NOTE: Life gets in the way sometimes, but here is the next chapter. This one is almost 11,000 words. Strap in and thank you all for reading!
*****
My best friend Jonathan had just caught me slamming myself full with a monster dildo. I had just had one of the most intense orgasms of my life. I was still panting from my brutal self-inflicted ass-fucking. And, butt naked on the bathroom floor, I was helpless.
"Go fuck yourself! Get out!" was all I could manage to blurt.
"From all the noise you were making in here, I thought you needed help. You nearly pulled the door off its hinges. Looks like you have yourself all taken care of," Jonathan winked.
"Close the door!" I said. I clambered toward Jonathan on wobbly legs. I pushed him out and shut myself in the bathroom. I could see myself in the mirror and knew I looked like the absolute biggest ass slut. My own cum was dripping down my body and my hips were cocked at an angle that said, "fuck me hard!"
One side of me was mortified. The other was excited and encouraged. I traced my fingers along my bare skin and shivered, arching my back.
I was snapped back to reality by Jonathan on the other side of the door who said, "you better get your ASS in the shower before the rest of the house gets back!"
Shocked into action, I jumped into the shower and rushed through my shower. I washed away any evidence. I even quickly plunged two fingers into my pliable asshole (causing a shameful moan, and a wealth of goosebumps).
Leaping out of the shower, I furiously dried off. Then, I snatched the dildo off the floor and cleaned up the pool of my cum with my towel. Lastly, I quickly washed the dildo in the sink, whipped my dirty towel over my shoulder, and dashed for the door.
I tiptoed my way to my room, nervous that people were home. I took a deep relieved breath when I reached my door unscathed. That wasn't going to last.
I opened the door. FLASH. I was blinded. Jonathan was standing in my room with his Polaroid camera he would use at house parties from time to time. BZZZ. The photo was ejected. Jonathan held it up.
As it developed, I could see my shocked face, the cum soaked towel, the gigantic dildo in one of my hands, and my cock (clearly semi-erect).
I glanced down to see that my cock was indeed swelling.
"What the fuck, dude?" I said, lurching forward.
Jonathan pulled the Polaroid out of reach and ran for the door. I tried to catch him but was out of luck. He whipped around and teased me.
"Relax, no one is home yet. And, THIS is just a little insurance. I couldn't resist," he said waving the photo.
Furious, I made the move for the door. Suddenly, we could hear the sound of a key being inserted into the front doorknob. Jonathan backed into the entryway as I swiped at him. The front door opened and I hurried back to safety. I slammed my bedroom door and locked it.
"Hey, Jon, you're back early. What was that about?" said one of my housemates (who I'll call Kris) on the other side of the door. Kris clearly heard me slam it in a tizzy. Ugh.
"Oh, just Damien. He's a little BUTTHURT that Summer broke up with him. But, I think he's found something to fill the void," Jonathan loudly spouted.
His wordplay was not lost on me. Dick.
I fumed. I had been caught. Exposed! And, Jonathan had evidence! I was doomed. I hung up my towel, stashed the dildo, and dove under the covers hoping to disappear.
—
For the next week, I avoided Jonathan like the plague. No lunches. No regular workouts. No texts. No hangouts. No parties. No nothing.
Of course, it was tough as we lived in the same house. But, when I would see him, I would make a break for the solitude of my room. I hoped this would do the trick for the rest of the semester.
Unfortunately, as we had just returned from Spring Break, a couple of months of the school year remained. My tactic of avoidance was bound to fail. Plus, I wasn't exactly avoiding 'high-risk behaviors.'
Just two weeks after being caught, I was back at it. I was desperately horny, naked, stroking my cock in my bed under the sheets, and prodding the big fat dildo against my lubed up asshole. My chest was heaving.
It was so hot.
In my head was the memory of being caught red-handed (or with a huge mock-cock balls deep in my ass). It was mortifying. And yet, it drove me wild how dirty I felt. The taboo of it all made my cock rock hard. I knew I had cum harder than ever slamming my fuckhole full with a big rubber dick.
Such a slut.
So, again, there I was two weeks after 'The Incident.' I was in my room, teasing myself mercilessly. I knew what I had to do. I was desperate for a mind shattering orgasm. I needed to press every last inch of that toy back into my ass and surrender to its pleasure.
I started slowly.
I pressed just the head of the dildo into my asshole. I paused. I tugged it back out. Then, back in as I stroked myself gently. I could feel every bit of my energy being channeled to the depths of my ass. A fire was starting to spread deep inside of me.
Methodically, I pumped just the tip of the monster toy past my opening. Again and again it stretched me until any discomfort passed. The discomfort was replaced with a feeling of increasing pleasure that would crash in waves the deeper the toy plumbed my depths. I whimpered as I personally ingrained in myself a sensation without which I would no longer be able to function.
I worked the toy deeper and deeper, continually applying more lube. When I finally couldn't wait any longer for the full length, I hovered my ass over it. I was ready to plunge it deep in a slow and focused manner. Then, I heard two knocks.
Without so much as a pause, Jonathan BARGED through the door.
I had forgotten to turn the lock! I had no time to prepare. It scared me half to death. I dropped myself to the mattress.
The dildo broke my fall.
Every last realistic bit of that 9-inch long 3-inch wide monster was drilled into me. It stretched me wide open. I almost passed out.
I wasn't as ready as I thought.
Jonathan stumbled over and crashed down on the mattress. He was drunk. I struggled to contain my emotions, but generally kept it together.
"Sorry about walking in on you in the bathroom. I feel like such a dick," Jonathan said, genuinely guilty.
"Don't worry about it," I said considerably strained.
"I mean it, man. It was uncalled for. I even deleted that picture I took," he said with wobbly intonation.
The pressure was building. The toy had definitely hit a number of buttons inside of me. I was barely able to suppress the moans begging to get out. What I definitely couldn't suppress was a slow rhythmic rolling of my hips that started to propagate.
"Ohhh...thank you...uf...I really appreciate that. Would you please go to bed? I'm trying to...mmf...sleep," I barely managed to utter.
"Can I make it up to you? I'll buy you beer...or or or lube...or something?" Jonathan stammered.
"Nnng. You sound ridiculous. Ah. Get out please!" I said in desperation.
"Where is it?" he asked, getting to his feet.
I didn't understand.
He staggered to and fro until his eyes settled on the gift box on its shelf. He snatched at it, knocking it to the floor. The lid popped off and the contents spilled out. Of course, the massive toy was conspicuously missing.
He looked to me confused. Still lightly gyrating my hips, I was lost in euphoria. I am sure he could see my face turn 12 shades of crimson. I was never a good Poker player.
"Oh, I see. Is someone having a little me-time?" he sassily asked.
"NoOoOooo," I replied. I couldn't stop bucking my hips. Seriously, who was I kidding?
Jonathan approached the bed. I grabbed the base of the dildo still pressed into me and scooted myself up on the bed nervously. This only served to jam the toy into me once I came to rest.
"Oh God!" I let slip from my mouth.
"Yeah? You love that don't you?" Jonathan asked hypothetically.
With earnest, I bit my lip. I tried to force myself to shake my head emphatically "NO." But, all I could force was the huge toy deeper inside of me. I blushed so hard, my cheeks felt like they were burning.
I nodded and whimpered helplessly confirming my love for the stretching and filling of my asshole (as if it wasn't obvious).
Jonathan crept closer to the bed. He curled his fingers around the edge of the covers. Reflexively, I scooted further back, sitting upright for 'protection.' (Un)fortunately, this caused the entire length of the dildo to be buried up inside of me.
"Oooh, fuck ME," I gutturally moaned. I shifted back and forth. I was lost to the feeling.
In one swift pull, Jonathan yanked the comforter and top sheet off of me exposing my shame.
"It seems like you already have that taken care of..." he cheekily observed.
"Dick!" I slurred sloppily.
There I sat against the wall, a huge dildo penetrating me through and through. I was obviously completely naked with one of my hands wrapped around my pulsating hard cock. I was even still lightly stroking myself.
I snapped out of my spell.
I pulled my hand away from my cock and swiped for Jonathan. As my body chased the movement, I reached behind me and pressed the dildo into me to keep it in place.
I fell flat.
Laying there with the dildo held into me, my legs spread to either side, and my hard cock pressed under me against the mattress was surprisingly hot. Especially because Jonathan brought himself closer. He put his crotch in my face. Clearly, he was on a whole new level of drunk judging by the boldness he was exhibiting.
"You like that?" he asked. I have to admit, the outline in his pants was impressive. He pressed 'something' surprisingly hard and large against my face.
"Uh huh," I said writhing my face on his bulge, unable to control myself.
Jonathan grabbed onto my hand holding the dildo in place and pulled. The toy was withdrawn from it's resting place until just the tip was inside of my ass. He drunkenly asked, "No, I mean, do you like this?"
His brazen act kicked my heart rate into high gear. I was panting. I grunted, "Yes."
Then, he slammed the dildo back into my asshole.
I screamed into the mattress. My cock swelled and exploded cum against the bedding and my stomach. My legs twitched, and I convulsed moaning "YES, yes! Oh fuck yes!"
