Hypnosissy 06: Educated to be Pegged

It was I who led us forward when I asked, "So was the message of all those videos that tonight I'm to let you fuck me?"

"Maybe," she smiled, all singsong.

"Ever since Sunday night, lots of guys have assumed I was a bottom," I said.

"Well, a real man is willing to take the feminine role as well as the masculine," she said.

"What does that mean?" I asked, drawn in by every word she said.

"Well, of course, sometimes you're the fucker... and I'm the fuckee," she said.

"Of course," I said, hoping that would be the case at some point tonight.

"But for a relationship to really work," she continued, "I believe the man must also be willing to serve as the fuckee."

"Oh," was all I could say.

"To feel like the woman," she said, before adding, "even to become the woman."

"Makes sense," I said, her logic indeed making complete sense to me.

"Are you ready to truly explore your feminine side?" she asked, a nylon foot stroking up and down my leg.

"Yes," I answered weakly.

"I'm about to take you to an entirely new place," she said, getting off the bed.

"A whole new world," I sang the catchy Aladdin song.

"Now wait here," she said, as she went into her walk-in closet. A room that I imagine most girls in a dorm don't have.

"Okay," I said, assuming she was putting on a strap-on.

I waited in the bed, my cock hard, waiting to be sodomized.

And of course I was right. She sauntered back out wearing just a smile, stockings and a strap-on.

I couldn't explain it, but as I gazed at her in all her beauty, and with her cock, I knew I was in love.

In love with her.

In love with what she'd made me into.

In love... as strange as it sounds... with the man I had become.

I said, "Nice cock."

"Ditto," she said, looking at my raging hard-on as she rejoined me on the bed.

"I can't believe we're about to do this," I said.

"Do what?" she asked coyly.

"Give you my anal cherry," I said, with no shame at all... only acceptance.

"God, you say the sexiest things," she smiled, her smile so sexy and charming.

"Please fuck my ass, Rose," I said, wanting to give myself to her in every possible way.

It wasn't until then I noticed she had a bottle of lube in her free hand. "Let's get your virgin asshole nice and ready. Get on all fours."

"You say the sexiest things," I playfully repeated her words as I obeyed her instructions.

"I've been looking forward to this all week," she said, as she poured lube between my ass cheeks.

It was surprisingly cold. It made my entire body shiver as I said, "Just the last few days for me."

"I imagine a couple weeks ago, this wasn't even on your sexual radar," she said, as her finger rubbed around my hole.

"Before you, none of this had ever crossed my mind," I said with a soft chuckle.

"And now?" she asked, as her finger prodded at my anal entrance.

"I...um...ooh..." I gasped as her finger slid completely inside me. "I think you've created a monster."

"You're my Frankenslut," she joked, as her finger wiggled around inside me.

If you've never had anything in your ass... there's no way to properly describe it.

Weird... yes.

A little uncomfortable... yes.

Surreal... yes.

Arousing... oddly, yes.

I imagine if you're a women you're used to the feeling of having something inside you... but for a man it was surreal.

I felt my feminine side taking over.

Just allowed myself to be penetrated.

To just let go.

"Pretty tight in there," she said, as her finger kept wiggling around inside me.

"I hope so," I said, not feeling much pleasure but also feeling only a slight discomfort.

"Don't worry," she said, as she began slowly moving her finger in and out. "Once you get used to it, you'll be screaming in pleasure."

"I'm not certain you understand how much I trust you," I said, "it sounds trite to say I trust you completely, but I can't think of any better way of putting it."

"I do know how much you do, because you've been proving it ever since the day we met, and tonight more than ever."

"By the way, I need a date on Wednesday for my mom's 50^th birthday dinner," she said, completely out of the blue.

"Are you asking me out?" I asked, finding this more surreal than the fact she was finger banging my ass. I mean everything else she expected of me had been telegraphed by the videos. Now as she prepared to sodomize me, she was talking about my meeting her mother and assumedly the rest of her family.

What did this mean?

Could she possibly become more than just my sexual mentor? Also my girlfriend?

The mixed signals I'd always gotten from her were very confusing... I imagine like I'd given to many girls in my past encounters.

I realized the obvious, as I felt her push a second finger inside me... creating a sudden burn... I was to be the girl not only during tonight's bed play, but also in this relationship.

"This may sting a bit," she said, as my ass was unnaturally widened.

"A bit?" I asked as I felt a surprisingly sharp pain.

"Okay, at first a lot," she admitted. "But don't you jocks say no pain, no gain?"

"I may have used that phrase a time or two," I said through gritted teeth as two fingers gaped my ass.

"Well, once the pain subsides, I'm going to give you pleasure like you've never felt," she promised.

"Okay," I said, as I just tried to relax.

"I promise," she purred, as she rubbed my back gently with her other hand.

"Okay," I repeated.

For the next few minutes I just closed my eyes and allowed her to gape me with two fingers.

She then asked, as the pain had largely dissipated, "Ready to get fucked, Brian?"

"Yes, fuck me, Rose," I answered, as her fingers left my ass and I suddenly felt empty.

I felt her hands on my hips and her cock poking at my open hole.

"Please, fuck me, Rose," I begged, wanting that cock inside me. Wanting to be fucked. Needing to be fucked.

"You're such a needy slut," she teased as I felt her penetrate me.

"Oh, yes," I moaned as her cock slowly filled me.

"You're my sexy slut," she added.

"Oh yes, I love being your slut," I moaned, knowing I'd do anything to be with her.

"I know, baby," she said, as she was suddenly leaning on me. The entire cock was inside.

Yes, there was a burn.

Subtle.

But I didn't care.

I wanted the pleasure she and a few men had promised.

I wanted to feel my prostate pleasured.

I wanted to feel what being fucked felt like. More than one guy recently had suggested I was a future bottom or a future two-hole fuck slut.

"So full," I moaned, wanting her to know I was feeling good.

"Comfortable?" she asked.

I laughed. "I don't think that's the right word, but I'm in awe that I have a cock in my ass."

"You like it?" she asked, as she slowly began fucking me.

"I do. It's unlike anything I've ever felt," I admitted, the pleasure totally different than fucking or sucking.

"You look so sexy with my dick inside you," she said as she slowly fucked me.

"I feel sexy being fucked by you," I moaned, the pleasure continuing to build... I suddenly realized that my cock, which had gone flaccid during the anal gaping, was hard again.

"I'm going to fuck you to heaven," she pledged, as she began going just a little bit faster.

"Oh yes, fuck me like a slut," I moaned, wanting to get fucked... and fucked hard. Just like sucking cock, if I was going to do it at all I was going all in... or in this case it was going all in me.

"You want to be my little fuck slut?" she purred, as she squeezed my hips.

"Yes, Rose," I moaned, the pleasure building... a pleasure that somehow touched my prostate and like Mr. Watson had said, flowed through my entire body. "I want to do everything with you."

"I want to do everything with you too," she said, which brought its own level of euphoria. The idea we could be ongoing partners in crime was amazing.

"Oh yes," I agreed, not wanting to talk anymore... I just wanted to get fucked.

"You're enjoying this now," she read my mind and moans.

"So much," I moaned, a sound coming out of me that was so feminine I didn't recognize it as my own.

"Now I'm going to take you to heaven," she said again, as she held my hips and slammed into me.

"Oh fuck!" I screeched. It was both a feminine and masculine sound that expressed both the pleasure and pain that coursed through me as she plowed deeper into me.

"Oh yes, baby," she purred as she started fucking me hard. "I'm going to fuck you like the little slut you are."

"Oh yes," I agreed, "fuck me... I'm your slut... so good... oh fuck!" Those few words took me almost a minute to utter as the pleasure consumed me and I panted like a bitch in heat.

And for a couple more minutes... I was fucked... hard.

It was indeed heaven.

Pleasure unlike anything I'd ever felt.

Being the fucker was one type of pleasure... being the fuckee was a completely different type of pleasure.

Both were good.

Both were great, even.

Yet this pleasure was somehow more body-consuming than when I was the one doing the fucking.

My balls boiled.

My cock ached.

I needed to come so badly!

When I was fucking a woman I knew when her orgasm was close... I knew when to really fuck her hard and not slow down at all.

At the moment... I was the woman... and my orgasm seemed imminent... yet I was powerless to do a damn thing about it.

"You need to come, baby?" she asked as if reading my mind.

"So badly," I whimpered.

"Good sluts can come just from getting ass fucked," she said.

"Really?" I asked, this seeming impossible.

"Oh yes, my little slut," she said still pounding me hard. "Don't you dare touch your cock, just revel in what you're feeling. You'll see, bimbo-girl."

"Yes, yes, call me names," I begged, knowing for some reason, perhaps the hypnosis videos, that being called names usually enhanced the pleasure.

"You're my cock sucking, ass taking sissy," she said.

"Oh yes," I moaned.

"My cum-craving slut."

"Oh fuck," I moaned, feeling like I was about to come at any moment... I could feel my cock pulsing without being touched.

"My pussy boi."

"Yes, yes," I said, as pleasure cocooned me.

"Come now, my bitch, my slut, my sissy, my cock sucker, my cunt muncher," she listed, each filthy term making my cock twitch and my body shake.

"Right NOW, you fucking whore," she demanded in a firm dominant tone that only enhanced the pleasure more, slamming me as hard as I imagine she possibly could.

I screamed as my cock spewed its load all over her sheets. "Fuck!"

"That's it, you dirty ass slut," she encouraged, as rope after rope spewed out of me and she continued fucking me.

"I love you so much!" I declared, as my entire body felt pleasure like I could never have imagined. It wasn't until a few seconds later, as she slowed down and I collapsed onto the bed and splashed down into my own cum, that I realized what I'd just declared.

She didn't respond in kind, or at all, which made me anxious about what I'd expressed in this moment of perfection... although I'd definitely told the truth... I loved her perfect body, her twisted mind and her ancient soul.

She pulled out a minute later, flipped me onto my back as if she were the man and I the girl and straddled my face. "Fucking you got me so wet and horny."

"Well, I am quite hungry from that hard fucking," I said, as I gazed up at her glistening wet pussy.

"Then eat away," she said, as she lowered her pussy right onto my face.

My body was still trembling with pleasure as I began licking my first pussy after a plethora of cock.

It was a different task.

A different technique.

A different taste.

And even with all the cock I'd sucked, all the cum I'd swallowed, there was still nothing that could match Rose's pussy.

Exotic.

Sweet.

Captivating.

I lapped as her scent engulfed me in my face's tight space.

She really must have been horny from fucking me, since in only a couple minutes she was grinding on my face and I was splattered with gushes of her cum.

I eagerly lapped up her cum... male cum... female cum... each had its own unique taste.

When she weakly got off me, she rolled into my arms and said, "That was amazing, babe."

"Agreed," I said, as we shifted from hard ass fucking and rough face grinding, to gentle cuddling.

"And," she began, as she placed her hand over my heart, "I think I may be falling in love with you, too."

My eyes went wide... my heart started beating twice as fast... those words were music to my ears!

Could I have it all?

Cock!

Pegging!

Perhaps a series of real cocks in my ass!

All that and love too?

As I pondered what appeared to be a heavenly future, she began snoring.

Obviously this was just the beginning.

THE END

The series could easily end here, as it's a natural place to end.

Or Brian's story could continue with:

HypnoSissy7: Faggot for BBC

A BBC two-hole gangbang and a bukkake.

HypnoSissy8: Feminized Cock Sucker

Rose begins to feminize her cock sucker.

HypnoSissy9: Fucking xxx(not sure who?)

Brian's task is to crossdress and seduce xxx?

Other Ideas? Send away.