Hypnosissy 08: Hot Shemale

HypnoSissy: Hot Shemale

Summary: Brian loses his anal virginity to a shemale with a big dick.

WARNING PLEASE READ:

-This is a hypnosis story with potentially influential subliminal messages within it.

-The story also describes hypnosis video scenes.

-So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to me: you've been warned.

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.

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

Note 4: This eighth story will make more sense if you first read the first seven. But in case you don't have time, or you've read them a while ago and need a refresher:

HypnoSissy 1: Becoming a Cocksucker

A cocky 18-year-old high school senior, Brian, tries to seduce a pretty college girl, Rose, but instead is seduced by her. Rose, after allowing him to go down on her a couple of times, gives him a USB with a dozen videos that she assigns him to watch (unknown to him they are hypno-sissy videos), and gradually he begins to get curious about sucking cock and eating cum. After watching all 12, Brian is summoned to Rose's college dorm and before the night is done, he sucks his first cock and swallows his first load of cum.

HypnoSissy 2: Becoming a Cum Slut

Brian, having had his first cock, is given by the beautiful, mysterious Rose a second set of videos to watch. Watching the second set, his hunger for cock builds, until he meets a stranger at lunchtime in a van, and then is taken to a gloryhole by Rose, where he gets to suck on five very different cocks.

HypnoSissy 3: Big Nerd's Cock

Brian spends the day after the gloryhole visit desperately trying to avoid the nerd he'd sucked there. Of course by now his hunger for cock and cum control his very being, so in the end he succumbs to the nerd, one he'd bullied for years. After sucking and swallowing the cum from this nerd's big cock, he learns a shocking secret... he's Rose's brother. The chapter ends with Brian receiving a new USB from Rose.

HypnoSissy 4: Cum Cravings

Brian watches four more training videos, each reinforcing the proposition that he's a cock sucker and his natural purpose is to serve. After four days, Rose picks him up to take him to a special sex party, where he serves six men and is given a circle jerk baptism (sprinkling, not immersion) before serving another man. After watching a few wild sex acts, he sucks one more cock for the road; he then gets a business card from a mysterious stranger who orders him to text him tomorrow. The chapter ends with Rose fucking him in the car, and deciding he's ready for the next step in his training.

HypnoSissy 5: Ecclesiastical Sucking

Brian goes to meet the mysterious stranger, who is a Minister in a very unorthodox church. Brian's job interview is to suck two cocks, which he aces easily. He then is trained in the art of cock sucking by the church's GILF secretary before he gets to fuck and come in her ass. The chapter ends with Rose inviting him over for some new videos.

HypnoSissy 6: Educated to be Pegged

Brian watches more hypno sissy videos, including some with shemales and focusing on anal sex... with the climactic conclusion being his getting pegged by Rose.

HypnoSissy 7: Glory Hole with Nerds

Brian is offered the opportunity to suck off eight nerds at a glory hole at an all nerds party, and after desperately tying to resist the temptation, he ends up going there and sucking eight cocks, fucking a gay nerd (not through the glory hole), and getting blown himself.

And now the next part of his training begins in HypnoSissy

HypnoSissy Ch. 08: Hot Shemale

I arrived at the Wilsons' party, which was indeed in full swing, I could hear the music from a block away, where I had to park.

I texted Camry: Sorry for the delay. I just parked.

I reached the house just as Camry responded: We're in the basement dancing.

I walked into the house and wasn't three steps in, when Wally, clearly well on his way to an alcohol-fueled blackout, accosted me with, "Dude, where the fuck have you been?"

"Dude yourself, it's not even midnight," I retorted.

"Sho?" he demanded, managing to slur a two-letter word.

"Sho, the cool guys don't show up until the party is in full swing," I teased.

"Yeah? Well you need to catch up," he said, handing me a beer.

I laughed, "I'm not sure I could catch up with you tonight if I drank with both fists until I fell over."

"Well try," he said, as we both downed our drinks. "Shit, I need to piss."

"And I need to find Camry," I said.

"Need an oil change?" he smirked, his crass way to describe fucking a woman... which made me laugh at myself, since that was a phrase I'd coined, and now I found it crass.

"Always," I said, continuing to play my decreasingly justified big man on campus role.

He headed one way, I headed the other.

I got a few high fives, my ass squeezed, and kissed by Julie, who I'd banged in her garage a few weeks ago during her 18th birthday party with her friends and family in the house, as I made my way through the party.

I'd forgotten how great it felt to be The Man... having gotten myself so domesticated by Rose. No one here would believe I'd just finished sucking eight cocks, one of them twice, and had also fucked the twink Sammy... since everyone here saw me as a stud football player destined for a full ride scholarship at a great college, probably followed by a lucrative career in the NFL. Most of the guys envied me, and most of the girls wanted to fuck me. I know it sounds crude, but that was the reality... high school is the greatest façade in the world... where reality doesn't even exist.

I reached the basement, which smelled like a mixture of sweat and pot, as I felt my phone vibrate (since it was still on vibrate from my glory hole session).

I stopped and checked it out.

It was from Rose: Eugene said you had a great time at the glory hole. That's great. And I have another treat for you.

I was about to respond, when she texted me again: Look up and to your right.

I did, and there she was. On the dance floor with Camry and the big-dicked girl whose name I couldn't remember. I waved to her.

She smiled.

I walked over, and wearing my public masculine persona, I kissed her.

She kissed me back, and for now, I was The Man again. I was the Brian of old. I said, breaking the kiss, "Great to see you."

She responded, "You too, sexy."

"Let's dance," the girl whose name I still didn't remember said to me... a compete knockout... even hotter in person than she'd been in the photos.

And for the next twenty minutes, as one song blurred into another, I was The Man. All three women danced dirty with me, all three rubbed my cock through my jeans, and all three of them even made out with me... thus making all the other girls in the room envious of them, and all the guys envious of me... and for a little while I forgot I was now primarily a cock sucker... and relived the glory of my high school persona.

Rose eventually whispered in my ear, "Let's go. We need to fuck."

"Yeah," I said, not overly profoundly... but it was an excellent caveman response.

She took my hand, and to my surprise said more broadly, "Let's go, ladies."

The other girl, who I'd finally remembered was named Alyssa (okay, I didn't remember, Camry had used her name at one point), took my other hand, and I strolled like royalty through the party with two of the hottest women imaginable on my arms... while Camry walked behind us... which I felt a little bad about, since she too qualified as one of the three hottest women around.

I sauntered past a couple of buddies who gave me looks of 'Way to go, man,' and then Wally asked, "Are you going to share the wealth?"

"Yes, I believe I will be..." I smiled in full, self-centred stud mode, "...be sharing these fine ladies with... each other."

"You bastard," he accused grimly. Except the latter word sounded more like "bash turd."

Rose briefly left me behind, walked up to Wally, grabbed his crotch, and gave him a squeeze and a look communicating how sincerely impressed she was with his dick size, and lingered to rub it while saying, "Sorry stud, you can't come."

She kept rubbing though, and while the room went silent and everybody watched, very soon he groaned and came in his pants. "Oh, I guess I was wrong... you just did! Well done." (That last bit wasn't at all sincere, of course, but it was wonderfully patronizing.)

She kissed his cheek in her best untouchable fashion, took my arm again, and led me and our other two girls through the crowd of teenagers, who were in awe of what they'd just witnessed.

"You bisshhh," Wally called out, angrily and drunkenly.

"Yep, that's me all right," she called back, not at all fazed by his insult, but embracing it.

Once we were outside, Rose asked me, "So boyfriend, are you ready for some real fun?"

"Uh, yeah," I said, recalling how Rose's idea of 'real' fun had led me into some wild encounters like sucking black cock, a house party filled with sex where I'd sucked lots of cock and was 'baptised' bukkake style, and just last night, her pegging me.

"You don't sound very eager," she appraised.

"I never know what to expect from you," I said.

"True, which is what you love about me," she said, kissing me.

"One of the many reasons," I said, melting at her touch.

"Let's go to my place," she said, as she walked over to an Uber already waiting for us.

So that's how I arrived at Rose's apartment with Camry and Alyssa, where I was almost guaranteed to experience at least one, but probably a few more firsts.

Rose poured wine for all of us, and as she sipped, Camry announced she was hungry. So I watched as Camry dropped to her knees, and Alyssa raised her tight dress to reveal her very impressive cock. Although Camry had sent me a picture of this fascinating organ, so I'd assumed she was a shemale, and having been conditioned from some of my earlier hypno-videos to admire shemales in all their feminine and masculine beauty, it was still pretty wild to be near to one in person... a hot woman, with a great body and a cock.

"Go over and join them," Rose instructed me, likely because I'd been watching with a bit of envy while Camry sucked that cock. I'd already sucked eight different cocks today and taken ten loads (two from Sammy and a second one from Eugene this evening, his first one this morning), but greedy guts me, I was craving even more.

Alyssa pulled her dress up and over her head while I went over to her. Her tits were big ones, and instead of joining Camry on the floor, I joined her still standing, so I could worship her amazing body by cupping her tits and sucking on her nipples.

"Mmmmmmm, that's it, suck my tits," Alyssa said, looking completely feminine in every way except for the big cock dangling between her legs, but she'd obviously begun life as a boy, since with her voice still quite masculine, it didn't match her exterior. Not that I'm complaining!

I sucked on one nipple and then the other, before I really needed to see that cock up close and personal.

"Suck on my balls, Rose's bitch," Alyssa ordered, surprising me.

Was I the bitch?

Or was Camry?

As Camry continued sucking on her dick, I assumed that meant I was the bitch, so I leaned in to suck her hairless balls. But meanwhile wondering if I should do that.

"Mmmmmm, you have quite the cute little bitch," Alyssa said, as I sucked a ball into my mouth while Camry still sucked her cock.

"He's coming along very well," Rose said.

"He?" Alyssa asked.

"He, she, it's all arbitrary," Rose responded airily, which got me a little rattled. What did she mean it was all arbitrary? She'd previously made it clear I was still a man... and her man. Yes, she'd convinced me to suck a lot of cock and to explore my feminine side, but I was still basically a guy. Wasn't I?

"You know where she's going to end up," Alyssa portended vaguely, as I sucked on her other ball.

"I know what I want from him," Rose said, my champion still referring to me as a male, even though the new girl insisted on taking the other side.

"Which is?"

"A journey of self discovery," Rose answered.

"How perfectly cryptic," Alyssa said, as I was thinking the same thing.

"Now suck her dick, baby," Rose told me.

"Yeah, let's see how her self discovery is coming along," Alyssa said, still doggedly using feminine pronouns on me.

"Oh, she's already quite the cock sucker," Camry said, as I took charge of the big cock, wet with Camry's saliva.

That description didn't faze me, nor did Camry joining in with the feminine pronoun, since all I wanted at the moment was her... his... whomever's big cock in my mouth. It wasn't overly thick, but it was long... almost nine inches.

Instead of taking it in my mouth and sucking it, I revisited Sammy's earlier lesson and slid my tongue down one side of her shaft slowly like a sly snake, and then slithered it back up... lathering her cock with lust.

"Say now, that wasn't typical. Perhaps she is something," Alyssa said, as she looked down at me with dawning appreciation.

"She's a natural," Rose said, switching sides, but in a tone that could only be described as prideful. Whichever gender she considered me, I was her... whatever I was... which I found reassuring.

"And he hasn't been fucked yet?" Alyssa asked, also switching sides, which confused me.

"Only by my strap-on last night," Rose said, spilling not only to Alyssa, but also to my classmate Camry far more personal information than anyone should know. I felt my cheeks flush red as I took her cock in my mouth. Again like Sammy had taught me earlier this evening, I didn't take much of it in and flipped my tongue up and down, focusing on her cock head.

"Look, he's blushing," Camry said.

"I think she'll be blushing even harder when I'm nine inches deep in her pussy," Alyssa surmised. At which point I gave up trying to keep score. Probably Rose had it right in the first place... my gender was arbitrary, and was dependent upon whatever was going on at a given moment.

"I can't wait to see that," Camry said, as she grabbed the back of my head and shoved me forcefully forward, until I helplessly had nine inches of shemale cock in my mouth and Alyssa's balls resting against my chin.

"Shit, she can take it all," Alyssa said, sounding impressed, even as she kept referring to me with varying pronouns... as Camry held my head in place, requiring me to hold my breath.

"She's really coming along," Rose agreed, also using the feminine pronoun this time, as Camry let go of my head and I backed away, gasping for breath!.

"Now get sucking, slut," Camry ordered.

I obeyed, the usual excited versus humiliated battle going on inside my head and my body... even as my cock raged.

"She has a great mouth," Alyssa said, moaning ever so lightly.

"Yeah, she's a keeper," Rose agreed, and I thought it was so weird the varying ways she treated me... when we were alone it was sometimes romantic... just like we were a real couple... but not always... and at other times, like now, I was just a cheap slut for her... and for her privileged guests' entertainment... although all I'd taken to heart from her most recent four words was 'she's a keeper'. And if she truly felt that, then I was happy to live with all the rest, whatever it might turn out to be!

"Get her pussy ready, slut," Alyssa said to Camry, taking charge in a much more obviously dominant way than Rose ever did.

"Okay," Camry said, as she moved her hands to my hips and tugged, so I took the hint to shift from being on my knees, to on my hands and knees... while keeping the big cock in my mouth the entire time.

"Such a cock hungry slut," Alyssa mused humorously, as I was positioned like a sexual Barbie doll.

"And she still has a lot of training ahead of her," Rose added, as if trying to impress the pretty shemale.

"I can't wait to take her for a test drive once she's finished," Alyssa said, as I wondered while I sucked her cock and felt Camry's finger at my ass, what the other three people in the room understood 'once she's finished' to mean. Alyssa ordered

Camry, "Eat her pussy, you dumb slut."

"Sorry," Camry apologized, as submissive as a female as I was as a male.

I then felt her pull my ass cheeks apart and begin licking my ass, or rather my pussy, according to Alyssa. It felt surreal, but surprisingly good. Kinky, yet oddly intimate.

"Got any lube?" Alyssa asked.

"Yeah," Rose said, as I sucked cock and got my pussy licked... feeling even more feminine in this strange situation.

After another minute Alyssa pulled out of my mouth, and I watched as Rose coated her cock for my ass as she kissed the pretty blonde.

"All right, let's fuck this slut," Alyssa said, her voice feminine, but her tone masculine... she seemed to consider herself above Rose. So confident. So dominant. Or in other words, if there was a hierarchy between the four of us, I was definitely at the bottom, and Camry was obviously the next step up. Then it was unclear to me who was next. But if I had to guess, I'd have to choose Alyssa above my until now indomitable Rose. But it didn't seem like a major difference between them, since Alyssa appeared to be granting Rose at least a modicum of professional courtesy. Something Camry and I certainly weren't worthy to receive.

"Ready, honey?" Rose asked, looking down at me.

"I don't know," I replied honestly. Part of me was curious what a real cock would feel like inside me. Part of me was ready to take it in the ass, especially if Rose wanted it to happen. Yet this next step just added to what felt like the inexorable crumbling of my masculinity. Getting pegged last night was one thing; getting fucked by a real cock was quite another... although since Alyssa was a shemale, it wasn't really gay... or at least that's what I kept telling myself, as I felt Camry shift aside and Alyssa take her place behind me.

"Oh, you'll love it, honey," Rose reassured me, using the sweet term of endearment twice in a row just now... which made the upcoming sodomy feel more intimate.

"I've ended up loving everything else you've had me do," I said, as I felt Alyssa's cock poking at my ass.

"And you'll also love being fucked like a cheap cum slut," Alyssa said, as she pushed forward and filled my ass.

"Ooooooooh, God," I moaned... whimpered... actually, I can't describe exactly what manner of sound escaped my lips... as my ass was spread wide open.

"Oh yeah, this is a real cunt," Alyssa gloated as she began slowly to fill my ass... or rather my cunt... or... I wasn't sure what I was supposed to call it anymore.

Pain burned in my ass... which I assumed wouldn't ever happen to a pussy....

Yet as always, no matter how humiliating an act of submission I was subjected to... I could feel my cock throbbing.

"He's rock hard," Camry pointed out.

"Why isn't he caged yet?" Alyssa asked, as she was now resting against me, resting completely inside me.

"Like I said," Rose said. "She's still in training."

I didn't know what caged meant, but it didn't take a rocket scientist to figure out which part of me would be locked in some sort of cage.