Hypnosissy 09

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Brian begins his feminization journey.
12.2k words
4.75
75.9k
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Part 9 of the 11 part series

Updated 06/07/2023
Created 04/07/2016
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HypnoSissy Ch. 09

Summary: Brian begins his feminization journey.

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 ninth story will make more sense if you first read the first eight. 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, and 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 he gets 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 one, and getting blown himself.

HypnoSissy 8: Hot Shemale

Brian loses his actual anal virginity (meaning with an actual cock in his butt this time instead of just a strap-on) in a wild foursome with Rose, Camry and a sexy shemale.

And now... the next chapter of Brian's continued wild sexual awakening....

HypnoSissy 9: Hurtling Deeper into Submission

I slipped out of bed desperately needing to pee, and only then recalled I was wearing a cage around my dick. I sighed as I hurried to the washroom. I wasn't sure I could do my business standing up, so I sat down on the toilet seat like a girl... yes, like a girl... which was becoming pretty standard in my life in a number of situations.

I peed, which was awkward, especially because my post-pee shake was more difficult. I grabbed some toilet paper to wipe off the cage before walking back to the living room to find my underwear, which I couldn't find anywhere. I did spy a pair of pink panties beneath an easy chair, although I didn't know whose they were. I found walking around naked with the cage swinging freely a little awkward, since it kept tugging my dick down. I assumed underwear would make it sit still and solve my pendulum issue.

After looking around for a couple of minutes, even going into Rose's room and looking there too, even though I knew I'd been naked when I went there after my sodomy last night, I returned to the living room, really needing to deal with the pendulum issue, which was making the cage even more uncomfortable than just wearing it in the first place.

Alas, when I picked up the pink panties, just like any guy, I brought them immediately to my nose. Oddly, there was no scent at all. I shrugged and decided to see if they'd somehow fit me... as... you know the saying... desperate times called for desperate measures. I pulled the pink panties up my legs and over my caged bulge. They were extremely tight, but with a little wiggling around, which I assume looked ridiculous, my pendulum issue was solved.

What surprised me as I stood there in feminine underwear for the first time was how soft they were... so much softer and silkier than the underwear I normally wore. Fascinating!

So when Rose walked in, she found me stroking my hand over my own ass in those sensuous-feeling panties. "Well, don't you look cute!"

"Oh... um... I..." I babbled, embarrassed to get caught like this. "I couldn't find my underwear, and the cage was getting uncomfortable without any, because of... you know... pendulums."

"If that's your incomprehensible story, I guess you'd better stick to it," she giggled. "But no worries, I think you look adorable in those panties," she said, walking over to me.

"You do?" I asked, as she reached me, kissed me and brought her hands to my panty-clad ass.

"Sexy," she whispered, kissing my neck.

My cock began to grow.

"Hot," she continued.

My cock was restricted by the damn cage, so like it or not: no more growing.

"I think I want you wearing panties from now on," she adjudicated.

"Y-y-you do?" I stammered.

"You do seem to like them," she said.

"They are a lot softer than my usual underwear," I admitted.

"Yeah, the underwear industry has put a lot more effort into ladies' panties than they have into male boxers and briefs," she said, turning me on so much with her touch, her warm breath, and her sultry voice.

"That I can believe," I agreed.

"So why don't we go panty shopping today?"

"For me?" I asked, even though it was obvious.

"Well, I could use a couple new pair too," she shrugged. "But yes, mostly for you."

"I don't know," I said, this seeming like one more step towards gay.

"Are you second guessing me?" she asked, not in the frightening tone she'd addressed Alyssa with last night, but with hint of surprise.

"No," I said. "It would just be crazy difficult to conceal panties when I changed for the gym at school."

"Good point," she nodded. "So you'll only wear them on weekends, whenever you're with me, and after school," she decided.

"Do you think I really need to wear panties?" I asked, even though I liked the feel of the ones I was wearing, and loved that she thought I looked sexy in them... it just seemed too sissy-like.

"I do," she nodded. "Consider it another step in exploring your feminine side. Plus, they're a natural next step to your synchronizing with the videos you'll be watching next."

"They will?" I asked.

"Yes," she nodded. "How many have you watched so far?"

"Just the first one on my new USB," I said.

"Got it. So the next few will explore your feminine side in much more vivid detail than before," she said. "So your already wearing panties will put you a bit ahead of the game."

"Great," I laughed awkwardly, not sure what I thought of this... but knowing I'd do anything to make this amazing, complex enigma of a woman happy.

"Why don't we go out for breakfast?" she asked.

"Sure," I agreed, thrilled to be doing something normal with her.

So we showered together; I washed her, she washed me... but only in a playful way.

It took a bit of getting used to, but I became somewhat accustomed to walking around with a cage surrounding my cock... it was weird... but doable.

We went for breakfast omelets, where we chatted about the things normal people do. Travel: she was hoping to go to Italy this summer, which I'd visited twice, as my family was from there; school: she talked about her university classes, I talked about the scholarships I'd been offered for next year... since nobody ever talked about high school. We talked about best concerts we'd attended... hers was when The Rolling Stones had visited a nearby city as part of their Zip Code Tour in 2015, which I thought was way cool... I'd been to that concert too... although I had to say my favourite was Toby Keith, for which she teased me relentlessly (what can I say... I like both rock and country).

It was like we were a normal couple doing normal things.

At the strip mall, which had an adult shop, we first stopped at a vintage clothing store where Rose tried on a few dresses and I gave her my opinions, and we stopped at a vinyl second hand shop, where she picked up a Blood, Sweat and Tears album in mint condition.

It wasn't until we entered the adult shop when the façade of a normal relationship came to an end. Rose, still holding my hand, led me past the wild array of sex toys and directly to the lingerie area. She'd obviously been here before.

She went to a bin of panties in every imaginable colour, and then looked at me. "Are the panties you're wearing tight?"

"A little," I answered, just as a chubby woman in her forties arrived.

"Do you need any help?" she asked, and I wondered if she'd heard Rose's question.

Not that it mattered, since, "Yes please," Rose nodded. "What size panties should my boyfriend wear?"

My already red cheeks burned even brighter.

The woman looked at me, not at all fazed by the question, nor did she seem to be judging me. After a minute, she said, "Definitely a large. Unless you want anything in a European style; those would be an extra-large, since they fit small."

"Will the sizing change if he's wearing a cage?" Rose asked, giving this stranger way too much information about me, and yet speaking as casually as could be.

"Hmmmmmmmm, it depends," the woman pondered. "What size is his phallus?"

"Seven inches," Rose said.

"Then I'd go with extra-large for any style."

"Great," Rose said, and she pilfered through the panty collection and pulled out a few pair.

"With his complexion, red will look very sexy," the saleswoman suggested, pulling out a ruby red pair.

"Good point," Rose said, holding up a light blue pair. "How about these?" she asked me.

"I don't know," I replied, horribly embarrassed.

"Those ones are a sexy colour," the woman said.

"I think so too," Rose agreed.

"If you'd like any more assistance, please let me know," the woman smiled warmly.

"Thanks," Rose said, as she continued browsing through the plethora of panties.

"Silk or lace?" Rose asked me, holding up one of each.

"I have no idea," I said, hinting at how embarrassing this was.

"Then we'll get both," she shrugged, either oblivious to my discomfort or not caring.

"Okay," I said, not daring to confront her about my discomfort.

After a couple of minutes she seemed satisfied and said, "I think we have enough variety."

"Okay," I repeated, happy if we were getting out of here.

We went to the front, she paid for my panties, which made this excursion even more awkward, even though I was thankful I wasn't buying them.

Once outside, she said, "So we're going back to Plan A. I expect you to wear panties every day at all times, even while you're playing football."

"I guess," I said.

"You don't like the idea?"

"It just makes me seem even more feminine," I said.

"I want a man who can be a man when I need him to be a man, and a feminine slut when I want her to be one," she said. "Can you do that for me?"

"Yes," I answered, again willing to do anything for her, "but what about at school?"

"You can change in a bathroom," she shrugged. "your cage stays on at all times, even when you're showering, so you'll need to figure that out."

"Oh, I hadn't even thought of that," I said.

"So, panties only from now on," she said. "understood?"

"Yes," I said sheepishly.

"Have I steered you wrong yet?" she asked.

"No, but the risk of getting caught keeps increasing," I said.

"Which turns you on, doesn't it?" she said, as she lovingly took my hand and led me to the car.

"Oddly, yes," I admitted.

We reached the car and she said, "Look, I like you, I really do. I think you're special. But I need to know you're completely comfortable with who you are."

"I was before I met you," I pointed out.

"That was a façade," she said. "I guess I mean I want you completely comfortable with who you're becoming. Or if you aren't 100%, you're at least doing your best to get there."

"But I don't even know what I'm becoming," I said.

"Yes, you do," she smiled, leaning in and kissing me. "Or at least you do deep inside. You just may not have accepted it yet, and the videos can help you with that."

She then walked around to the driver's side and got in. She drove me home, and to my surprise asked, "May I meet your parents?"

"You want to meet my parents?" I asked, this overture somehow surprising me.

"Sure," she said. "You're meeting mine on Wednesday, and I am your girlfriend, am I not?"

"Yes, yes you are, and I'm thrilled about it," I agreed, loving to hear her admit it.

"Great, then kindly escort me in and introduce me as such," she said, as she got out of the car.

"Okay," I said.

I won't bore you with the details except to say I was thrilled to introduce her as my girlfriend, and my parents loved her... she stayed for supper... and she behaved herself as my perfectly sweet girlfriend.

Once she was gone, and we'd finished the chat with my parents about how great she was, I was in my bedroom, wearing just my panties (and cage), and pressing Play on Video S2.

The video began by introducing a term I hadn't seen used before... and even now it wasn't specifically mentioned... at least not for a while... but it was strongly implied over and over. The term was 'sissy'.

A word I immediately disliked as much as faggot.

It was demeaning.

It was judgemental.

It put the viewer (me) in her place.

As a girl in sexy lingerie slowly got fucked, a sultry voice said: "I know what you want to be."

A Chinese girl spit-roasted by black men: "I know the position you want to be in."

A MILF receiving a massive load all over her face: "I know what you crave."

A shemale blonde riding a cock... her own hard cock bouncing all over the place: "I know who you really are."

A black nurse on her knees sucking a huge white cock: "I know where you want to be."

A pretty girl with a load all over her face walking proudly down a busy street: "I know who you really are."

A hot shemale stroking her dick while fucking her ass with a huge dildo: "I know what gets you off."

A drop-dead gorgeous redhead in a short dress posing sexily: "I know who you want to be."

A close up of a big cock shooting a load: "I know what you want."

A close up of a pretty girl being coated with cum from at least a dozen cocks: "I know what you need."

My cock was desperately trying to break free from its steel cage, but to no avail, as the hot images had me crazy horny, but it was only flesh and blood instead of birthed in a foundry.

A pretty girl put on a pair of pantyhose: "I know you want to."

Another girl slid into a sundress: "I know you want to."

A blonde applied her lipstick: "I know you want to."

I was captivated by the woman's voice, and it drew me in... mesmerized by her words and these images of beautiful women doing sexy things.

A girl already coated in cum stroked two cocks while sucking on a third: "I'm going to teach you how..."

A girl in a cheerleader outfit was triple teamed: "How to be her. "

A shemale was on a bed lying on her back propped up slightly by a pillow, sucking one dick while being fucked by another one: "How to be her."

A black shemale at a glory hole bouncing her 'pussy' back onto an unseen cock... as she stroked hers: "How to be her."

A woman in a wedding dress, on her knees, sucking a priest in church with her hands pressed together as if in prayer: "How to be her."

Then a dozen extremely brief scenes... all of them shemales performing sexual acts... as the voice said each time: "And her."

A man in a suit methodically undressed and redressed into a woman in a dress, and then applied feminine makeup: "I'll help you shift from masculine to feminine."

A girl blowing a kiss: "Because you are feminine."

A girl wiggling her ass: "Because you want to be a woman."

A girl cupping her huge tits: "Because you were born into the wrong body."

A shemale being really railed with her cock and tits bouncing around: "Because you're a sissy."

Again a dozen quick scenes popped on and off of the screen... of shemales getting fucked, taking facials and sucking dick while a phrase repeated itself: "You're a sissy."

And although I hated the term itself, the way she was saying it, the way she was accusing me of being one, and the way she seemed to be seeing right through me... had me completely drawn in.

A woman in her sixties was devouring a massive black cock as the voiceover began a new train of thought: "Regardless of your age... because sissies can be any age at all."

A large woman was getting triple-teamed: "Regardless of your weight... only your mouth and your ass are important."

A Latina with a huge Beyoncé ass was ass fucked: "Regardless of your ethnicity or nationality... sissy cock sucking cum buckets inhabit every city and every country in the world."

A Muslim in a hijab was getting her face coated with six loads from six cocks: "Regardless of your religion... religion not being an effective barrier to a sissy accepting who she is. God, YHWH, Elohim or whomever you pray to did in fact create you, and created all sissies."

A chubby white woman was being spit-roasted by two fat black men as her husband watched and stroked his cock: "A sissy is a sissy regardless of her marital status... although most sissies are married... and most sissies hide behind the rings on their fingers."

A priest with a cross in his hand gets ass fucked by a shemale parishioner: "Regardless of your career... the more power you wield in your profession... the more likely you are to be a secret sissy... to crave cock in your mouth and in your pussy."