Step Sister Corruption Part 151 – Day 77 Summer Loses her ‘A’ Virginity (fiction, M/F/F, d/s, teaching, step siblings, con, anal)

*Summer*

***GOD, JESUS, VIRGIN MARY, THE GHOST, HOLY SPIRIT, BUDDA, FLYING SPAGHETTI MONSTER, ZEUS, APOLLO, WHICHEVER OF YOU FUCKING DEITIES ARE LISTENING RIGHT NOW I SWEAR THAT I WILL BUILD A SHRINE IN YOUR FUCKING NAME RIGHT NOW IF YOU’RE ABLE TO KEEP GABE FROM TEARING MY ASSHOLE IN TWO!!!***

I was praying to every decent *deity* I could think of that would be able to save my ass right now.

And the motherfucker just started pushing his impressive member into me…..to be specific into **my** vir….well I guess my ass is no longer a virgin now is it?  Wait it’s still a virgin he hasn’t penetrated me yet. 

Unless you consider the plug as me losing my virginity then yes my asshole was no longer a virgin.

And then there was the dildo I was shoving up my ass before Gabe caught me.

Yeah I was no longer a virgin.

Jesus!!!!

Not even the dildo or plug hurt this bad.

Ok maybe the fat end of the plug did hurt a bit….ok it hurt a lot but Gabe’s fucking mushroom tip head pushing against my iris was a lot larger than that god damn plug.

I screamed, “I THOUGHT YOU WERE GOING TO BE FUCKING GENTLE YOU ASS!!!!”

I heard Kelly start laughing.

I looked at Kelly and snapped, “WHAT’S SO FUCKING FUNNY???”

Kel smiled at me, “He hasn’t even gotten the tip in yet.”

I need to bite on something…anything.

I clamped my mouth on the first thing I found….a pillow.

I felt tears running down my face so I clamped my teeth into the fluffy object and was suddenly reverting to my baser instincts as I was shaking my head like the object had *the* most delectable meats imaginable the only thing keeping me from the meats was the stupid cover.

I wouldn’t be surprised if someone compared me to a rabid dog at the moment with my mouth foaming from what was happening behind me.

I heard my tormenter….I mean lover….no he’s definitely **my** tormentor as he was pushing his member into me and him speaking softly, “Remember to relax or this is going to hurt.”

I let my mouth go and yelled, “FUCK YOU!!! YOU RELAX!!!”

I heard Gabe, “Summer….it’s me.  Just relax and calm down.  I promised I’d be gentle.”

I sighed….I did say he could take me…damn it.  And he did promise me that he would be gentle with me.

Sure as fuck doesn’t feel like he was being gentle at the moment.

I sighed and *tried* to relax but I don’t care who you are the first time I got my V card removed I fucking tensed as my hymen was broken.  And there was no damn hymen in my fucking ass, just my tight balloon nut.

I turned my head so I could look up in my position to look at Gabe, “Could you at least use more lube?”

Gabe smiled at me, “Babe if I use any more lube I’m afraid our own country might invade us for our oil.”

I looked at him dead pan.

Did this mother fucker fucking joke?

I looked at him serious and spoke very clearly as I enunciated every word, “I….SAID….USE….MORE….**LUBE**!!!”

Gabe shrugged and grabbed the bottle of lube that Morgan had retrieved for this particular activity to show me he had it. He turned the bottle upside down and squeezed as I felt a nice stream of cold ass fucking lube hit my asshole and traveled down to my pussy.

He looked at me with a smile, “Happy?”

I nodded.

He resumed and I felt his tip touch my asshole before I felt the pressure against my rear iris and I felt the familiar pain….only a magnitude larger.

He stopped and spoke, “Remember to relax.”

I felt the pressure.

He spoke, “Relax.”

Pressure….pain.

“Relax.”

Major pain as I felt the tip beginning to slip into my iris…the lube barely fucking helping.

“Relax.”

I felt my asshole stretch wider to what felt like a mile wide.

My body started glistening from sweat as pain washed through my body demanding I run away from the dick trying to penetrate the wrong fucking hole.

I prayed ‘*Please don’t let Gabe break my asshole!!*’

Unbearable pain now.

I felt my asshole beginning to tear.

I prayed harder as I chewed on my new toy…the pillow as it helped muffle my scream.

I swear I heard my body pop and felt my asshole begin to shut…just a little bit but the oak tree hiding behind the massive mile wide fucking tip kept my asshole from closing any more.

Gabe spoke calmly, “There you just took the tip. Good job babe.”

I knew tears were freely flowing down my face.

Only problem I didn’t know if it was from the pain or happiness that my asshole didn’t tear into two.

I felt Gabe put his hand on the swell of my back as he spoke the most stupidest question I have ever heard in my life, “You ready?”

Am I ready?

Are you fucking joking me?

I feel like I should get a big giant fluffy stuffed teddy from the top shelf for surviving the ring toss from the fair for having my rear ring stretched to the size of a fucking crater.

I felt my asshole moisten as I fucking freaked out, “What’s that?”

Kelly spoke softly, “It’s just more lube honey.”

Good I’m not bleeding.

Then I gasped as I felt the massive tip hiding just beyond my asshole start to travel deeper into my bowels causing my eyes to get the widest they have ever been.

The further the tip travelled into me I swear I could feel my asshole stretch as Gabe’s impressive girth that I so loved inside my pussy I now fucking dreaded as it stretched my asshole even wider and pain shot throughout my body.

I moaned, “Ffuucccckkkkkk!!!!” And more tears flowed down my face.

I felt my asshole slowly stretch wider as the massive fat fucking oak attached to Gabe slowly went deeper and deeper into my bowels shooting nothing but pain making my face stained by tears as I was ready to almost faint. The only thing keeping me from passing out was the continued pain and my bowels making me feel completely stuffed.

After what felt like an eternity of having my asshole stretched as Gabe’s impossibly wide ass girth that felt like I was millimeters away from my precious rear iris tearing and me getting a free hospital stay I finally FINALLY felt Gabe’s hips meet my ass cheeks.

*THANK YOU!!!!! THERE IS A GOD!!!!*

AND MY ASSHOLE IS ONE PIECE…..I think.

But now I feel stuffed to the brim, which is the weirdest feeling to have your anal cavity filled and it wasn’t shit but somebody’s dick.

My thought didn’t escape me but the pain was too overwhelming to appreciate the irony.

Gabe spoke, “Was I gentle enough babe?”

I looked at him and thought I’d be diplomatic, “Yes baby. Thank you.”

It sounded a lot better than chewing him out….or asking if my asshole has torn and bleeding.

He smiled and started pulling out as I felt great relief as I felt his impossibly long fucking cock slowly leave my bowels and my asshole slowly started to close as his girth slowly became smaller until I felt his mushroom tip knock on the back side of my balloon nut and had to refrain from grunting to *help* push the dick out effectively shitting out Gabe’s dick.

My relief was very brief as I grunted and gasped with a long curse resembling *fuck* but my gasp cut it short as my insides were re-invaded with Gabe’s length and my asshole stretched again as his girth stretched it back out.

I got to replay my previous emotions of pain and praying as it felt longer and wider the second time.

But once again my asshole never tore as Gabe’s hips pressed against my ass cheeks.

Then once again I felt tremendous relief as his cock left my insides only to re-enter my rear.

Each *stroke* I felt nothing but pain as there was no fucking *pleasure* in this damn act.

I was beginning to feel that this whole *let Gabe take my ass* was nothing but a huge fucking mistake.

How in the fuck do girls enjoy this?

Then somehow it happened….I started feeling pleasure.

I blinked once I felt that usual *feel good* start to build in my body…and build….and build.

I don’t know when it happened but somehow I was beginning to enjoy it as the pain slowly subsided and the same feel good in my pussy was starting to quiver telling me I would be approaching an orgasm.

Soon I was begging Gabe to go faster. Go harder. To pound my ass like a Congo drum.

Gabe answered my begs as he increased his tempo.

I was actually enjoying this.

Maybe having my ass fucked wasn’t so bad.

Each stroke was hitting something hiding in my ass that was making this pleasurable.

Soon I felt my first ass-gasm….and it was fucking ***STRONG***!!!

I screamed as my ass-gasm also fired off an orgasm in my pussy making the ***feel good*** slam throughout my body like I was ran over by an orgasm bus……a thousand meter long bus…….as tall as an oak tree.

My body locked up as the waves of euphoria slammed against my mind easily destroying my brain and was seeing stars.

Gabe didn’t stop fucking my ass making my orgasm last longer until it finally subsided and I officially collapsed into a heap as my brain’s synapses were completely misfiring from the strong orgasm that slammed against it.

I don’t know how long Gabe was destroying my ass but the pain and pleasure built up another orgasm and soon I felt another *strong* orgasm wash and radiate throughout my body again.

And again.

And again.

Then it happened, I don’t know how long Gabe had been destroying my ass and I sure as fuck lost count of my ass-gasms long ago as time seemed to be relative at the moment, but I felt for the first time *the* warmest fluid shoot into my anal cavity giving me *the* weirdest sensation I had ever felt in my *life*.

With Gabe’s orgasm over I felt his metal like rod begin to soften and my asshole’s strength begin to win as it tried to close around the flesh object as it left my anal cavity until the impossibly fat tip shook hands with the back side of my asshole and felt a lower level of pain as the tip softened enough until it finally left my asshole.

It was finally over and my collapse was finished as I sprawled onto the couch.

Happy the act was over and having cum in a place it shouldn’t be that just felt wrong and weird. But at the same time right as I had a new understanding for the act.

Maybe having anal wasn’t so bad after all. You know after the soul searing pain there was actual pleasure though I was so ready to run away before that even happened. So maybe just maybe having Gabe take my ass was worth it all as the act was pleasurable *nearly* as good as my pussy especially if the orgasms were this good if not better.

I panted in place and heard Gabe, “So How was it?”

I smiled and looked at him deciding to answer his stupid question with a question of my own, “Are you an anal man now?”

I got my answer in a smile as he kissed my forehead.

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