my 'epic' surprise was to be, as the elevator continued its way upwards.

We got off on the top floor and went to 1401. She stopped outside the door and texted something to someone. "Just have to make sure they're ready for us."

"You have me on pins and needles," I said, the butt plug still in my ass, barely held in place by the delicate excuse for panties I was wearing.

She said nothing, but just stared at her phone... a bit nervously I noticed... until it binged. "Well Erica, here goes everything."

She took my hand and opened the door.

A million different scenarios had swirled through my head about what could lie behind this door... but nothing in my wildest, wickedest dreams could have prepared me for what I walked into.

First, the hotel room was huge... a complete suite.

Second, the first detail I took in was a naked and very tattooed black man sitting on a couch while someone dressed as sluttily as I was sucked his cock while he drank a beer. At first I didn't realize the cock sucker was a fellow sissy... but I would soon discover her true identity, which would rock me to the core.

Third, as the shocks began growing, I saw Denise, Joan's older sister, sitting on another couch, dressed in black leather dominatrix gear that consisted entirely of straps, resulting in for instance her breasts being supported, but completely uncovered. I assumed the same was true of her pussy, since there was a blonde person busy between her legs... the blonde with a dog tail anchored in her ass, licking away... again at first, I couldn't tell who the lucky girl was who was lapping away at the beautiful and busty Denise... Joan's sister's reddish-blonde hair really standing out in the all-black leather.

Fourth, I turned around to see Joan shrugging off her trench coat and revealing that she was wearing the exact same attire as Denise... her breasts too beautifully displayed, and she had somehow been concealing her eight-inch strap-on (which judging from the smacking sounds the blonde was making, Denise was not wearing one of).

Fifth, Denise said, "I can't wait to make you into my cunt-licking bimbo slave."

"Me?" I asked.

"Well, you too of course," she smiled, as she combed her fingers through the perhaps-girl's hair, who I couldn't see clearly... the dim lighting in the room not helping matters. "But, no, tonight Joan and I go will head-to-head."

"Well, our sissies will on our behalf," Joan corrected her.

Sixth, earlier in the day Joan had said something about 'if I won,' which meant I was about to take part in some sort of sissy competition. And which also meant that at least one of the submissive girls in the room... wasn't one.

"True, our sissies will," Denise said, glancing towards the person sucking the black man's cock... who I also couldn't see well, except that he or she was white. "Isn't that right, Michelle?"

Seventh, "Yes, Mistress," the cock sucker said, although his voice made me gasp. 'Michelle' was now revealed as Michael, Denise's stockbroker husband.

"Think you can beat Joan's sissy in some competitions?" Denise asked him/her.

"Of course, Mistress," Michael or Michelle said, glancing at me... he too wearing bright pink slutty clothes and make-up. "I'll beat her easily."

"Are you gonna let her dismiss you like that?" Joan asked me.

I was still processing all this, when Denise said, "Slut, go get my strap-on for me."

Eighth, "Yes, Mistress," a female voice said from between Denise's legs, another voice I recognized... it was Jeanette... Joan and Denise's baby sister. Their shy, quiet sister who always dressed so demurely that I couldn't say for sure whether she had any tits.

Until now, that is. I watched as Jeanette turned away from her sister and crawled, the tail still in her ass and a nice pair of C-cups swaying nakedly beneath her chest, over to a bag on the far side of the room, where she extracted a strap-on, placed it in her mouth, and crawled back to her sister.

"Michelle, stop sucking Master Jones, and come to me," Denise ordered.

"Yes, Mistress," Michelle said, crawling over to her, as I glanced across and saw that Master Jones had a huge fucking BBC. It must be twelve inches when fully erect, which it was. And when I looked over at Michelle, I saw a clitty just as tiny as mine, also trapped inside a metal cage.

"Kneel, Erica," Joan ordered.

"Erica, this is Master Jones; he is Jeanette's professor at college, and her Master whenever they're in private," Denise informed me. Then added, "Although she's also my slut, so sometimes he's willing to share."

"Hi, sir," I said, and then added, "you have a magnificent cock."

"Thank you miss," he said, as it extended upwards from his groin like the most appealing bar of chocolate ever.

"So Erica, the two of you will compete in a series of sissy tasks, and whoever loses will become bottom bitch, and her Mistress will become the bottom bitch for the other Mistress," Denise explained

"So if you lose, I'll have to submit to Denise," Joan said.

I wanted to point out how I thought she'd like that, but perhaps I wasn't correct. Sisters could have quite the rivalry. It did make me wonder however, how long Joan had known Michael was a sissy, and how that connected to my own sissification. I recalled that the first evening she'd queried me about my sissy predilections, she'd been surprisingly conversant with the nuances of the fetish. "I understand, Mistress."

"So don't fucking lose," Joan said.

"Oh, she's going to lose, never fear," Denise said confidently "Your sissy has only a few weeks' experience, while mine has been a sissy slut for years."

"We'll see," Joan said, showing the utmost confidence in me... which made me determined to win.

"Task one is a fashion show. We'll see who dolled up their slut better, with Master Jones making the one and only vote," Denise said.

"Stand up, sissies," Master Jones said, as he took a sip of his beer.

Both of us stood up.

"Michelle, pose for me," the black tattooed stud ordered.

"Yes, Master," Michelle said, and she pranced around looking very feminine, wiggling her ass, and more. She was dressed in a cheerleader outfit and I have to admit, with the wig and huge tits packed into the tight varsity sweater, she could easily pass for a woman. Even for a very hot woman.

"Good," Master approved. "Your turn, Erica."

"Thank you, Master," I nodded, as I sauntered over to him, but was so nervous I stumbled and fell, landing on top of him. "I-I-I'm so sorry!"

"Quite the graceful sissy you have, Joan," Denise laughed, as I struggled my way back to my feet.

"Well, obviously the first point goes to Michelle," Master Jones judged.

I sighed and whispered, "Sorry, Mistress."

"Just be sure to win the next event," she said, looking at me with annoyance for the first time ever.

"I guarantee it," I said, even though I had no idea what the next task was.

"Task two is to demonstrate which of you can hold a ten-inch strap-on cock balls deep for the longest time," Joan announced. "Each sissy will suck her Mistress's competitor's cock."

Michelle crawled over to Joan, and I crawled to Denise. "You know? I knew you were a faggot the first time I met you," Denise said to me.

"Says the woman who married a guy who in high school had more dicks in him than the entire cheerleading squad," Joan countered.

"Let's get this going," Denise said, it seemed not liking to be challenged.

"On the count of three, take the cock all the way into your mouth, and hold it there for as long as you can," Joan explained. "The one who lasts the longest wins the point."

"Don't even bother trying to win, faggot," Denise said. "My sissy can deep throat all night."

"I can go for days," I bluffed, never having done so, but taking her challenge.

"Jeannette you watch Michelle, and Master Jones you watch the faggot wannabe sissy," Denise said, trying to rattle me with her belittlement ... somehow not being aware how any kind of humiliation only enhanced my excitement, and my determination to earn more of it.

"Yes, Mistress," said the cute Jeannette, looking stunningly hot, completely naked except for a garter-belt and red stockings.

"Sure," Master Jones agreed in his deep, dominant voice.

"Three, two, one, deep throat," Joan counted down.

Having sucked so many black cocks recently, I didn't find deep throating ten inches remotely difficult... although in the past I'd never be able to hold it in place tickling my tonsils, for more than a few seconds.

"Any moving away at all, and you're out," Denise added after a few seconds.

I just had to win this one! I had no idea how many tasks there were going to be, but I figured that falling behind two to nothing wouldn't be good for me at all.

"Erica can do this all night," Joan bragged falsely, partly to rattle Michelle, but also I assumed to keep me focused. "He sucks a dozen-plus black cocks every week." That last bit was absolutely true.

"Well he is only a faggot," Denise said.

"And what, pray tell, is the difference between a sissy and a faggot?" Joan asked archly.

"Erica is," she answered.

"Whatever," Joan said. "My sissy, my faggot, my whatever you want to call her... will hold that cock of yours deep in her mouth all night if you let her."

"As will mine," Denise said.

"Come ride my cock, slut," Master Jones ordered Jeanette, getting bored quickly at this task, which was completely uneventful except for the back-and-forth catcalling.

"Yes, Master," Jeanette replied, sounding very excited... as I would be too... since I was indeed a faggot... a faggot for black cock... and I would do anything to suck a BBC, or to get fucked by a BBC.

"Don't let him come," Denise warned, "his seed will be needed for a later challenge."

"I won't, Mistress," Jeanette agreed.

"And when did you make our baby sister into your slut?" Joan said, her tone revealing that her younger sister's presence and participation tonight was an unexpected surprise.

"Recently," Denise answered, before adding, "and I'll be adding a second baby sister to my stable very, very soon. Her eighteenth birthday is in a month, you know."

"Or I'll be taking our youngest baby sister away from you," Joan threatened.

God, listening to these two bicker was so hot!

Suddenly Michelle gagged, and Joan said, "Your faggot has lost this round."

"Sorry, Mistress," Michelle said, obviously devastated to have lost.

I kept Denise's cock in my mouth, planning to keep going until she made the decision to pull it out... just to make a point.

"Like I said big sis, she can go all night," Joan said.

"Oh fuck," Jeanette moaned, swearing for the first time I'd ever heard... unlike Denise and Joan, who each had very foul mouths... which was being proven again tonight.

"Fuck," Denise sighed, pulling her cock out and admitting to me, "fine, you win this one."

I instantly withdrew and turned to watch as Jeanette had her nylon-clad feet resting on Master Jones' strong black legs and was bouncing on his cock... it was one of the hottest, most impressive positions I'd ever seen... porn included.

"When will your friends get here?" Denise asked.

"Whenever we like. They're downstairs in the bar," Master Jones replied.

"Call them up then," Denise said.

"Will do," he said, reaching for his phone. After a moment he said simply, "Come on up."

"How many tasks are there?" I asked, wanting to know how many of them I needed to win.

"Five," Denise answered. "Unless you lose the next two in a row."

"Not happening," I said, gathering confidence from my recent victory.

"We'll see," she smirked, looking down at me.

"Yes, we will," Joan said, as we suddenly all turned to watch their baby sister take twelve inches in her petite frame, bouncing away as if she was a professional gymnast.

"She may be the biggest slut of the three of us," Denise observed.

"Well, she learned from the best," Joan said, and I couldn't tell whether that was a shot at her slutty older sister, or a compliment incorporating both of them. Probably the latter, I decided. She'd never criticized me for being a slut, but instead always heaped on the praise.

Denise also took it as the latter saying, "At least there's one thing all three of us can agree on."

"That we'll do anything for a big black cock," Joan said as if by rote.

"Exactly," Denise nodded, seeming to be as captivated by that black cock as Joan and I were.

Big black cock... the universal equalizer among enlightened white men and women.

"So, task three is simply seeing which of you can get off three black guys the quickest," Denise said.

"Only three?" I asked, trying to come across like I had black cock for breakfast, lunch and dinner... which, for the record, I had done; just not every day.

"And you tell me he isn't a faggot?" Denise asked, looking at my sister.

"I didn't claim Erica wasn't a faggot for BBC," Joan clarified. "I'm just saying so is yours... although I know he'll also suck white cock or any cock he's given, which makes him a bigger faggot than mine."

"He'll suck any cock I tell him to," Denise clarified.

"Because he's a faggot," Joan rebutted. "And he's one for any old cock, while my sissy is a connoisseur of only juicy, big, black cock."

"Once you become my slut, your faggot will be sucking every cock in town," Denise threatened. "Fat college virgin cock, old man cock at the nursing home, and even dirty unwashed cock down on Alpine Street."

That third possibility most definitely did not appeal to me... maybe fat college virgin cock and old man cock if they were black... there's just something impossible to resist about any black cock... but homeless cock, which was the kind living on Alpine Street, well... that was pushing it.

"I'd threaten that with your faggot, but I'm pretty sure you already take him to those places," Joan countered, neither of them backing down in their game of rapidly growing high stakes.

There was a knock at the door interrupting the back and forth banter, and Joan went and answered it. Six black (thank god) studs, all of college age, walked in.

"Holy shit," one said, seeing Jeannette bouncing on her Master's cock.

"Line up boys, in two rows of three," Denise ordered.

"Sure," one said, checking out her tits.

"Pull down your pants, studs," Joan said.

"No problem," another said, as they lined up in two rows of three.

"Thanks for offering your big cocks for our sissy competition," Denise said.

"No problem," one said, and added, "although sexy lady, you sure you don't want to settle yourself into the middle of a nice Oreo?"

"Enticing," Denise nodded, "and definitely a plan for another day when my two sisters and I will show up and you six can gangbang us all night, but today is about our sissies."

"Then we'll be expecting you sluts," one said.

Joan added, "Oh, I'll be happy to take on all six of you myself, just about any day you like."

"Fuck Benny, are these women for real?"

Master Jones, whose given name must be Benny, nodded, "One hundred percent."

"Well, I can't think of anything nicer."

"Sissies, pick your line," Denise ordered, and we each crawled to the three cocks closest to each of us. (Yes, I know I'm objectifying those guys, who most likely have many splendid qualities, but I didn't hear them complaining at the time, so get over it.)

I considered that in many ways this contest could be determined by the luck of the draw. It was partly skill and enthusiasm, etc., but it could also be seriously impacted by the endurance of the cocks. (Had any of them already come today? Did any of them have a quick trigger release, or the reverse... amazing stamina?)

"The rules are simple, sissies," Denise said. "The first one of you to swallow three loads is the winner, and she moves to within a single victory of winning the entire competition."

"Sounds simple," I said, staring at the first black cock before me... eight inches and thick. Nice!

"Oh it is," said the guy whose dick was before me. "Just suck me good, swallow your treat, and move on down the line."