Toby

I found my real self the start of this year.

A sissy gurl.

Okay so, going back I sucked at being a guy.

All through high school I never got laid.

Not even close.

I was a little short compared to the good looking guys at five six, I had unfortunately this whole soft chin thing and was never conventionally good looking.

Add that to me being poor.

Oh yeah poor was a definite thing too.

All my summer jobs just got stuff for school, clothes and a few things for like my hobbies and stuff but yeah I never had spare cash, never had a car, couldn't really be one of those guys.

I wasn't sporty, wasn't good looking, wasn't from the right family in town so all the cushy, good jobs went to the fuckers that didn't need the leg up. So they had the cash, the jobs, the cars, the girls.

So it was this kinda vicious cycle where my only way out was college.

I graduated and got s scholarship and fucked off.

And my first year at college was more of the same.

Second year I had zero fucks left and I went to a few parties and spent a good amount of cash on booze to bring to parties so even if I wasn't popular or attractive I was still sort of welcome.

And I mean I wasn't the only guy like me there.

So it all started after a party when me and some others were still drinking and cleaning up when we started talking about all of that.

The hot guys, the guys that got the girls, had the jobs, the cars, the cash.

We were mostly venting.

And then I met Jennifer.

And she point blank said. "You're a fucking beta Toby. why play by Alpha rules?"

"What?"

"You're a beta, you're not meant for this stuff as a fucking guy. Being male doesn't mean a guy, not these days."

"What? I'm not some tranny freak."

She looked at me. Truthfully she was cuter than she should be hanging out here with us. "You want to get laid Toby I'll do it. I'll suck your dick and let you fuck my sissy ass."

I looked her over and yeah she was cute, really fucking cute, flat as heck but...then it dawned on me...she was a guy.

"You're a dude."

She opened another can of beer and killed it pretty quickly. "No, I'm not a dude. I might have been born a guy but I'm so not a fucking dude or a guy."

We stared at each other.

She said again. "I'll suck your dick and you can fuck my ass too."

I was drunk, horny and I nodded. "Not here right?"

"Come on back to my place and I'll show you reality."

My brain fixated on her soft shiny lips and I nodded. Jennifer took my hand and we left getting a cab to her apartment.

Well we made out in the cab.

I hadn't ever really kissed a girl but we made out. And even with Jenn being a guy she smelled fucking great. Some kind of peach perfume and like baby powder and it felt right at the time.

And her feeling and fondling my dick was amazing.

Another person's hand on your junk is ten times better than your own.

Super fucking intoxicating really.

And when we got there and paid she took my inside and we kept kissing to her bedroom and true to her word she set me on her bed and knelt and sucked my cock.

My first load was an early mess.

"Doesn't count Toby but still fucking yummers."

Jenn undressed and she was sexy as fuck.

Clear skin, make-up, these tiny titties and this erotic little dick offset by these sexy expensive looking panties.

She looked so sexy and cool with herself too.

Getting blown for the first times was amazing, Jenn's mouth was amazing, the fact she was so into it was amazing. And then she got things from her purse while doing all of it and rubbered up her fingers and used some lube and sank those fingers into my ass.

I was too much in need of her mouth, too into it all and seeking my cum to happen when she sank two fingers into my asshole.

I cried out.

I was freaked out.

She was fingering my ass.

Then she found my spot, my prostate.

And the pleasure made me gasp as she found it.

She blew me and finger fucked me and rubbed me off.

I came so much harder than I ever had jerking off. And Jenn made all the right sexy sounds as she drank down my cum.

And it got better because she never stopped finger fucking me, never stopped rubbing me off.

I cried, literally cried with tears streaming down my face as her fingers made me feel things I fucking swore were impossible. I got hard again and came again and she loved that too.

And she still kept going until I came again but not like before.

My dick stopped working, my balls were emptied and Jenn rubbed me perfectly, incessantly until she made me have a sissygasm.

I had fallen back after the first onto the bed and was just utterly at her mercy when she finger banged me to my first then second sissygasm.

I was reeling when she was done.

Well done until she went and got a few more things.

Before I knew what was going on there was a lubed vibe in my ass and she fucked me with it but paid so much attention to running that vibe over and against my sissy spot.

"That's it Toby, that's it give in to it, let it be fucking glorious, you're made for this. I made you sissy cum twice now, that's fucking proof."

She angled it, moved it, rotated it in my ass around my spot.

Jenn made me cum again and again.

Then she switched to a strap on cock.

Seven inches and wide and thick as she fucked me into two more sissygasms before my cock had somehow recovered enough to spurt out another load.

Seven inches openinging my asshole, spreading me wide, fucking me until I screamed over and over.

"Ohhhh, ohhhh fuck! Fuck yes, fuck, fuck, fuck meeee!"

Jesus...I really figured out that I loved this.

I was so fucking full, my insides clenched around this thing inside of me.

And it fucking felt good.

I figured out that I fucking really liked getting assfucked.

That trying to be this failing straight guy was really useless bullshit.

I cried, I cried for that death of that idealistic bullshit in the face of getting off, in the face of cumming so very hard.

Jenn pushed my legs up over her shoulders and fucked me long and hard like nothing in my goddamned life.

I've never in my life thought about this thick hard dick sliding in and out of me. Never though or dreamed on me even having a sissy spot or a sissygasm, never thought that I'd want this so bad.

And the rest of it.

Touching, being touched, being with someone else, being wanted.

After Jenn held me as I sort of drunk bawled and moaned and sobbingly bitched how no one would like me or love me.

And drunk thanking her.

In the morning I woke up cumming as Jenn was sucking my dick and vibing me right into another massive cum storm complete with a sissygasm.

And then she fed me her little cock.

And I sucked it.

And I liked it.

After that we smoked a joint and got seriously cleaned up.

She made a call to some guy named Danny and said she need a hundred bucks in her debit account and she took us out for breakfast at the Smithson.

A swank hotel just a block away and they had like a hotel restaurant people could go to and they knew her. I had my first really fancy breakfast in my life.

We kissed, well she kissed my sorry ass and in public too and gave me her number and said. "Call me when you want my ass Toby."

Life changed after that.

Still couldn't get laid and even the real gay guys had this whole hunky or cute standard.

And jerking off furiously when I could wasn't doing it either.

I wanted to be fucked again.

Hell I dreamed of it and being a chick like Jenn even.

So I called Jenn.

She invited me over and after a few kisses she dropped to her knees and sucked my dick.

"Beta me Jenn, fuck me again...please."

"Really?"

I swallowed and nodded. "Please, god I can't get that night out of my head."

"You want to go full beta?"

I nodded. "Yes, please fuck yes."

Jenn took me to her bathroom and got me to strip then take a dump then she had an enema kit and flushed my out.

"Sissy pussies are clean, clean pussies are what guys want."

It was freaky as fuck and kinda disgusting but at the same time when I was done I wanted to be fucked more than ever.

Next was the shower and Nair and getting rid of all my body hair.

Then getting sweet lotion all over my body and deodorant to smell like a girl and then she had clippers and a razor and buzzed off all my hair and shaved me bald.

"It's for the wig, you'll grow your hair out Toby but until then you need a hot looking wig."

And she had one for me this tumbled sexy brunette wig she glued on.

Then she plucked my brows, shaved me super close with my face and did my make-up and we even did fake lashes and press on nails.

I looked nothing like the old me.

I looked sexy, hot, fuckable.

I got hard and she sucked my dick then lubed and fingered me until I came and until I had a sissygasm.

Then the doorbell rang.

And Jenn let in six guys, six of these frat guys I've seen around and they brought booze and she turned on some tunes and sat me on the couch freaked out and naked and before I knew it he had his hard dick in my face.

Dressed like this, and a hard cock in my face what was I supposed to do?

Of course I sucked it.

There's nothing like a good hard cock in your hands throbbing.

I was so fucking into it and liked it.

Of course I liked it that's what I was there for right?

I blew him and swallowed and two other guys as Jenn was too and then it happened.

Tyler, this good looking athletic handsome guy was behind me and sank my first hot hard live cock into my sissy ass.

I could not help by gurgle in joy of finally getting fucked around Peter's hard cock.

We fucked hard after that.

They fucked us hard after that.

Each one of them had a life shifting turn inside of me fucking my sissy ass until I came and came and came.

I lost track of how much cum they filled me with honestly and we got pretty drunk too.

Then the rest happened.

Jenn got us cleaned up, our make-up redone and she lent me some clothes and we took off with the guys.

We shared a cab van and we went out to the mall and we topped off out buzzes with going out to eat.

It was fucking awesome because we went for steaks at The Keg, they probably paid at least fifty bucks on my food alone and it was like no fucking big deal to them but I'd never been treated like this.

Jenn and I sucked all their cocks again in the restroom and then we went to the movies.

They were like gentlemen, the doors, talked nice to us, bought our tickets and snacks and even then still a little booze buzzed we had a great time seeing a movie that guys and I liked.

Then more dicksucking after the show and we went out for ice cream, then back to Jenn's place where we drank a little more and we all fucked again.

Slower this time, more relaxed with each other and still fucking awesome.

And that started me on this.

My life.

Our guys don't care about our dicks and honestly I don't either.

I mean we're sissies.

Which is actually fucking awesome.

All the mind blowing sexy I want, then there's clothes, dates, group dates and the longer it's going on the better.

I don't say no, don't want to.

I've been there, sometimes guys just want to have fun, get off have release without getting their ears talked off.

I don't bitch, I don't cajole or complain and any of that bullshit pussy girls do.

No periods, no drama...Jenn drilled that into me when I was first really getting into it.

No fucking drama.

And as a former guy I really get that.

Is it easy?

Yes, no...?

The dieting and working out is hard.

One, one meal a day everything else is an apple and water and a slimfast type shake for breakfast.

We spin class and we do hours on the stair climber for the best ass.

Hormones are freaky too but at the same time after a few months I've these budding sexy aching starter titties.

And they get in your head making you less a guy.

Still not a cunt.

Actually I'm better than that.

And the guys pay for everything.

My place, my own apartment if like crowd paid, clothes, utilities, even my health care. John one of my steady guys literally put me on his insurance.

Sure there's hate from some people. There's no shortage of bigots and hateful bitches too.

But I don't care i'm happy.

Hell even my grades went up as I switched classes.

I'm going to be a nurse.

I like taking care of my guys, I like taking care of people when they're not assholes.

And good money.

Even my folks are cool with this.

Dad freaked out and lost his shit for awhile. He's coming around as the guys have helped out getting me in better with him with cool guy stuff.

Seriously they got me good booze for him, models for his hobby, a box of cigars, I even saved up cash and got him a keg and a beer tap.

I'm ten times the better daughter than I ever was as a guy.

He's coming around.

And mom was freaked but she's cool with it as she and I get along better and I have a plan for my life.

I guess the point of this is.

Stop, stop being some failure as a guy.

Take the plunge, stop living by the stupid rules.

Be happy, suck cock, ride hard cock, be sexy, be awesome.

Try it, try it, be a sissy, be awesome.