A Bisexual Mans Story Pt 01

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A Bisexual Man's Story (Part One)

Author's Note:

This tale is semi-autobiographical. Sincere thanks to my Literotica muse, sneaky_lola3, for setting a great example of joy in writing for your own pleasure, and then putting it out there for others to get off on.

Everyone in this story is over 18 years of age.

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Sexual fluidity is an approach to life that I have grown comfortable with.

In fact, I lost my virginity years ago to a guy named Brian, who was a close friend from my neighborhood. (The story is published here on Literotica in a three part series entitled "A Summer Affair".)

This new story takes place during my undergraduate years at University. I was only twenty years old and living with a petite brunette (nineteen years of age and also enrolled at University) who had the most beautiful tits and luscious pussy. Man, I was IN LOVE with Kelly, my sweetie-pie, and she was my Wild Party Girl.

Kelly could make you lose your damn mind having sex with her. She reveled in being an uninhibited little vixen in bed. The girl LOVED to FUCK and she demanded to be fucked hard every single day!

We had moved into a small, cozy house near the University, where I came home from campus each day horny as hell from being around all the young coeds. Sometimes I needed to beat off if Kelly wasn't home yet and shoot a massive load of hot sticky sperm all over myself. But I'd still be plenty ready to fuck her brains out that evening. My balls were so full of cum at that young age that I would need to clear the pipes at least a couple of times each day.

This was also around the time that I started to experiment on my own with prostate play by shoving things up my ass while masturbating. Geezus, those were some heady private sessions pleasuring myself anally. I was definitely a "closeted" bisexual in those days.

I loved fucking my girl, Kelly, but I craved anal penetration and was too shy to ask her to play with my bottom.

My favorite things at home to fuck my ass with while masturbating were bananas and cucumbers. What can I say? I'm a "back to nature" kind of guy....

I loved getting down on all fours in the kitchen with some hot porn. The curve of a thick banana would hit my prostate just right and send me hurtling towards a howling, hands-free orgasm pretty quickly, with my cum jetting out so forcefully that it splattered noisily on the tiled floor. The squelching sound of the banana reaming my rectum was so fucking erotic. It was such a turn-on to look down my torso and see my dick jerking up and down of its own accord between my thighs. Occasionally, I'd rub a little spit on the head of my dick just to tease myself, but mostly I'd cum just from pounding my hole. You see, I was clearly becoming addicted to the manly pleasure of p-spot stimulation.

Secretly, I longed for the excitement of a guy cumming in my mouth so I could swallow his potent seed. So it was a treat to eat my own cum as I lay completely spent after ass fucking myself.

A long, thick cucumber was my preferred improvised tool for anal masturbation. I loved to edge for at least an hour, if not more, before releasing a white hot load of slippery spunk. Lying on my back with my knees drawn up and pillows under my head, I would place a couple of old beach towels underneath me to cover our bed. I would then position myself so that I could watch my ass, cock and balls reflected in a full length, free-standing mirror at the foot of our bed.

God, how I loved to watch Kelly ride my stiff cock in that big mirror when we had sex together. Her cunt would get so fucking creamy and drip all over my balls, literally painting them white with her cum. And, oh my, her pussy juice was as sweet as honey nectar.

OK, returning to my self-fucking episode.... late one afternoon when I was home alone and horny as fuck, I laid down on our big bed and took my time slathering a nasty fuckboy concoction of Crisco & butter all over my penis, balls and asshole. I loved the way the depraved mixture made my dick glisten. Spying myself in the mirror, I languidly stroked my dick and squeezed my balls. My hand slowly drifted downward past my raging hard-on to slip a finger lovingly into my bunghole.

Burying my index finger up my ass all the way to the second knuckle, I gasped huskily as I tickled my prostate gland. Wiggling my finger in and around helped to stretch open my slutty orifice. It had been far too long since I indulged in my passion for bottoming, I thought to myself.

Straining and throbbing, my cock was already anticipating the intense release that would be its delicious reward. Pushing both my index and middle fingers together into my hole was now done at a slower, more seductive pace. As I penetrated further up my rectum, the pressure on my love gland pushed out clear beads of precum, which oozed deliciously from my dickhole.

I had to be careful not to cum too soon since the "main event" was coming up with greasy Mr. Cucumber! Vigorously fingering myself, lewd squelching noises emanated from my distended rosebud. Beads of sweat started to form on my brow. Oh my!!... suddenly it was quite warm in our bedroom and the musky smell of sex with myself was getting me high!

It was now time to thrust my fingers in as deeply up my ass as I could to ready myself for a good assfucking. The sight of my cock jumping and throbbing of its own accord was beautifully erotic. Panting hard to catch my breath, I paused to regroup before going forward with the butt-pounding that I so longed for.

Savoring my debauchery in the mirror, I reached for Mr. Cucumber with a sly smile. The phallus was already greased up with Crisco, so I took a moment to shove a quarter stick of butter up my naughty chute where it would melt deliciously, leaving my bottom all squishy and slick.

"Fuck me, that feels good!", I cried while dragging the thick cucumber over the shaft of my rock hard cock.

"Yes, that's it!" I spat while sadistically clutching my balls.

Thawck! Thwack!... the thick vegetable smacked against my ballsack, eliciting feverish sensations of pain and pleasure.

Wap! Wap! Wap!.. the sordid phallus slapped mercilessly against the head of my dick, causing it to turn an angry shade of purple! Holding my breath against the strain of not wanting to cum yet, I stared lustily at my obscene acts in the mirror.

"Remember, Kelly is due home in about an hour and you'll need time to clean up, you nasty slut!" I admonished myself.

Now, the slimy cuke slapped hard against my asshole, making my asslips quiver lasciviously. Flogging my anus made me groan with wanton desire. The rude fapping noises heightened my arousal.... making my bottom crave more nasty abuse. Closing my eyes, I breathed deeply.

"Is this what you want you nasty slut?"....my hand brought the thick cucumber shaft down even more forcefully against my palpitating boy-hole. My pouting asslips fluttered indecently, seeming to kiss the crude instrument of pleasure.

"Oh god, ohhhhh yessss, DO IT, motherfucker!" I grimaced.

Fap! Fap! Fap!.... the blows from Mr. Cuke rained down mercilessly on my pouty anus. Then.... Wap! The huge cucumber slapped viciously against my ballsack. Dropping the nasty vegetable, I grabbed my balls and twisted them harshly while spanking my straining boner back and forth with my other hand.

"You nasty slutboy! You fucking sluthole! I'll give you what you want!" I cried with tears forming in my eyes at the magnificent pain mixed with agonizing pleasure.

My orgasm was approaching too fast now and I needed to slow things down again. I ceased spanking my genitals and then bit my forearm painfully almost drawing blood. Closing my eyes, I bit my arm again more viciously to distract me from cumming too soon... then I began a brief interlude of self-soothing.

This had become one of those truly extraordinary masturbation sessions that I lusted after. It was the type of guilty pleasure that I was too embarrassed to ask Kelly, my girlfriend, for. I loved fucking her in a manly way, pounding her pussy into submission and making her groan in ecstasy while calling her my sweet dirty slut. But Kelly didn't know about my bisexual past and my anal fixation. I had fingered her tight bunghole many times while we fucked each other, however that was the extent of our assplay together.

Breathing slowly, I watched myself in the mirror as I lovingly greased up my nipples...rolling my taut buds between my fingertips and pinching & pulling on them seductively. Pulling hard on my sensitive nipples sent throbs of pleasure straight to my throbbing, abused balls. Reaching for one of the clothespins on the bed beside me, I knew what was coming. I'd only tried clamping and stretching my nipples once before and had almost shot my load just from that exquisitely painful stimulation.

Sighing anxiously, I clamped first one nipple.... Ouch!... and then the other.... Owwwww!! Then, looking through my legs in the mirror at my molested sluthole, I softly whispered, "You'll get yours in a minute, honey."

What a sight I was with my rigid cock between my upraised knees and feet flat on the bed. My asshole was greased up and eager for whatever additional abuse I was going to inflict upon it. And now my nipples were captured quite painfully with thick, heavy-duty clothespins.

"What am I going to do with you, you nasty slutboy?" I chided myself.

"Ummmm, you know what you like, you nasty whore...," I cajoled myself while pulling on the clothespins and stretching my tortured nipples.

"Oh god yes! Do it!! Twist those motherfucking tits you bitch!!!"

Pulling and twisting on my clamped nipples sent electric bolts of joy to my balls. My hips were pumping up and down with my hard-on flopping around, desperately seeking relief of any kind.

"Fuck! You nasty slut!" I whimpered, falling further into my abyss of licentious self-abuse.

"Get ready to be assfucked hard, you whore!!"

The pressure building in my balls felt soooooo fucking good, but I needed to forestall my orgasm again. Edging like this, I knew the payoff would be an otherworldly level of pleasure.

Perseverance won out as I lay there motionless with almost unbearable anticipation. Finally, I was ready to begin the final assault on my horny bottom. Leaving the clothespins in place on my nipples, I began to re-grease my manpussy with Crisco. Butter was oozing out of my hole from the quarter stick I had shoved up there earlier.

I was ready.

Swiping a fresh glob of Crisco on the now obscenely glazed cucumber, I positioned its tip against my wanton little knot. Slowly, I pushed the phallic veggie against my slippery rosebud, easing it past my sphincter

The nasty cuke was, indeed, a monster. I had selected it at the farmers market specifically for its length (around 11 inches, it looked like) and for its maximum thickness (around three meaty inches). A lewd boner had tented my pants as I shopped in the market for the perfect cucumber to shove up my ass. Nature boy, as I said....

I pushed on the formidable veggie cock and it began stretching my chute oh-so-nicely. It made me think back to the time years ago when I lost my virginity to Brian. He was quite well endowed! My initial struggle to accommodate his beautiful cock turned out to be life changing.

"Oh my! Your slutty hole hasn't forgotten how to take a big fat dick, has it?" I purred to myself.

The view in the mirror of my sloppy, puckered hole swallowing the beast had me light-headed. The steadily increasing pressure on my love gland made me squirm with delight! My dick was fully engorged with its bulbous head glaring an angry shade of purple. I pulled hard on one of my clamped nipples and twisted it for good measure.

"Geezus, oh my god, ohhhhhh yesssss," I groaned as my sphincter reacted by clenching tight around the outsized phallic invader.

"Oh god, I NEED to CUM so fucking bad! You're such a slut, you fucking manwhore...give your tight asshole what it wants, you bitch!!! Aaaahhhhhhh, yessss!"

Slipping into that state of almost intolerable tension before a massive orgasm....well, it was the pinnacle of excruciating self-abuse that edging freaks like me enjoy.

I rolled my hips upward, raising my legs high into the air, humping the cuke deeper into my welcoming rectum. My hole slurped up the cuke's thickness as it anally stretched me past any point I'd known before. The feeling of perverted fullness in my ass was pushing me rapidly over the edge. My eyes squeezed shut involuntarily while I was immersed in my depravity.

Suddenly opening my eyes to glance in the mirror, I was shocked to see my face, neck and chest flushed a sexy crimson red from my degenerate exertions. My tongue slipped out to caress my lips as I gathered my willpower to again delay my orgasm.... "oh.my.god..." I gasped as the cuke probed relentlessly up my ass.

My hips rose up to greet the stiff tormentor, and it felt like a good eight inches of hardness poking up my chute. My asslips and rectum were pushed open in a debauched gape at the widest part of the beast. Tunnel-vision closed in on me signalling that I was at the limit of delaying my release. The mirror showed my face was as red as if I'd sprinted a mile and there was sweat rolling profusely off of my brow...here was a man desperate to reach his peak of sexual agony and pleasure.

Grimacing with my eyes shut tight, synapses in my brain exploded with endorphin-saturated pleasure. Savage convulsions seized my prostate as the first excruciating wave of my orgasm washed over me. My slutty ass tightly gripped the nasty vegetable. I rolled my hips up as far as I could with my legs jerking whorishly straight up in the air. A more sordid display of mansluttiness I'd never seen!

Gasping for breath, time slowed and the massive wave of pleasure flooded my body. My entire face literally went numb from all the blood rushing to my cock.

When my lungs kicked into gear again, I hardly recognized the animal sounds that screamed forth from my throat.

"NnnnnnnnnnnAggghhhhhhh, fuuuuuuccckkk, fuuuuuucccckkk, fuuuucckkk, fuuuuuuucccccccckkkkkk! AAAAAAAHHHHHHHHHHHHHH!!! Fuuuuccck meeeeee!"

Hands clutching wildly at the bedsheets, my cock jerked violently and spewed forth thick white ropes of cum. Jizz splattered forcefully onto my face and chest, painting my eyes, nose and lips with salty ejaculate. The toe-curling pleasure was almost unbearable as my tortured balls emptied their steaming load.

My tongue snaked out, savoring the warm, salty spooge on my lips. The aroma and taste of cum saturated my senses as my orgasm peaked and crashed me against the rocks of wanton desire. Surprisingly, my mind was flashing back to memories of Brian flooding my ass with his cum and kissing me passionately as he assfucked me.

Holy shit!!...The cum exploding from my balls wouldn't stop! My hips spasmed, driving the filthy cucumber further up my ass and drawing more unhinged screams of passion from me.

Instead of my ejaculation slowing down to a dribble, the continual hammering on my p-spot brought on another eruption of sperm, splattering wetly onto my face and the pillow.

Through the fog of pleasure, it dawned on me that this was my first mind-bending experience with a multiple orgasm!!! Such a brutally continous endorphin release was the most powerful cocktail of pleasure I'd ever experienced. Floating on a wave of cum-drenched euphoria, I didn't want to ever come down. My eyes were squeezed tight against the flashes illuminating my brain, but my mouth was open in a silent scream as more ropes of salty cum splashed against my face.

I must've lost consciousness for a few seconds as the tide of indecent gratification enveloped me. There was a feeling of floating and, as my hand dropped away from holding the cucumber deep up my ass, the thick length of veggie violator shot out of my greasy hole onto the bed. Globs of Crisco mixed with butter queefed out noisily from my abused rectum as I purged myself of the deviant asslube.

Drifting in a euphoric haze, my entire body relaxed, except for my dick which was still hard as a rock and throbbing petulantly, cum dripping from the swollen head and down my engorged shaft.

Licking my cum drenched lips, I lay there in my own twisted squalor. The release had been so overwhelming that I had no strength left.

"Oh my fucking god..." I sighed blissfully... "Oh my fucking god...nnnnunnnhhhh... so fucking good.... so fucking gooooddd..."

"Geezus effing christ...."

Eventually, squinting through half-closed eyes, I again caught my own gaze in the mirror. My hand drifted slowly through the streaks of cum on my chest and scooped the ejaculate up to my mouth. Still warm, the tangy spooge tickled my taste buds. My cock slowly relaxed as I fondled it, squeezing out a remnant blob of sperm from my peehole. Massaging the slippery cum over my balls provided soothing after-care from the ravages of my playtime. I was in heaven watching myself in the mirror, stroking my spent cock and rubbing my cummy ballsack.

Spreading my knees once more, my eyes drank in the reflection of my now gaping anus. I adored the way my puffy asslips were trying to close up, having been so rudely stretched by the oversized veggie dildo. I slipped my hand downward to poke two fingers into my sloppy rectum. My dick jerked upward as I stuffed my fingers deeper into my bottom, searching out the love button on my hard little pleasure gland and pressing on it.

"Fuuuuuccckkk yesssssss, fuuuucckk yessss," I moaned as I fingered my wet hole. My hips rose greedily as I felt the salacious warmth in my ass quickly build again.

"Oh my fucking god, yessssss...more, MORE!...MORE!.....MORE!!! You nasty slut..."

Balls twitching while I panted like a trollop, I fingered myself to a surprising mini-orgasm. Cum drooled licentiously in a slow stream from my dickhole.

"Ohhhhhh, fuuuucckk meeeee, fuuuckkk meeee...nnnnnnuuuhhh....yessss," I gasped breathlessly.

I couldn't believe the unending pleasure that I was bestowing upon my body. As the mini-orgasm subsided, I used both hands to pull my asscheeks apart. The mirror revealed my gaping hole obscenely squelching out another gob of homemade lube.

Utilizing the rapacious cucumber, I scooped up the slick mixture draining from my ass and pushed it back into my abused hole. My hips involuntarily jerked again to ram my willing anus onto the phallus. With the heat of yet another mini-orgasm building, I lustily plunged the veggie shaft in and out of my butt.

Dragging the nasty playtool across my p-spot caused me to thrash around violently on the bed. Within a few seconds, another fierce bout of rapture overwhelmed me. I bucked the cucumber deeper, pushing another slow stream of fresh cum up from my exhausted balls to dribble lewdly from my dickhole..

How long could I keep this up? It was becoming a surreal dream of whorish self-depravity.

Groaning, I let the cucumber slip from my violated asshole. A decadent warmth permeated my rectum as I rolled over on my side. I was completely sex-drunk and saturated with perverted gratification. Sticky cum squished on my cheek as the side of my face hit the pillow. I drifted off with the words of Patti Smith running through my exhausted mind...

I'm dancing barefoot

Heading for a spin

Some strange music draws me in

Makes me come on like some heroine...

.............Not much later............................

"Sebastian! You're a mess!" exclaimed Kelly as she entered our bedroom.

Roused from my post-orgasmic daze I realized that my smoking hot girlfriend was home. I must've been quite a sight!

"Oh hi, baby! I can explain...."

To Be Continued....