Hypnosissy: Chapter 11

by silkstockingslover

Brian discovers he really loves getting fucked.

WARNING PLEASE READ:

Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist in the first place.

Note 2: Of course, all participants are at least 18 years old and beyond legal age.

Note 3: Thanks to Tex Beethoven and Robert for editing.

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Wednesday:

When my alarm went off the next morning, I woke up on top of the covers and still dressed. I really couldn't afford to miss another morning of school!

I got off the bed, got undressed, and saw cum stains on both the front and back of the pantyhose. I'd obviously oozed out some cum from my pitifully caged clitty, and also a fair amount of Mr. Mulroney's cum had leaked out of my pussy, creating a larger dried spot.

I took them off and hid them under my pillow; I'd have to deal with laundering them later.

I went and showered, and then as I was walking past my parents' room, I felt compelled to filch another pair of Mom's pantyhose. I looked around, didn't see anyone, so I scurried in, grabbed the first pair I saw, mocha coloured ones, and hurried back to my room.

I put on my only thong, figuring I'd secretly be dressed extra feminine when I met Rose's parents in their home tonight... and then put the pantyhose on over it. I wasn't certain whether I'd keep them on for the evening's dinner party, but I felt compelled to wear them at least for now.

I slid into some jeans and a sweatshirt... and went down to have breakfast.

I chatted with my parents, and then headed to school.

Just as I reached the school, I received a text.

It was from Mr. Watson: Good news. If you are still interested, I have your official invitation to be initiated into The Club.

One brief text, and my clitty woke up.

I responded, not even pondering how this could be anything but good news: Sounds great! I am definitely still interested.

Mr. Watson responded as I got out of my car: Great. I will send you the details later, but it will begin at 8PM this Saturday.

I responded as I walked into the school: Perfect. I'll clear my schedule.

There was no response, but I accidentally bumped into someone while I was still checking my phone.

It was Hernandez... a nerd... and I wondered if I'd secretly sucked his cock last weekend at Elmer's glory hole. He turned around and looked at me fearfully. Whether I'd sucked him or not, he obviously thought I was still the same arrogant bully I'd been until a couple of weeks ago.

I said mildly, "Sorry, Hernandez, I wasn't paying attention to where I was going."

"Stay out of his way, you," Josh, a senior receiver on the football team stepped in and barked, giving Hernandez a shove.

No longer being an insensitive jock, and still with my attention on the reasonable possibility I'd sucked his cock recently, I said to Josh, "Leave him alone, man. I'm the one who walked into him."

"So what? He should stay out of our way," Josh said, glaring at Hernandez, who looked like he might piss his pants.

"Seriously, man," I insisted. "Leave him alone!"

"What's the matter with you?" he asked, still looking a bit angry, but now irritated with me, as Hernandez scurried away.

"Nothing," I said. "Why are you picking on someone who didn't do anything to you?"

"Because I can, of course," he said. "And when did you become a pacifist?"

"Just leave him alone," I said, and walked away.

"Jesus Christ!" Josh said.

I was in class watching a boring ass video, when I received a text from Eugene: You stood up for Hernandez. Good job. If you want a reward, you can meet me in Mrs. Walker's classroom at lunch.

Mrs. Walker was a hot English teacher I'd frequently imagined fucking. She always wore dresses or skirts, and always with pantyhose. She was a MILF I'd had my eyes on fucking before I graduated, until Rose happened.

I responded: Will that be private enough?

He replied: Yes. Do you want a treat or not?

I responded: Yes.

"Brian, is there something on your phone you'd like to share with us?" the teacher asked.

"N-n-no," I stammered, closing my text messages. But then my phone visibly vibrated while it was still in my hand.

"I think I'll check that message on behalf of the class," he said coolly, approaching me.

I quickly locked my phone, and then I handed it to him while it buzzed again. He looked down at it and then back up at me. Expressionlessly.

Then, still completely cool and unreadable, he walked away.

Fuck!

For a few seconds, he'd have been able to see whatever message it was. What if it was something incriminating?

Fuck!

Fuck!

Fuck!

For the next forty minutes, I worried and fretted.

I respected Mr. Mills; he was a good teacher, although he was rather stern. I prayed the text had been from someone else... anyone... well, not absolutely anyone... since at this stage of my journey there were any number of people who could be sending me inappropriate texts.

When the bell rang, I went to Mr. Mills' desk, and he handed me my phone.

"I'm sorry for disrespecting your rules, Mr. Mills," I apologized.

"It's alright," he said, and since we were now alone, he then said, "But tell me: do you play golf?"

My cheeks went red as I replied, recalling this weird, secret, two part passcode Mr. Watson had mentioned, "I like holes in one."

"Interesting," he said, as my cheeks burned with embarrassment at being outed to him, and yet feeling relieved that he belonged to this secret society.

As a new batch of kids began entering the room for the next period, he instructed, "Come and see me after lunch in my spare. I'll write you an excuse from whatever class you have."

"Yes, sir," I nodded, wondering what might transpire at that time.

"Now go," he waved me away.

I walked out, checking my phone.

There were four messages I hadn't seen before... Mr. Mills could have seen all of them... since he'd checked my phone twice that I'd noticed during the rest of the period, and I could have easily missed his checking it once more.

The newest was from Rose: I'll pick you up at 4:30 at your house. Dress nice. Suit and tie. And panties.

Panties. Okay, that one wasn't good, but it would be far worse if Mr. Mills wasn't in The Club.

I responded: I'm in my thong today. Does that work?

I decided not to mention I was also wearing pantyhose... since I wasn't sure whether that would turn her on or make her think I was too gay... although based on all those sissy videos she'd been giving me to watch, I was 99% sure she'd be fine with it.

The second newest was from Mom: Are you coming home for dinner tonight?

I responded: No, I'm going to meet Rose's parents, but I will be home for a while after school.

The third newest was from Camry: Hey, cock sucker. Glory hole needs someone at break. Want a couple of loads?

I decided not to worry about Mr. Mills since we both 'played golf', and responded, my mouth salivating in expectation of all the cock I'd be getting today. A couple of loads at break, Eugene at lunch, probably Mr. Mills in the afternoon. It was shaping up to be a good day: I'll be there.

The one that must have prompted Mr. Mills to take my phone away was from Mr. Watson: Great. I'll make it happen. Also, if you're hungry, I have a prep next period.

His number was displayed, but it wasn't a contact, so there was no way Mr. Mills could have gotten much from that... unless he could read between the lines. And given he belonged to The Club, he very well could... but again, it wasn't a problem.

I responded to Mr. Watson, and started heading towards his classroom instead of mine: Be there ASAP.

While I was relating to those ones, a new text came in from Eugene: Be there as soon as the bell rings. I got shit to do at lunch, but you deserve a reward for being a good girl.

I responded to Eugene: Thanks. I'll be there ASAP after the bell, and my class is in the same hallway.

I reached the auto shop classroom, walked in, and headed to the back of the room, where he was washing his hands.

"Hi, Mr. Watson," I greeted.

"Hey, got time for a quick chat?"

"Yeah, I'll be late for class, but whatever," I shrugged.

"I'll write an excuse for you," he said, as he walked into his office and I followed. "Close and lock the door."

"Yes, sir."

"You don't have to call me sir in private," he said. "I suck as much cock as I get sucked. I'll suck yours right here and now, if you're out of that cage."

"Nope," I sighed.

"How long before your bird flies free?" he asked, seeming concerned.

"Don't know," I shrugged. "But I'm seeing her tonight."

"I see," he said.

"I don't mean to rush you, but I slept late and missed yesterday morning's classes, so may I suck you right away?" I asked, still finding the crazy situations I found myself in, and the outlandish words coming out of my mouth on a regular basis, pretty unbelievable.

"Yeah, sure," he said, pulling his jeans down. I dropped in front of him, pulled his boxers down and took his cock in my mouth. The first one of the day.

I can't explain why, but after being on edge all morning, the moment I was on my knees with a cock in my mouth, I felt at ease.

I swirled my tongue around his flaccid cock, working on getting it hard.

"Oh, I like that," he groaned, as he hardened in my mouth.

"Mmmmmmm," I moaned, my new go to response whenever someone said something to me while my mouth was filled with cock.

"Yeah," he groaned.

Once he was hard, I gave him my fast suck version, deep throating him easily, and creating the extra saliva needed to bathe his cock lavishly.

In only three or four minutes he warned, "I'm about to bust."

I responded with my usual, "Mmmmmmm," and then deciding I really wanted to taste his load, backed off and said, "Come in my mouth, instead of my throat; I want to taste your yummy load."

"Sure, kid," he said, stroking his cock while aiming it at my wide open mouth.

A few strokes later, he was shooting his cum into my open bulls eye, although a bit of it drifted down onto my chin and sweater.

"Fuck," he grunted.

Once he was done, I closed my mouth and swished the load back and forth like a viscous mouthwash, enjoying its gooey texture and salty taste, before I swallowed it all down, and took his cock back in my mouth.

"You really are a great cock sucker," he said approvingly.

After a few seconds, I let his cock slip out of my mouth, stood up and said, "Words that a couple weeks ago I would never have imagined hearing."

"Yeah, that first cock must have changed everything," he said, understanding my lust and my weakness.

"Tell me about it," I said, as I scooped a wad of cum off my sweater and popped it into my mouth like the cum craving addict I was becoming.

"Wait until your initiation," he said.

"I can't wait," I said. "I understand Mr. Mills is also in The Club."

"If he were, how would you know?" he asked guardedly.

"He confiscated my phone in class this morning, saw some text messages on it, and then after class we discussed golf," I answered, as he put his cock away.

"I see," he said.

"It's okay to mention it to you, isn't it?" I worried. "Since you're both members of The Club, and I'm about to join it?"

"Oh, certainly; no problem," he reassured me. "Did anything come from your mutual recognition?"

"Yeah," I said. "I'm supposed to meet him during his preparation period right after lunch."

"He likes to fuck bottoms," he warned.

"Well, since the last time, back when I told your friends I didn't take it in the ass..." I began and then stopped, once again realizing how gay I was sounding.

"You now take it in the ass?" he asked.

"Yeah," I admitted sheepishly. "Although only a couple times so far."

"Then I imagine there's a good chance that count will increase in a couple of hours."

"Do you feel ashamed after you get fucked?" I asked.

"I used to," he said. "It's pretty unavoidable at first, since it takes some time to process it and reach the point of accepting without any reservations who you really are, and who you're meant to be."

"Most of the time I'm fine with it," I said. "But sometimes I feel extremely guilty or ashamed."

"Well, I can only speak from experience," he said. "Luckily, things have changed a lot from when I was first discovering my love for cock. My first cocks in the 60s were black, and back then, being gay wasn't tolerated by just about anybody. But worse, being a black cock sucking bottom for the butler and help was enough to get a young blood disowned!"

"You were disowned?" I gasped, thinking back to stories about how much race relations had changed in the last sixty years, although in some ways nothing had really changed, since just about all black people still had good reason to fear for their lives around the police, sometimes even if they were only stopped for speeding.

"No, but that was only because my Dad was also a willing cock sucker and bottom for BBC, although I didn't find out about it until years later," he said. "So I wasn't only questioning my sexuality, but also my place in the world, since I couldn't resist the temptation of the almighty cock from the time I was eighteen. For instance, one day I sucked every male member of one of my Dad's employees family at their reunion, which had over forty brothers in attendance."

"Wow!" I said, that marathon sounding amazing.

"Yeah, I was spit roasted a dozen times, and I took over sixty loads into or onto me that day. And that night too, since we kept going until dawn."

"Amazing," I said.

"Yeah, in retrospect it really was," he said. "But eventually I figured out that whenever I'd finished swallowing a load or getting fucked, I only felt any shame and guilt because of what society kept telling me I was supposed to be. Often the term 'real man' has some really harmful definitions."

"I understand," I nodded.

"So in the 80s, I finally came to grips with who I was after years of trying to deny my cock lust to myself, and I haven't looked back. There needn't be any shame in accepting who you are."

"Ya think?" I asked.

"Yes, and I'm serious," he said. "You're lucky the times have changed for the most part, although cock sucking and gay sex is still somewhat taboo and underground. But you're only eighteen instead of in your forties, and you already know who you are. So try to accept it. There's no shame required."

"I guess," I said dubiously.

"I know. Marianne Williamson once said something like, 'It's a long journey from the head to the heart.' And she was right: accepting a truth into your mind is a helpful first step, but it doesn't get very useful until you know it in your gut. But affirmations can help you get there. So say something affirming," he said. "Tell me you're a cock sucker and you're proud of it."

"I'm a cock sucker and I'm proud of it," I said, not too convincingly.

"Again," he said. "And this time say it you like you mean it."

"I'm a cock sucker and I'm proud of it," I repeated, this time with a tad more bravado.

"Better," he said. "Another thing that helps is discovering almost no one is who they seem to be. Not just as a theory, but seeing it in actual people."

"How so?"

"Well... just like there's a gay male secret society, there's also a secret lesbian society, and a quickly growing swinging society both in this city and in the world," he said. "All of them secret, but all of them gaining momentum, and someday they won't need to be secret."

"Really?" I asked, Mr. Watson surprising me with stunning revelations every time we got into a chat.

"If you pass your initiation this weekend, and then join in the gay orgy the next weekend, you'll see for yourself there are lots of very prominent men who suck cock, who get fucked, and who get used or who use other men. Politicians, lawyers, teachers, doctors, celebrities..." he listed.

"This is a lot to take in," I said.

"Yeah, but you don't have to absorb all of it at once," he said. "But my main point is, the people who are full of shame are the ones who don't accept who they are, and who deny the temptations inside them," he said. "But you, whether you've mentally acknowledged it or not yet, have already accepted this is the real you. Sometimes Ms. Williamson got it backwards: the truth can be awakened in the heart, then it needs to work its way into the head. And I think that's what your girlfriend is helping you to achieve, and you're almost there. From what I can see, you're already at home in yourself, or at least you are most of the time."

"I am?" I asked.

"Aren't you?" he asked back.

"I guess I am," I admitted. "Most of the time."

"It takes time to completely accept who we are," he said. "But you're well on your way."

"Thanks," I said.

"I'm always here to listen, Brian," he said. "Or to get sucked, or to fuck you, or once that cage is removed, to suck your cock or to get fucked."

"Good to know," I said, this entire conversation having been not only clarifying, but also surreally relaxing.

"Get to class," he said, writing a note and handing it to me.

"Thanks," I said.

"Yeah, anytime," he said.

I went to class pondering his philosophy and advice. There was no doubt I loved cock. No doubt I'd do almost anything to get it... in fact, I seemed to be proving that day in and day out. I just needed to keep reminding myself I didn't need to be ashamed by any of this. And even if I was feeling ashamed, that wasn't the only thing I was feeling.

At breaktime, I went back to the glory hole, where I sucked two teachers' cocks... none of us saying a word... one cock was small and it came in like two minutes, and the other one was seven inches or so with a wild side curve, and that one eventually took charge and fucked my mouth until I swallowed its load.

"Fuck, it's hot watching you suck cock," Camry told me.

"Do you say that to all the cock suckers?" I joked as I stood up.

"Nope," she said. "Nobody's as much of a cum whore as you are."

"Thanks... I guess," I said. Statements like that were typically used to humiliate someone, yet as I reminded myself of Mr. Watson's words, I figured not only it was a compliment, but she'd meant it as one.

At lunchtime following another boring class, I went into Mrs. Walker's classroom, a little nervous she'd be there... but she wasn't.

"Close the door," Eugene said.

I did.

"Quick," he said from where he was leaning back against the wall. "Get over here."

I went to him and dropped in front of him, and he said, "This is your final free load."

"Free load?" I asked as I fished his cock out.

"Yes, the next time you want my cock, it goes in your ass."

"Okay, no problem," I said without hesitation, as I took his cock in my mouth.

"No problem?" he asked, surprised by my answer, and likely by how casually I'd delivered it, as I began to bob.

He used a hand on my forehead to push me away so I could answer, and he asked, "You take it in the ass now?"

"Your sister pegged me last Friday, then she had her shemale friend fuck me the following evening," I said. "The reamings didn't kill me, and I even enjoyed them."

"Alyssa," he nodded.

"Yeah, and then last night in a back alley, a guy railed me while I was bent over the tailgate of his pickup truck," I added, not sure why I was offering him so much information, especially when I'd felt so unwilling on Saturday morning to tell him about my pegging.

"Nice," he said, looking at his watch. "Butt... it will have to wait for now. Butt... I'm fucking your ass real soon."

"I hope so," I said, meaning it, and then I took his cock back into my mouth.

"You really are a faggot now," he said, for once sounding more impressed than condescending.

As usual, I moaned on his cock as I bobbed.

"I mean, there are some great cock suckers at school, and some pretty good bottom bitches," he said, as I devoured his cock with cum hungry lust while listening intently, "but none of them have gone from the top of the school's popularity roster to a two hole cum bucket for any cock they can find, in just a couple weeks."

"I blame you and your sister for all of it," I joshed, after ever so briefly taking his cock out of my mouth.

"I'll happily take my share of the credit," he said affably. "But remember, no matter how many cocks you suck, or how many dicks you hunt down for banging that muscular ass, I'm top dog."

When I didn't respond, he pushed my head away again and asked, looking intently down at me, "Do you understand?"

"Yes," I said.

"Yes, what?" he asked, slapping me in the face with his cock.

"Yes, you're my Master. I'll do whatever you say, and I'll suck you or let you fuck me wherever and whenever you want," I babbled mindlessly, sounding like a complete faggot. "My mouth and ass... or pussy, whatever you want to call it... is available for your pleasure twenty-four seven."

"Shit," he said, clearly impressed by my sudden and way over the top capitulation.

Yet wanting to prove it to him, so hungry for his cock, I added, "In fact, I'll bend over right now if you like, and you can bury your load in my ass."

"That's fucking tempting," he said. "It really is. But it will have to wait."

He slid his cock back into my mouth, and obviously turned on by my nasty submission and reassurances, he fucked my mouth very roughly.

I moaned on his cock throughout the brief couple minutes of face fucking, before he grunted and spewed his load in my mouth.

When he pulled out, I said, still in full sissy submission mode, "Thank you Master, for allowing me to suck your cock and swallow your load."

"Shit," he said, pulling me up, spinning me around, pushing me against the wall he'd been leaning against, and kissing me.

Even after all the slutty things I'd done in the last two weeks, all the cock I'd sucked, all the loads I'd taken, even the sodomy, I wasn't expecting this!

Nor did I ever think I'd respond to a guy's kissing me by kissing him back. But I did!

It was only fifteen seconds, give or take, before he broke our sensual kiss and walked away... leaving me alone in the classroom, my imprisoned cock once again trying to break free, as I tried to process what had just happened.

I shook my head, stunned that I'd allowed a man to kiss me, and even more stunned that I'd kissed him back. And I was completely bewildered that it had felt... really good.

Fuck!

I wiped my face with my sweater to make sure I had no cum on my face (I did), and headed out and into the cafeteria, and I spent the rest of the lunchtime with some of my teammates... attempting to regain at least a little of my masculinity.

Josh was among the group, and he asked, "Are you done having your period, Brianne?"

"It's still Brian thank you very much, and all I was saying is you don't need to go around bullying everyone who's smaller than you are," I repeated my stance on the subject.

"Says the guy who stuffed Gary in a locker last year, and left him locked up in there," he taunted.

"Yeah, that was really shitty of me," I said, not making any excuses for it. Gary had actually transferred to another school for his senior year, and I'm sure I was the main reason.

"It was hilarious," Josh pointed out.

"No, it was an asshole move," I disagreed.

"So when did you grow a vagina?" he asked.

"It's that college chick," Wally said. "He's gotten himself completely pussy whipped."

I shrugged, "Call me what you want. I have an amazingly hot college girlfriend who does things for me the high school girls around here don't even know are possible." Like caging me and training me into being a two-hole cum slut, I didn't mention.

"For instance saying no," someone joked.

"Yeah," I laughed, back in my suave cocky element, even while the taste of Eugene's cum still lingered in my mouth. "I'm dating a hot college girl who always says, 'Not now honey, I have a headache'."

"You have been acting weird," Harry mentioned.

"How so?" I asked, curious about how these guys were perceiving me, after all I'd gone through recently.

"No idea," he said. "Just different."

"Well, I'll take that pearl of wisdom under advisement," I said. "Anyone else have any personal critiques for me to better myself with?"

No one said anything to that, and the topic shifted to the best colleges for football.

After lunch, I headed to Mr. Mills' classroom, instead of to my actual class. I entered, and he waved me in, saying, "Close the door."

"Yes, sir," I said, closing it, and noticing there wasn't a lock on it.

I walked up to his desk and knelt, and he asked, "So how long have you been a member?"

"I'm not."

"Excuse me?"

"I mean not yet, but I'm being initiated Saturday," I explained. "I was just informed which day this morning."

"I see," he said. After a pause, while he seemed to be gathering his thoughts, he asked, "And how long have you been living this... lifestyle?"

"A couple of weeks."

"Only a couple of weeks?"

"Yes, but it's been a crazy couple of weeks."

"How so?"

"Well, during that time I went from being a homophobic asshole, to being very definitely not homophobic," I answered, as we both beat around the bush, without mentioning what we both knew we were talking about.

"The word is gone."

"Excuse me?" I asked, confused.

"It's 'I've gone from being a homophobic asshole, to being very definitely not homophobic'," he corrected me. "Not went."

Oh. He was only correcting my grammar.

"Sorry teach, I've gone from went homophobic assholery, to very definitely assholery that's not at all homophobic no longer," I rephrased the sentence 'correctly', with a smirk.

"Proper grammar is the foundation of our language," he said, which he said almost daily in class. Ironically, he wasn't an English teacher, but a History one.

"Yes, sir," I agreed.

"So do you prefer being the one doing the worshipping?"

"I do," I nodded.

"I see," he said, still with neither of us clearly saying what we both knew we were talking about.

Finally frustrated with this song and dance, I said, "I don't mean to rush this conversation, sir, but I actually have a class, and I was hoping to suck your cock, swallow your load, and then get back and join that class."

"Brian," he gasped, his face displaying complete shock, "what on earth are you talking about?"

"Y-y-you're not a member?" I stammered, instantly mortified and humiliated... and watching my entire life crumbling before my eyes!

"A member of what?"

"Never mind," I said. "I'm so sorry for my little... umm... practical joke." I was attempting to dissemble, and doing a horrible job of it.

"I'm just kidding, Brian," he said, breaking into a broad smile.

"What?" I asked, really confused.

"Of course I'm in The Club. My preference is fucking a muscular ass, and getting a tough stud like you to moan like a bitch," he said, standing up.

"Jesus Christ," I said, both relieved and pissed off.

"I'm sorry, I really shouldn't have done that."

I was speechless.

"You do take it in the ass, I hope?" Mr. Mills asked.

"I do," I admitted, the shock to my system still recovering from his cruel prank. "But only a few times so far."

"Good," he said, pulling open his drawer and pulling out some lube. "Stand up, pull your pants down, and bend over my desk."

"Sir, I'm not sure I have enough time for that," I said, stubbornly remaining on my knees, because for the first time since discovering my love for cock, I suddenly wasn't in the mood.

He walked over to me, pulled his pants down, and revealed a long nine-inch cock. "Do you have time for this?"

"That's a very nice cock," I admitted, instantly mesmerized.

"I know," he said, and he slid it into my mouth.

My anger faded, my cock lust rose, and I began sucking his big, hard dick.

"Yeah, get it nice and wet and ready for your muscular ass," he said.

He was my second butt fucker to favourably mention my muscular ass just before using it. I'd always perceived faggots as being slim, scrawny twinks... thus that should be what other gay men were drawn to... but I was beginning to discover there must be a lot of men who wanted a strong, well-built man to bend over so they could pound him.

Mr. Mills pulled out and ordered, "Now present that ass to me."

"Yes, sir," I said, my reluctant mood now gone, and now wanting to feel his long, thin cock in my ass... and my cock for the millionth time struggling to break out of its steel cage. It was then I recalled I was wearing pantyhose. But hey, ¡no problemo! Shame no longer something I cared about, only wanting to feel that cock in my ass, I just pulled my pants down.

"Pantyhose and panties," he noted, a little surprised.

"And my clitty is in a cage," I pointed out, sounding pathetic, but like I said, I didn't care.

"Really?" he asked with a bit of astonishment as he lubed his long dick.

"My girlfriend likes me better that way," I explained as I pulled my pantyhose and panties down.

"I see," he said, as he got behind me. "You're just full of surprises."

"Tell me about it," I said, as I felt his wet cock head nestling between my ass cheeks.

"Do you like it in the ass?"

"I've only recently discovered my affinity for it," I said, my sounding really dumb to say that.

"I'm going to pound this muscular ass regularly from now on," he warned me, as he pushed forward, his hand resting on my back, and as his dick slid inside me.

"Oh yes," I moaned, his long cock not all that thick, but feeling damn good.

"Yes, such a tight, muscular ass," he groaned, as his cock continued traveling deeper and deeper inside me.

"Yes, fill my tight ass with your big cock," I moaned.

"I cancelled my regular Wednesday fuck for you," he said.

"Mmmmmm," I said, this school full of sex secrets, "another student?"

"Another teacher."

"I see," I moaned, and he was now balls deep in me.

"Yeah, she loves my cock," he said.

"A woman then," I said, for some reason this surprising me even more than my having a teacher's nine-inch cock in my ass.

"Yeah, Karen is a really nasty ass slut."

"Mrs. Pennyworth?" I asked, the woman under discussion in her fifties, quite large, massive tits, married, with eight kids (eight? Fuck!), and originally from England... her accent turned me on.

"Yeah, I usually dump a load in her ass every Wednesday," he said, as he began slowly fucking me. "She wasn't happy, but I couldn't miss exploring this opportunity."

"I'm happy you did."

"Yeah, this week I'll fuck her ass after school."

"Hot," I moaned, wondering what she'd sound like, dirty talking away in her ultra posh accent..

"Yeah, she's a nasty slut."

"So am I," I moaned grammatically, calling myself a slut in just my American accent.

"And so you are! Do you want to be my regular slut, Brian?" he asked, as he began fucking me faster.

"Yes, sir," I moaned. "I'm a good girl, a good cock sucker, and a good cum bucket. Isn't my pussy tight?"

"So very tight," he said as he fucked my ass.

"Yeah, I can either be your fucking football faggot, or your sexy submissive sissy slut," I offered, offering him two different versions of me.

"That was quite the alliteration elocution," he noted.

"It was?" I asked, not even certain of exactly what I'd said with his cock feeling so good... pre cum undoubtably oozing out of my long neglected clitty.

"Five years from now, do you want to be a man or a woman?" he asked from out of the blue.

That question really threw me! And I didn't actually know the answer. A cock sucker was still a man. I could be getting pegged all the time and still be a man. But getting ass fucked like I'd recently progressed to, and which was happening right now, was straying towards feminine realms. Wearing panties and pantyhose was even more feminine.

"I-I-I don't know," I stammered, not really having any good answer to that question.

"Well, while you examine that question," he said, "squeeze your ass cheeks tight together while I fuck you."

"Okay," I said, doing as he instructed, and his cock inside me began feeling even better.

"There you go," he said. "You either have a tight ass, or an amazing pussy, or both."

"Yes, fuck me, Mr. Mills, fuck my ass, fuck my pussy, breed me with your big cock," I began babbling, wanting to feel him cum inside me, as this simple new nuance of clenching my sphincter both enhanced my pleasure of the fucking, and it seemed, the pleasure he too received.

"Yes, do you want my load inside you, Brian?" he asked while he slammed into me.

"Yes, Mr. Mills, please breed me, come inside me, gape me, turn me into a bimbo fuck slut for you," I continued babbling slutty gibberish.

"Oh fuck," he groaned, depositing his big load in my ass, his cum now so deep inside me.

"Yes," I moaned, knowing from the exhilaration I felt that if I wasn't wearing that cage, I'd be shooting a sissy orgasm! And even as it was, my cock was throbbing against the confines of its restrictive cage.

"I think you're becoming more and more of a sissy slut who'll do anything for cock," he assessed as his load kept filling me. "A cum bucket whose greedy pussy is available to every cock."

"Yes, sir, you're likely correct," I agreed mindlessly, the pleasure of this sodomy, the nasty accuracy of his words, and the thrill of being a cum bucket moulding me into a most agreeable bimbo.

He pulled out, slapped my ass and said, "You should likely get to class."

"Thanks for fucking me, Mr. Mills," I said, as I pulled up my panties and Mom's pantyhose.

"A pleasure. I'll be unloading into that pussy a lot."

"I hope so," I said, feeling his cum leaking into my panties as I pulled my pants on.

"Oh, that's a guarantee," he said. "You're a great fuck."

"Thank you," I said, flattered by the compliment.

He wrote me a note, and I arrived late to another class.

Sitting in class with a load of cum leaking out of my ass was weird. Surreal. Slutty. Distracting. And a real turn-on!

The rest of the day passed without any further action or drama, other than my being razzed by a couple of the guys for going to meet Rose's parents that night. Pussy whipped much?

I got home, thought about watching another sissy video... there were only two left... but figured I should shower before Rose picked me up... since I did have dried cum both inside and immediately outside of my asshole.

I showered. Decided to go commando like Jennifer Aniston in that epic Friends episode. (Except that I doubted she was wearing a cage.) Snuck into to Mom's room and filched my third pair of her pantyhose in under twenty-four hours... put them on, with dress pants over them... added a dress shirt, tie and a blazer, and I'd just finished brushing my teeth when Rose arrived.

"Looking sharp," Rose smiled, as I got into her car.

"You look amazing," I said, admiring her in a gold dress and mocha nylons.

"Ready to meet my parents?" she asked as she drove.

"As ready as I'll ever be," I said awkwardly.

"So, if anyone asks, and they will," she coached. "You're my boyfriend."

"And I really am your boyfriend, right?" I asked, the way she'd said that making me feel a little less certain, and thus instantly insecure.

"Of course you are," she said, resting her right hand on my leg. "It's just that my family can be a little overbearing."

"Which explains where you got it from," I joked.

"Hey," she objected mildly. Flirtatiously even.

"Just saying," I smiled, putting my hand on hers... sharing an intimate moment.

"Sirrah, is this vile accusation because I pegged you, or because I caged you?" she asked, employing an outdated but posh English accent (think Shakespearean).

"Or transformed me into a cock sucking bottom?" I asked, raising a posh eyebrow at her. It was crazy how such conversations between us had now become normal.

"You chose to indulge in those activities," she pointed out.

"Well," I said, pondering this point, and thinking of how many cocks I'd sucked of my own accord, and how I'd begun willingly taking it in the ass, but only after she'd pegged me, and then Alyssa had fucked me at Rose's urging. "I guess I'm taking the ball and running with it, but you had a lot of influence over the initial stages."

"All I did was awaken the inner sissy cock sucking bottom boi you were born to be," she said.

"Then all I can say to that is thanks," I said, her appraising words feeling both humiliating that she'd felt that was who I was from the very beginning, and yet relief-giving because she totally accepted me... loved me even... for who I'd become.

"I meant that as a compliment," she said, placing her hand on top of mine (on her leg) and giving it a squeeze. "I'll only date a man who's comfortable with his full range of sexuality."

"It was a bit tough at first, but I've been learning to accept it," I laughed.

"Yes, you have. And I'll continue to guide you throughout your entire journey," she promised.

"I'll need you to."

"So how many of the videos have you watched on your newest USB?" she asked, changing the subject.

"Five of the seven," I said. "These ones are a little more intense."

"Yes, it was time to enhance your training."

"They're definitely interesting."

Yeah, and they're also hot as fuck."

"Agreed," I said. Then after a pause, "What exactly am I training for?"

"To discover your full and true sexual self."

"I don't even know what that means," I worried, as I pondered my caged cock and my recent lust for being ass fucked.

"It will all make sense in due course."

I sighed.

"Don't you trust me?"

"I do."

"But?"

"But I feel I'm losing myself even while I'm discovering myself."

"I can easily understand that."

"You can?"

"Yes, it's always scary to learn undisputable things about yourself you didn't know were there, especially if because of them you'll be judged negatively by some people, just like you used to judge nerdy people negatively," Rose said.

"I guess," I said. What she was saying was a lot.

"It's best if you don't overanalyze all of this and just take things as they come. So for now, let's just enjoy tonight," she said. "And tonight you're my man."

"I'll always be your man," I emphasized.

She gave a slight nod as she pulled into the Walton Hotel.

"This is where the birthday party is?" I asked. I'd thought all this time I'd be visiting her parents' home in suburbia somewhere. You know, the five of us sitting around a middle class dining room table, with the fanciest accoutrements being the silverware.

"Yes, that's right," she replied as if it were no big deal, as she pulled up to the front of the hotel.

I couldn't believe it! This was the hotel of hotels. The place where all the celebrities stayed. The place where royalty stayed when they deigned to grace our continent with their presence. It was the epitome of the rich and famous!

The moment she stopped the car, our doors were opened by two doormen.

"Good evening, Ms. Parker," one of them greeted.

"Hi, Charles," Rose said, kissing his cheek... which although it was a harmless gesture, still made me slightly jealous.

"And how are you this evening, Ms. Parker?" Charles enquired solicitously.

"I happen to be exquisite," Rose replied grandly. "This handsome gentleman is my beau Brian."

"I wish you the best of evenings, Brian," Charles said warmly.

"Hi there," I replied, a little less warmly and not at all grandly.

Rose took my hand and led me into a hotel I'd only ever driven past.

"So how often to you come here?" I asked, since at least one of the doormen knew her, and she him.

"Quite often," she said, and then added yet another shock, and for once not a sexual one, "Daddy owns it."

"Your father owns the Walton Hotel?!" I asked, even though she'd just said so... yet I was really only saying it out loud to process it, and also to make it obvious how shocked I was.

"Yeah, for about fifteen years now," she said, like it wasn't a huge deal.

"Wow!" I said, more than a little overwhelmed, as she led me through an amazing lobby that turned back time to the eighteen hundreds... its Renaissance Revival architecture making it appear that we'd just stepped into London's Mayfair District in the mid-Victorian era.

"Just be cool," Rose said, squeezing my hand.

"Yeah, that's me," I joked, even though pre-Rose that had really been me.

During the next thirty minutes I met a couple dozen of Rose's relatives, got my ass squeezed by my first real cock in my ass gal (the shemale Alyssa), and was introduced to another dozen rich people and a couple dozen celebrities (movie directors, actors and actresses, a couple of politicians, and my favourite author)... the entire experience was surreal.

I also encountered Elmer and Eugene. Of course Eugene would be here... it was his Mom's fiftieth birthday too.

Elmer grinned at me smugly... which made me blush and look the other way.

Eugene hardly gave me a second look, as he spoke with a stunning brunette with an exotic look to her. Eastern European, perhaps? Oddly, that made me feel jealous... which made me feel pathetic... which made me annoyed with myself.

Then there was this crazy entrance. An entrance so grand I felt I was attending a red-carpet Hollywood awards event.

First, there appeared the Governor of the state, Daphne Greene, the hottest politician ever and a potential future president, who introduced Rose's mother to the throng, although she was someone "whose name I shan't bother to mention, since she requires no introduction."

Second, there was Chris De Burgh, the actual Chris De Burgh (I recognized him because Lady in Red was my favourite song), singing the actual Lady in Red.

Third, and even topping the first two crazy surprises, there was Rose's mother. Whose surname wasn't Parker. No, not for a heartbeat. It was Dixon. Rose's actual mother was the actual hugely famous, gorgeous and popular actress and model Sarah Dixon. Actually! No fucking way!

Rose squeezed my hand and whispered in my ear, "Have I ever happened to mention my Mom is super famous?"

"No you didn't," I said, almost speechless, as Rose's hot Mom, whom I'd jerked off to many, many times before I ever met Rose, sauntered through an archway and into view, then down the middle of the red-carpeted (of course it was) aisle like the movie star she was. She waved to some people, hugged a few others, and then... walked directly towards us!

"Be cool," Rose reminded me.

"Yeah, that's me all over right now," I laughed awkwardly, as I stared at my dream MILF striding directly towards me. Oh yes, and towards Rose too, which was likely more her intention.

"You may resume breathing now," she prompted me, squeezing my hand.

"Rose, my lovely girl," Sarah Dixon greeted, hugging Rose. Then after a moment, she turned to me and said, "And you must be Brian."

"H-h-hi, Mrs. D-D-Dixon," I stammered, stunned she already knew my name.

"You're a cute one, just like my Rosie said you were."

"T-t-thanks," I stammered again, totally overwhelmed.

"We'll chat some more later," she said to us both, before wafting away to continue meeting and greeting people, beginning with her son... Eugene. Yes, Eugene, the nerd I'd bullied for years, but now had submitted to as my sexual Master! And Eugene's Mom was one of the hottest women in the universe! How was that even possible? And why was he attending a public school, when he could obviously be hobnobbing around some prestigious private school? And why didn't he tell anyone his mother was the Sarah Dixon? I had so many questions... yet no answers... just mind-numbing bewilderment.

"Sarah Dixon is your mother?" I asked, not as a question, but as a 'What the fuck'.

"Yeah," she said, although she didn't appear as enamored with her as I was.

"Jesus Christ!" I said.

"She isn't what she appears to be," she said.

"What do you mean?" I asked, noticing for the first time a deep sadness in Rose's eyes.

"Nothing," she said, turning away from me. And then I almost wasn't able to hear her mumble softly, "You'll see."

"Rose, you know I'm always here for you," I said earnestly but just as softly, not wishing to make a scene, but sensing she harbored some major resentment towards her mother. I pulled her back to me.

"I do know, and that's sweet of you," she said, just as her Dad arrived.

"You must be Brian," he said, his voice deeper than I would have imagined.

"Hi, Mr. Parker," I said, shaking his hand.

We chatted for a couple minutes before he finished, "Now treat my girl right."

"I certainly will, sir," I said, having long ago decided I'd do anything for her, and had proved it over and over again.

"And always do whatever she tells you to," he added as a parting shot, before striding away.

"That's very good advice," Rose said, as I tried to process his final words and the way he'd said them.

"That was weird, right?" I asked. This time I didn't see any sign of resentment. She obviously loved her father dearly.

She shrugged as a waiter came around with champagne, followed by a waitress with the fanciest hors d'oeuvres I'd ever seen, "Like I said, it's very good advice."

"I think I'm already living that advice," I joked, as I ate something very fishy. It looked a lot better than it tasted, and I quickly washed it down with half of the champagne in my flute... which made me gag a little, since I hated the bubbles in champagne.

"And don't forget it," she said. And then she turned and walked briskly away from me.

I stood pretty much in place for a couple minutes looking around, trying to get up the nerve to go and speak with at least one of the many celebrities nearby, when a pretty hotel staffer in a uniform walked up to me and asked, "Brian?"

"Yes, that's me."

"Your presence is required in room 1502."

"Excuse me?" I asked, but she simply walked away.

I looked around the room and couldn't see Rose anywhere. Was the summons from her? And why had the woman told me my presence was 'required', instead of the usual 'requested'?

I headed out of the ballroom, went into an elevator which was conveniently open, and pressed 15. As usual during the past couple of weeks, I was curious to know what I was getting myself into.... But as usual I was going along blindly... and also as usual, I was already excited about whatever mysterious event was about to occur.

I reached the floor, and saw there were only two rooms... or rather they must have been incredibly large suites... each almost half the size of a city block... on this level: 1501 and 1502.

I took a deep breath and knocked on the door, having no idea who was on the other side of it. Likely Rose... or perhaps Eugene.

The door was opened, and it wasn't Rose... and it wasn't Eugene... it was Elmer.

"Come on in, cock sucker."

"I really can't leave Rose downstairs by herself," I objected, pretending I didn't want to suck his cock again.

"Just do as you're told and get in here, bottom bitch," Eugene's voice called out.

I sighed... as Elmer smirked... and I walked inside to see Eugene sitting on the edge of a huge bed. Kneeling on the carpet in front of him was the same beautiful brunette as before, but now she was totally naked except for a black bra and pantyhose, and instead of standing around chatting with him, she was kneeling in front of him and bobbing on his cock.

"Go and join her," Elmer ordered.

"Eugene, I really need to get back downstairs," I objected, even as my mouth began watering and I felt some odd envy directed at the hot girl bobbing on his cock. I wanted that cock for myself!

"What you need is to get over here and suck my cock," Eugene said. "I promised Anastasia here she could watch a man getting spit-roasted, and she's dying to see it."

"Spit roasted?" I asked, even though of course I knew what it meant, and I'd been wondering how soon I'd get the chance to experience what it would be like to suck one cock while taking another one in the ass.

"Don't pretend you don't know what spit-roasting is," Eugene said, as the brunette was still slowly bobbing on his cock.

"Now get on your knees, faggot," Elmer ordered. "We don't have all night."

"Yes, at some point my sister will start wondering where you are," Eugene said.

The brunette backed off the big cock, looked at me and gasped, "This is Rose's boyfriend?"

"Yeah," Eugene said, and my face went as beet red as I imagine was possible.

"Get over here and suck this cock," the hot brunette ordered me in a Russian accent.

My submissive nature and my hunger for cock taking over, I walked over and dropped to my knees beside this hot woman and that big dick.

"Shit," she said, as she pushed on the back of my head, and I opened my mouth and took Eugene's cock into my mouth.

Wanting to impress her, which was ridiculous, and loving Eugene's cock so much, I began to bob.

"Fucking hot," she said, her accent so fucking sexy.

"There are many faggots here in America," Elmer said, sounding like the voiceover for a travelogue.

"Yeah, the bigger the man, the more likely he is to be a cock sucker," Eugene said.

"At least that's true at our high school," Elmer qualified.

"Come and fuck me, Elmer," Anastasia ordered.

"As you wish," Elmer said, as I sucked Eugene's cock.

A minute later, I was listening to the Russian girl moaning while she was being fucked right next to me.

"Oh yeah, fuck me, fuck me, fuck me," the Russian said, and I wished I could watch this hot Russian taking Elmer's big cock.

"Slow down, cock sucker," Eugene said. "You're just supposed to be keeping me hard for that ass of yours."

I obeyed, as the girl moaned and laughed, "And you say he football player?"

"Yeah, he's a star," Elmer said.

"And he likes girls?" she asked.

"Yeah," Eugene said. "Although I think he prefers cock to girls these days, don't you, cum bucket?"

It was obvious Eugene was relishing this chance to humiliate me in front of this woman, as he pulled his cock out of my mouth and I sheepishly replied, "Yes."

"Yes what, cock sucker?" Eugene asked, slapping my face with his hard cock.

"I prefer cock," I answered, sounding pathetic, and yet all I wanted was his cock back in my mouth as I glanced over to watch Elmer pounding the Russian beauty from behind.

"What do you prefer it over?" he asked, cock-slapping my face again, as humiliation continued to compound humiliation. Yet my lust for cock and cum overrode my dignity and any sense of shame.

I responded, knowing exactly what he wanted me to say, "Yes Master, I prefer big cock over pussy."

"He's calling you Master now?" asked Elmer. "Since when?"

"Since this afternoon," Eugene replied airily. Then redirecting his attention to me he queried, "So if my sister was here and she asked you to fuck her, you'd choose to suck my cock instead?" Eugene asked, tracing my lips with his cock head.

I didn't want to admit it... I didn't... not to him, not in front of Elmer, certainly not in front of this Russian stranger... and not even to myself... yet the truth was the truth, and even while my cheeks burned the darkest shade of red ever, I admitted, "I'd choose your cock, Master."

"Holy shit," Anastasia moaned.

"Louder!" Eugene demanded, accompanied by another slap of his hard cock.

"I'd choose to suck your cock over fucking your sister or any other girl," I declared, my shame fading as my lust and acceptance grew.

"So you would rather suck his cock than fuck me?" the Russian hottie asked.

I looked at her pretty face, her amazing body, and yet said, "Yes, I'd rather suck Eugene's massive dick."

"And mine too?" Elmer asked.

"Yes, and yours too," I admitted reluctantly, sounding like an even bigger faggot in front of this Russian goddess. Yet my lust for cock, and my experience of having already been sodomized in front of Rose, made these humiliations torturous, and yet they were impediments I persevered through for the cock and cum I constantly craved.

"Spit-roast the sexy fuck toy," Anastasia said.

"You heard her, faggot," Eugene said. "Get undressed."

"Um, I really should get back to your Mom's party," I said, not wanting them to see I was wearing pantyhose and was caged. Again, I'd set out from home expecting to attend a reasonably formal dinner party, and not anything where I'd be removing my clothing!

"Did I ask for your opinion, fuck toy?" Eugene asked with a sneer, slapping my face with his cock again, clearly showcasing his dominance over me in front of the pretty woman.

"No," I sheepishly said.

"Then get out of your pants," Elmer ordered as he pulled out of the hot brunette. His obvious preference for shoving his cock into me instead of her had me inwardly shaking my head in wonderment.

I stood up, unbuttoned my dress pants, and pulled them down.

"He's wearing pantyhose," Elmer said, roaring with laughter.

"Why he in pantyhose?" Anastasia asked.

"He wants to be a girl," Eugene said, examining me and pointing at my caged cock. "Is that my sister's doing?"

"The cage, yes," I answered.

"Not the pantyhose?" he asked.

"No, that's my doing," I admitted, wondering if there was a darker shade of red I could blush than I already was.

"Wow, you really are a girl in a man's body," Eugene chortled, as Elmer went behind me and pulled my pantyhose down to my knees.

I didn't say anything, just stood there in shame.

"On all fours, sissy slut," Elmer ordered, winking at Anastasia.

I silently obeyed.

"I get his ass," Eugene claimed.

"I know, I know," Elmer agreed with a sight sigh.

The two swapped positions so Elmer's big cock was in front of my face, while I was on all fours like a dog... or a bitch in heat.

"Spit-roast the bitch," the Russian said. Yes, she too spotted the resemblance.

"Do you want to get spit-roasted, faggot?" Eugene asked as he positioned his cock at my ass.

"Yes Master," I whispered barely audibly, so ashamed at this hot but rather sadistic witness observing my first double dick adventure.

"Say it with pride, faggot," Eugene ordered, slapping my ass with his cock.

"Yes, I want to be spit-roasted by your two big nerd cocks," I declared, wanting to feel those cocks in my mouth and ass... pushing my shame away, which was there because I was about to be spit-roasted by two nerds... in front of a beautiful Russian... while my girlfriend was downstairs. Or somewhere; actually, I had no idea where she was or what she was doing. Was her mother making her do something unpleasant? I hadn't imagined that resentment I'd seen on her face.

"Louder, beg for it," Eugene ordered as both cocks slapped me.

I knew they were trying to humiliate me even further... to show off their power over a muscular jock... to impress this ridiculously hot Russian. Yet like always when a cock was in front of me, pride flew out the window, and my lust for cock took charge. So they wanted to humiliate me? Bring it on! I happily responded to Eugene's demand, "Please! Shove those big cocks into my mouth and my pussy, and use me like the sissy slut I am."

"Shit, he calls it a pussy," Elmer said, emitting a large roar of laughter.

"Yeah, he does," Eugene smirked.

"Just fuck the faggot!" Anastasia demanded, and I glanced over to see she was now sitting on the edge of the bed, her legs spread, and the entire neck of a wine bottle jammed up her pussy.

"You heard the lady," Eugene said, and he slid his cock into my tight pussy.

"Ohhhhhhh, fuck," I whimpered, sounding completely feminine as my pussy was filled.

"Shut up, slut," Elmer said, as he slid his cock in my mouth to indeed shut me up.

Suddenly I had two cocks inside me!

Suddenly I was actually being spit-roasted!

It felt so good... two cocks sliding in and out of me at once.

"Shit, he's the biggest faggot of all our jock cum buckets," Elmer crowed.

"Yeah, he's a complete cock craving cum slut," Eugene agreed, slowly fucking me from behind.

His words should have been humiliating, and yet why? That's exactly what I'd become. What with Rose's guidance I'd been training to become. A complete cock craving cum slut willing to do almost if not anything for a cock in my mouth, or a cock in my pussy, and in either case cum spewing into me. To signal to them I agreed with the sentiment, I moaned on Elmer's cock.

"He just moaned his agreement," Elmer chuckled, his laugh making the cock in my mouth vibrate subtly.

"Yeah, once there's a cock anywhere near him, he becomes a complete cock hound," Eugene added.

"Fuck him, fuck him hard," Anastasia moaned, sounding like she was really getting off at the sight of me getting fucked in both ends.

"Do you want to get fucked harder, Brian?" Eugene asked.

Elmer pulled his big cock out of my mouth so I could answer affirmatively, wanting to really get pounded, "Yes Master, I want you to fuck the shit out of me while this hot woman watches."

"And to face fuck you?" Elmer added, and I got my face slapped again, by his cock this time.

"Yes please, face fuck me and use my mouth for your pleasure, the harder and deeper the better," I responded, wanting his cock back in my mouth, wanting to show this Russian devushka what a great cock sucker I was.

"Shit," Elmer said, as he slid his cock back into my mouth.

Eugene resumed fucking me, faster now, and I just stabilised myself on all fours while I was fucked in both ends.

"Oh yeah, fuuuck him, fuuck him hard," the Russian said, her hot accent and moans enhancing this moment that had already been making my cock throb in its cage.

"Are you enjoying this?" Eugene asked.

I could only moan in response, loving the thrill of these two cocks sliding in and out of me!

But I realized when Anastasia answered, he hadn't asked me. "Yes, it so hot, honey."

"He likes it too," Elmer laughed again, really amused by how pathetic a faggot I was for his and Eugene's cocks.

It was lucky I was wearing the cage, or I'm sure I would have embarrassed myself all over the floor from the pleasure of this spit-roasting. The thrill of taking two cocks at once was yet another new sexual high.

After a couple minutes, Anastasia and me both moaning throughout, Eugene ordered, "Now you do the work. Ride and suck, slut!"

I'd seen this in the movies (no, not the Bijou downtown, silly), so I understood exactly what he expected. I began bouncing back to take Eugene's entire cock in my ass/pussy, then leaning way forward to take Elmer's cock deep into my throat. At first it was rather awkward, and I struggled to rock back and forth smoothly, but after a dozen or so cycles, I found my rhythm.

"Oh fuck, that's so hot," Anastasia moaned, as now smoothly, I went back and forth, taking one big cock in my pussy and then the other in my throat.

I moaned on Elmer's cock, loving to suck his cock, loving to take Eugene's in my pussy, and loving to have Anastasia getting off from watching. I couldn't explain why, but knowing she was paying such close attention enhanced my wild euphoria, and I knew pre-cum must be oozing out of my clitty.

"I'm going to come soon," Eugene declared.

"Come inside the faggot's asshole," Anastasia urged him delightedly, sounding like she was fucking herself frantically with that bottle.

Elmer pulled out of my mouth and I mindlessly begged Eugene, "Yes please, fill my pussy with your cum after you've pounded my cunt!"

"Oh, fuck," Anastasia moaned loudly as she came.

"Fuuuuuuuck," Eugene grunted, and spewed his load into me.

"Yessssss," I moaned from the feeling of cum filling my ass.

"Open wide," Elmer ordered, and he slid his cock back in my mouth and face fucked me really roughly.

I moaned on his cock, feeling my ass full of cum, and then a minute or two later, I felt Elmer's load erupt in my mouth and his jizz glide down my throat.

"Swallow it all, jock cock sucker," Elmer grunted.

I had no choice as he pumped his cock in and out of me, although of course I would have swallowed the load willingly, regardless. My addiction to cum was uncontrollable.

Two minutes later, cum was leaking out of my asshole, and I was pulling up my pantyhose.

"You'd better get back to my sister," Eugene said, as he got dressed too.

"Yeah," I said sheepishly, wondering what I could possibly tell Rose about where I'd been.

"Yeah, go and find Rose while her brother's cum leaks out of your ass," Elmer laughed.

I didn't say anything... there was nothing to say.

I headed out, and Anastasia waved me a cheery goodbye, "Bye, faggot." Cheery with a sadistic edge to it.

"Bye, ma'am," I said sheepishly as I left the room... aware that a month ago I would have fucked that bitch good.

I pressed the button and waited for the elevator, while indeed feeling cum leaking out of my pussy and into my pantyhose.

I reached the main floor and wondered how long I'd been gone. Twenty minutes, perhaps. No more than thirty, I figured.

I went back into the ballroom and saw Rose chatting with Alyssa... who possessed the first flesh and blood cock ever to fuck my ass/pussy.

I sheepishly walked over to them after grabbing some champagne, and said to Rose, "There you are."

"Hey, sorry, I had a long visit with Mom," she said.

"Hey, didja miss me?" Alyssa asked.

"Maybe," I shrugged, trying to act coy.

"Sure, Little Miss Maybe, Maybe Not," she laughed. "I bet you'd meet me in the bathroom right now if I offered you my dick."

"You can go if you want to," Rose said.

"No, I should stay with you," I said, trying to be the good boyfriend just after not being a good boyfriend.

"Sweet," Rose said, kissing my cheek.

"Gross," Alyssa said.

"Maybe later," Rose said.

"Maybe," Alyssa said, leaving us alone.

"So... Mom likes you," Rose said.

"Does she?" I asked, flattered that one of my most prominent jerk off fantasies liked me.

"Yeah, so be careful; she likes her men young."

I smiled, "I'm not sure I'd be able to do much, no matter how hard I tried," I joked about the cage while I pondered her words.

"No, I guess not," she smiled. "How are you doing with it?"

"It's definitely frustrating."

"Yeah, I know. But like I explained on the weekend, it's all about learning to control your orgasms. Through denying yourself, you'll build yourself up to exploding with some of the most intense orgasms imaginable."

"I sure hope so," I said. "But so far it just feels like I'm giving myself endless blue balls."

"Oh, but wait until Friday night," she promised.

"I realize it's already Wednesday night, but that still seems an eternity away," I said, feeling some more cum leaking out of my ass.

"All good things come to those who wait," she quoted.

"Then I'm expecting an epic night on Friday," I said, also wondering about Saturday's initiation.

"Oh, it will be," she said in her seductive way that could melt the North Pole, especially these days.

"That alone would make me rise if I could," I said.

"Mmmmmmmm," she smiled.

We sat down for dinner with Eugene and Elmer, along with two of Rose and Eugene's cousins. I was nervous throughout the entire dinner... Eugene's cum creating a small pool in my pantyhose... and I worried he might out me. Rose knew I'd sucked her brother's cock... Christ, she'd set it up at least two of those times... but I doubt she knew how regularly I was now sucking his cock, or that I'd just been spit-roasted by him and Elmer.

Luckily, nothing was said about any of that.

After some speeches, and some birthday gifts I'm pretty sure were worth more than my parents' house, there was dancing.

I danced with Rose, and then with Rose's Mom....

She whispered, halfway through the song after a few generic questions about my school and family, "You're a handsome young man."

"Thank you, Miss Dixon," I said, her perfume drawing me in.

"It's Sarah," she corrected me.

"Right, thank you, Sarah," I said nervously.

"So how long have you been fucking my daughter?" she asked after about twenty seconds of just slow dancing.

"P-p-pardon?" I stammered.

"You have fucked my daughter, I'm assuming."

"Um... I... well..." I struggled to find some words.

On the dark dance floor, she purred as her hand went to my caged cock, "I'll take that as a yeeeesss."

She looked at me in confusion.

I still didn't know what to say.

We continued dancing for another speechless minute, my cheeks burning red the entire time because first, one of the most beautiful and famous celebrities in the world had just hit on me, and then second, she'd felt with her own hand that I was wearing a cage. Finally I said, "Rose makes me wear it."

"I see," she said, since she'd assuredly been trying to process why I was caged.

The song ended, and she said, "It was a pleasure to meet you, Brian."

"You too, Sarah," I said, feeling so ashamed at being outed that way to someone like Sarah Dixon.

I saw Rose dancing with her Dad, and I headed off to get some more champagne, hopefully from a bottle that had been open long enough to go flat. Success! Then while I was sipping my non-bubbly, Alyssa walked up behind me and said into my ear from about two inches away, "Need that pussy fucked?"

"Jesus!" I said; she'd startled me.

"Is that a yes?"

"I think I'm okay," I said, even though the chance to get ass fucked again by Alyssa was very appealing.

"Guys bathroom on the second floor," she ordered. "Five minutes."

Before I could respond one way or the other, she was gone.

I sighed.

I was literally becoming a fuck toy addiction for everybody who knew my secret... a crowd that continued to grow. But of course, that addiction went both ways.

So I finished my drink and headed to the bathroom.

At the entrance was a Closed for Cleaning sign, and I assumed that was just Alyssa's way of giving us the privacy we'd need.

I walked inside, and she was already there... and so was Sarah Dixon!... who was on her knees sucking Alyssa's cock.

I just stood there.

Frozen.

"Hey slut, come join Sarah and me," Alyssa called me over.

I couldn't believe what I was witnessing... after all I'd experienced... everything I'd become... this tableau was somehow the most shocking thing I'd encountered yet!

I walked over in a daze, and dropped down beside one of the most famous women in the world... who was also my girlfriend's mother.

"I hear you like cock," she said offhandedly, after letting Alyssa's cock slip out of her mouth so she could speak. She was a master at setting atmospheres at the drop of a hat, and this one was casual intimacy... just two chums meeting next to a cock. Ah yes, it was a shemale's cock, but that was a mere detail.

"Yes ma'am, I do," I said, as she pointed the cock invitingly at me.

"Then go ahead, I want to see you suck Alyssa's big cock," the mother of my girlfriend said. It was an order, but we were still chums.

I couldn't believe this was happening... but nevertheless, I leaned forward and took Alyssa's cock between my lips.

"So hot," Sarah purred, as she watched me slowly bobbing on a shemale's cock.

"Show Sarah how much you love my cock, slut," Alyssa ordered me. Not at all chums in her case. For now, this was Mistress Alyssa I was servicing. Even though she was the one of my two companions who wasn't world famous.

I moaned on her cock and began bobbing faster, wishing to impress the Sarah Dixon.

"Shit, he really knows his way around a dick, doesn't he?" Sarah said, sounding impressed.

"You should hear him moan while I'm pounding his ass," Alyssa bragged about me.

"Really? I'd love to see that," Sarah said.

"Okay slut, do you want to show your girlfriend's Mom how much you love getting fucked?" Alyssa asked. She pushed my head back, and her cock slid out of my mouth.

I looked at the hot actress and offered, "I'm so sorry!"

"Sorry my ass! Sorry for what? I'm proud to see my daughter following in my footsteps," she tossed back.

"Pardon me?" I asked, totally blown away as Alyssa pulled me to my feet and manhandled me over to the counter.

"Yeah, taking strong men and turning them into submissive playthings is something I've loved doing throughout my entire career!" she revealed.

"Really?" I said, as I felt Alyssa pulling my pants down.

"Pantyhose?" Alyssa scoffed.

"Rose does love them," Sarah said, although I noticed she wasn't wearing any.

"Actually, she didn't make me wear these," I clarified for some reason, as Alyssa pulled them down.

"No?" Sarah asked.

"No, I've just always liked them," I said. "I even remember you wearing them without heels during that dance number in Rock the Boat."

"Oh yeah," she nodded. "I remember that. But I've never really liked them, myself."

"Too bad," I said, as I felt Alyssa pressing her cock against my ass, "they really bring out our legs."

"Who else has fucked you recently?" Alyssa asked.

"W-w-what?" I stammered.

"Your hole is still gaped, and there's cum leaking out of it," she pointed out, and Sarah came up behind me and looked too.

"Yeah, it was someone with a pretty big cock," Sarah added, as my shame compounded shame compounded shame!

"Who was it?" Alyssa asked. "It was obviously quite recently."

"Have you already been ass fucked at my party?" Sarah asked.

"Yes," I whispered, so embarrassed.

"By whom?"

"You don't want to know."

"I think I do."

"You really doooooooon't!!" I said, as Alyssa slid her cock into my gaped and cum-lubricated hole.

"Tell me," Sarah said, as she reached up and tugged my ear... hard!

"Ohhhhhhhh," I moaned, as Alyssa began fucking me... hard!

"Tell her, slut," Alyssa ordered, really slamming into me.

"Euuuuuuu-gene," I moaned.

"My son Eugene?" the celebrity gasped.

"Yeeeeeeeah," I admitted, the pleasure of getting ass fucked apparently having the same effect as truth serum.

"No way," Sarah said, looking genuinely surprised. "But he's a nerd!"

"That's true. But he has a big dick, and he uses me for his jock bitch," I added details, for reasons I didn't even know.

"Shit! Well good for Eugene," Alyssa said, as astonished by my revelation as his mother was.

"I'm his cock sucking, bottom taking cum bucket," I continued degrading myself, unable to help it, while my cock desperately struggled to break free from its restrictive cage.

"Yes, good for him," Sarah agreed, very impressed.

"Yeah, he has a few cock faggots he allows to suck him," I added.

"But he doesn't fuck them?" Sarah asked.

"I don't know about that, but maybe," I said, "tonight was the first time he's fucked me," as Alyssa kept pounding my pussy.

"So you're dating my daughter, while you're sucking and getting fucked by my son?" Sarah said, doing very well at processing the ins and outs of this ridiculous farce.

"And by me, too," Alyssa added.

"Yes," I moaned, her ass fucking really feeling good.

"Wow," Sarah said.

"Yeah, who knew the nerdy Eugene was a stud?" Alyssa said.

"I thought he might be gay, but I never expected this," Sarah said.

"Oh, there's no way he's gay," I moaned.

"No?" Sarah asked.

"He was getting blown by someone named Anastasia before he and Elmer spit-roasted me," I continued, making me sound even more pathetic... outing myself to even more crimes against nature.

"Spit-roasted? You really are a faggot," Alyssa laughed.

"Anastasia?" Sarah said. "Good for him!"

"Last time I fucked Brian, he came without getting his dick touched," Alyssa added.

"A sissy orgasm," Sarah said. "Those are hot!"

"I'd be coming all over the place right now if your daughter hadn't caged me," I said, pleasure consuming me, my cock desperate to release several days of built up cum.

"I'll have a chat with her about the cage," Sarah said, as she came up beside me, bent over and said, "Now come and fuck my ass, Alyssa."

"Yes, Mistress," Alyssa said, hearing that term surprising me, as she pulled out of my ass.

"And you, my musclebound Nancy boy, get under me and eat my pussy," Sarah ordered.

"But you're my girlfriend's Mom," I objected as I watched Alyssa move behind Sarah Dixon.

"That exclusivity marched right out the door when you blew her brother," Sarah said. "You belong to the whole family now, so I'll need to tell my husband you're available. Now get the fuck between my legs!"

"Yes, Mistress," I obeyed, loving to use that word, as I got down on the floor, awkwardly crawled under the counter, spun around and stared at my girlfriend's Mom's pussy.

"Get licking," she ordered, and I leaned forward and began licking... feeling a bit guilty to be licking Rose's Mom's pussy... which somehow felt wrong, even though I'd already sucked her son's cock on multiple occasions, and had just been sodomized by him. Of course Rose had set up my first time sucking Eugene, and again last Saturday morning, so she obviously approved of his taking liberties with me... but would she approve of this? There was that resentment I'd seen in her eyes earlier, and her vague warning, so maybe not.

"Oh yes, fuck me, fuck me with that big cock," Sarah moaned, and I licked her pussy while she got ass fucked.

"You love my big cock, don't you, my big shot ass slut?" Alyssa said, switching roles as she slammed into the MILF model... going from calling her Mistress to slut in under thirty seconds.

"Yes, I love your cock, baby," Sarah said. "And I also love your tongue, Brian my girlfriend's cuck, and my son's cock sucking bottom bitch."

"And your cunt licking slave," Alyssa added.

"I'll be your anything, Mistresses," I trothed mindlessly between licks.

"Mmmmmmmm," Sarah moaned, the double pleasure clearly making her feel really good.

For a couple of minutes there wasn't any talking... just licking... ass fucking... and moaning.

Then Sarah became verbal when her orgasm was imminent. "Harder, ream my asshole! Eat my cunt! Suck my clit! Finger bang me!"

There were so many orders, but I obeyed each of the latter three... attacking her clit with my lips and tongue, while sliding two fingers easily in and out of her very wet pussy.

"Fuuuuuuuck," she screamed a minute or two later as she came, her juices cascading out of her, then onto and down my face, as I pulled my fingers out and drank her sweet cunt champagne. With no bubbles!

Alyssa pulled out a minute later and ordered, "Cock sucker, come and get your load."

"Yes, Mistress," I said, snatching a brief moment for a little more cunt cum before I crawled out from between Sarah's legs and stared at Alyssa's big, hard cock.

"Suck it," she ordered.

Even though it had just been in my and Sarah's assholes, I mindlessly obeyed, and sucked the big cock into my willing mouth.

"Oh yeah, he's an ass to mouth cum bucket too," Alyssa said approvingly, as she face fucked me.

It didn't taste like shit... just a little bit tart... and it only lasted about a minute before she grunted, and I swallowed her creamy load.

"Save some of that cum for me, Nancy," Sarah said.

I backed off of the cock even while it was still spewing at me, and I tried to catch it without swallowing it. Unfortunately Alyssa stopped coming before Sarah could get into position for any.

But that didn't seem to trouble her. "Give me that load," Sarah ordered me, now leaning back against the counter.

I stood up, the big load still in my mouth, and approached my girlfriend's mother for the ultimate in wet kisses.

She leaned in and kissed me open mouthed, while I transferred the gooey, salty load to her. She sucked it in, broke the kiss, and swallowed. "Mmmmmmmm!!"

I stared at her.

"You're a keeper," she said, looking at me, caged, and with pantyhose around my ankles.

"Yeah, a real keeper," Alyssa added, although her tone was dripping with sarcasm.

"I mean it," Sarah said. "Once you're not caged, I plan to have that cock shooting inside me."

"You do?" I said.

"Mmm-hmmmm," she said, lowering her skirt from around her waist as she strolled out, still fully dressed. Except of course still commando.

"You should probably get back to the party, cum bucket and soon to be mother fucker," Alyssa said.

"Yeah," I said, pulling up my pantyhose again... something I'd done a lot of today.

"Pantyhose," she said, shaking her head. "I think God made a mistake when he made you."

I sighed.

"Just saying," she shrugged, as she too lowered her skirt and walked out.

I followed her a minute later and returned to the ballroom.

I danced with Rose, I had two more drinks, and ended up in yet another hotel room, where I got Rose off with my tongue... feeling so guilty that I'd eaten her mother just an hour earlier.

I wanted to tell her how I'd been spit-roasted by her brother and sodomized by Alyssa, had licked her mother and swapped cum with her... with her Dad probably looming on the horizon... but I didn't even know where to begin.

So I didn't tell her anything.

But I did get her off... and she promised to blow my mind on Friday, and because she'd had a few drinks too many, she sent me home in an Uber, after stressing to me I needed to finish watching the last two videos by Friday evening.

Of course I said I would... although not tonight... I was too tipsy and tired.

I collapsed onto my bed, still in my suit and pantyhose, my head foggy from all I'd learned and done today, and from the excessive alcohol.

In two days I'd get this cage removed and experience a big surprise from Rose. Since it would have to be an experience instead of an object.

In three days I'd take part in some sort of initiation ceremony or hazing or who knew what, resulting in my having joined a men's sex club.

In ten days I might get the chance to take part in a massive male sex orgy. And possibly learn who else on the football team was sucking cock... and of course they'd learn about me.

And all that... was crazy... and yet it was unlikely to be as crazy as everything that had transpired today.

I drifted off into slumber, still fully dressed, but completely exhausted.

THE END OF CHAPTER 11

 

Link: https://www.literotica.com/s/hypnosissy-11