Butch - Mike’s story

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Mike’s story - how he ended up under Jessie in part 1.
16.9k words
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Part 2 of the 5 part series

Updated 06/10/2023
Created 01/08/2021
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This one contains no gay sex. It does contain water sports and a little scat. It's tangentially related to the main story trying to relate how Mike ended up under Jessie. It's also my longest story so far and kinda deals with the relationship between Mike and Jessie.

So if none of that sounds like a turn-on or a good time then don't read it.

But if you have enjoyed any of my previous stories then please do give this one a go.

And please, please comment either way.

Mike's story

It wasn't easy being the younger brother of the high school football star.

Seemed like whatever I achieved, Max had already done and done better.

Even when I knew for a fact that Max never played guitar (which I did and did well) people would always tell me that my performance was good but it wasn't as good as that one time Max played the same song.

Or when a painting of mine was exhibited in the local gallery, it was good but not as good as that one drawing Max did. Even though I knew for a fact the only time he picked up a pencil was for a test.

Seemed like there were three choices open to the second son when your older brother is a star at school.

1.) Rebel. Smoke, drink, drugs and hang out a bad crowd. As fun as this choice looked it got shut down for me by Max's best friend Zak. Zak was already the school's hot, rebel without a cause and being my brother's best friend he kept a close enough eye on me so any bad influences knew to keep their distance. Or Zak, Max and half the football team would be paying them a swift, painful visit.

2.) Follow in big brother's foot steps. Join the football team, date a cheerleader, do well in school and be popular. Boring. And worse, forever in Max's shadow. Plus the constant accusations of all my success being down to big brother's influence.

3.) Walk my own path. Rebel in a socially acceptable way. Pursue my own interests free from the pressure of trying to live up to the expectations people had because of who my brother was.

I chose path number three. I followed my own interests, hence guitar, painting, swimming and dance.

I know. I know. Sounds like little brother is a closet case. But the truth is that to my teenage mind these were the perfect way to meet girls that either hated the type of jock my brother represented or had no interest in popularity by association.

So no fear of being judged by his standards.

And I was good at what I chose to do.

Swimming gave me good tone, definition and stamina. Guitar gave me good discipline and finger dexterity, not to mention the attention a lead guitarist gets.

And all the girls love a guy who can dance.

Life was one big win. I was carving my own path and looking good doing it. Big brother was busy being a jock so I was free to do what I wanted with no expectations.

Then Max started dating Jessie.

I had seen Jessie around, given that she was a cheerleader and big brother Max was star quarterback.

I had also seen her at some of my shows.

Short tartan skirt, torn stockings, cleavage proudly on display giving all the guys on stage the 'come fuck me stare'.

Safe to say some of my wilder fantasies involved Jessie.

Now she was dating my older brother.

Not ideal.

Especially after she started staying over.

Listening to your big brother having sex is awkward. Listening to him having sex with a girl you kinda fancied turned the awkwardness way past eleven.

Her moans were so fucking hot though.

Like barely had to touch my cock before exploding hot.

And soon I started jerking off listening to her moans as she had sex with my brother.

Fuck, she sounded like such a fucking hot fuck.

Then next morning she'd come down stairs in one of Max's football jerseys, even half asleep she had sexy 'come hither' eyes.

The fact that the jersey barely covered her delicious ass, she always seemed to smell like sex, like the way the too big top always ended up looking like an off-the-shoulder number exposing her slender and oh so kissable neck and shoulder.

Even the too cute way she tucked her hair behind her ear drove me crazy.

The way her nipples always poked out lewdly no matter what she was wearing was an undeniable plus.

Needless to say I was developing quite a serious crush on Jessie.

Besotted you might say.

Soon the only time I jerked off was when I was listening to Jessie moaning during sex.

It got to the point where I started to get a bit shaky and snappy with everyone if I hadn't listened to her moaning for a week or two.

I didn't think to record her moans, that felt too perverse, too creepy.

Better to listen to the real thing, it felt more respectful that way.

Even though I was a total asshole if I went for more than a week without it.

After their first big fight I moved heaven and earth to get them back together.

Why didn't you just start dating her yourself I hear you ask? Despite my increasing infatuation with her, she was dating my brother and I wasn't about to go piss on his parade especially with how heartbroken he was.

After I helped them get back together, something seemed to change.

Jessie still stayed over most Friday and Saturday nights, but the weeknight sessions stopped. Meaning I had to make the most of the Friday and Saturday night moans.

To compound my problem, the volume and frequency of her moans decreased as well.

Before the big fight it sounded like she was having the most incredible, toe-curling, brain-melting sex imaginable.

Now her moans were softer, quieter and usually just before the tell-tale sound of Max grunting hard and rolling off her.

Now that most of the band (myself included) were 18 we could play more of the bars around town and being pretty good we often picked up Friday and Saturday night bookings.

This was both a blessing and a curse.

Those weekend gigs were a total blast to play! They paid far better than the weeknight or opening slots we had been slogging through. The crowds were way more into it and the after parties could get pretty wild too!

Downside was no Jessie fix. Which meant that while I got my share of pussy (lead guitarist privilege) none of it turned me on as much as hearing Jessie's moans as she got fucked.

Which left me weirdly frustrated, I was having enough success with the girls so it took the edge off but I never got what I really wanted.

What I really needed.

Until one Friday night.

I had a gig but didn't feel like partying after, so I walked home, I let myself in quietly and headed upstairs. At the top of the stairs I noticed the bathroom light was on, I didn't think much of it as Max and I shared that bathroom.

As I stumbled towards my room, the bathroom door seemed to open just a crack, letting a little light spill out on to the landing and more importantly sounds.

I held my breath as I listened, it was Jessie! She was moaning quietly but in the still of the night it sounded like she was breathily moaning right next to me!

Instantly I was turned on!

Spellbound I crept closer, until I was as close to the slightly open door as I dared.

I said a silent prayer of thanks to whatever entity watches over teenage boys that I had chosen to wear jeans with a button up fly this morning. As quietly as possible, I unbuttoned my jeans and pulled out my cock as I listened rapturously to Jessie as she moaned her siren song from the bathroom.

I had my ear to the door now and underneath the stifled moans was the unmistakable sounds of fingers in wet pussy.

I nearly came on the spot!

My number one fantasy fuck was getting herself off!

This I simply had to see!

I couldn't resist temptation and peeked through the gap in the door.

She was the single sexiest thing I had ever seen in my life. Her eyes were screwed tightly shut in concentration, her mouth hung partly open, those bee stung lips glistening in the soft light. Her nipples looked painfully hard, one dainty hand was working her tit, the other was between her creamy, toned thighs, working her pussy, alternatively thrusting in and out, making those mind blowing squishy sounds then strumming her clit like speed metal solo. I watched awestruck as she bit down hard on the back of her hand as she made herself cum.

Wordlessly I came at the same time.

Unfortunately the sound of the dull thump as I slumped against the door in a blissful post orgamsic daze alerted Jessie and she opened her eyes. For a brief instant we held each other's gaze.

Sparks flew.

Staring at her in a mix of shock, embarrassment, lust, shame and complete and utter sexual satisfaction.

Helplessly I came again without touching my cock. Spurting another three or four ropes of cum in her direction.

It was the longest, most electrifying moment in my life.

Then shame and embarrassment overwhelmed me and I turned away, unable to look at her any more.

I felt completely drained and exhausted. I slumped down against the door, shutting it and smearing my cum against my back and hair.

I lay there dazed until I heard a gentle tapping at the door. I got to my feet unsteadily and hesitantly opened the door. Jessie had sat back down on the toilet, legs crossed, looking like Sharon Stone in Basic Instinct.

Except she was still visibly glowing from her orgasm.

"You made quite a mess Mikey" she managed to say in between deep breaths.

I couldn't meet her gaze so I stared at the floor, still red with embarrassment and guilt.

"Sorry." I muttered.

"Yes, you've created quite a little mess..." Jessie seemed to be talking to herself.

"I can't have you spying on me every time I'm getting myself off..."

"Even though I know you've been listening and jerking off every time I've had sex with your brother..."

"But... that was an incredible cum shot..."

"And your cock looks yummy..."

"And being watched certainly seemed to do something for me..."

"Trouble is... I'm dating your older brother... I'd say 'big' brother only... it looks like he isn't..." Confused, I looked up only to see her looking at my cock, which was getting hard again under her heavy lidded gaze.

She pushed her hair out of her eye and tucked it behind her ear in the way that always seemed incredibly flirty.

She looked me square in the face, with a mix of mischief, anxiety and lust(?)

"Well before we start getting ahead of ourselves, I'd better see if you're going to be worth the trouble..."

"See if you can keep secrets..."

Jessie looked up at me, biting her bottom lip nervously and blushing.

In that moment, she was so vulnerable and heartbreakingly beautiful and I knew I would die for her.

She seemed to recognise the devotion in my stare. She looked away coyly, blushed harder and smiled a little.

"On your knees." She whispered, still not daring to look at me.

I sank to my knees in front of my new goddess.

"Clean up your mess.." she whispered, her voice trembling.

This was the test, the real test. Everything up until this moment had been some sort of fantasy flirtation, now she had asked me - no - told me to lick my cum up off the bathroom floor.

(At no point did the thought occur to me to use a towel or even tissue paper.)

Slowly I bent down and tentatively licked at the cold cum on the tiled floor.

It was slimy and cold and bitter.

It had an aftertaste that burnt my tongue.

I licked again and again, slurping up the puddle of cum in front of my and licking the floor clean.

Jessie watched fascinated as I licked my own cum off the floor.

Finished with the puddle I crawled forward to lick up the ropes of cum, as I licked and crawled closer to the toilet I was glad of the weekly chore rota that included clean the bathroom floor and that this was my second load and so nowhere near as much or as thick as the first, which had splattered against the door.

My first shot had landed on Jessie's foot.

I looked up at her, the air thick with sexual tension. She looked back at me, she was so turned on I could smell her.

I was ready to cum again just from knowing that I had made her wet.

At least that's what I thought at the time, I wasn't able to comprehend that licking my cum off the bathroom floor might've turned me on. That such a humiliating and degrading act of submission might've got my cock hard.

She raised an eyebrow.

This was it. This felt like the point of no return.

Now or never.

If I kissed her foot we both knew I wouldn't stop there.

I looked up into her flushed face and whispered "please."

A smile flitted across her face, she shivered in pleasure and her eyes shone brightly. "Please what Mikey?" She purred softly.

"Please may I lick my cum off your foot?" I managed to whisper under her intense gaze.

She smiled again and nodded.

I bent down and sealed my fate.

I licked the spot of cum off the top of her foot.

I kissed her toes.

I kissed my way from her ankle to her knee.

Dear God.

Her legs were so smooth and warm and toned.

Her skin felt (and smelt and tasted) better than I ever dreamed.

She stopped me at her knee by pressing her other foot to my forehead and pushed me back until I sat on my knees before her.

She slowly dragged her foot down my face until her toes were at my lips.

We stared into each other's eyes as I opened my mouth and sucked her toes.

I moaned and closed my eyes as I sucked hard, drooling as the sweet, sweaty, sensual musk flooded my mouth.

My cock was hard and dripping pre-cum on to the floor as I lost myself sucking on Jessie's toes.

With an obscenely wet popping sound Jessie pulled her toes out of my mouth. I opened my eyes and gasped in surprise. She had that fucking sexy grin, her eyes we absolutely sparkling with lust and her lips were shining. She giggled at the comical expression on my face and swapped her feet over, I gratefully sucked her toes again.

Jessie moved her spit soaked foot to my cock and rubbed the head with her toes. I moaned in pleasure and thrust my hips up, wanting more. She giggled again, partly at my response to her toes against my cock, partly from my moaning tickling her.

She stroked the head of my cock and again I moaned around her toes, sucking harder now, trying to fit her entire foot in my mouth, licking at every inch of her that I could.

We started to work up a rhythm, every time she stroked my cock I would push my face forwards to take more of her foot into my drooling mouth. Like I was almost face fucking myself on her foot. Groaning constantly as she mercilessly teased my cock with her toes.

She was now rubbing the sole of her foot against the head of my cock, then using the pre-cum to stroke my shaft, then she would either press her heel hard into my balls, grinding against them or stabbing her bubblegum pink toenails into my cock. I winced at the pain but the abuse made made my cock harder and drool more pre-cum, which she would then rub on to the sole of her foot and start her delicious torture all over again.

Her heel crushing my balls was pure agony, her toenails stabbing my increasingly sensitive underside was worse.

I started to love it.

There was a twisted pleasure that started to grow along with the pain in my gut, it grew and grew and grew until I was no longer sucking at her toes, my mouth just hung open and I was panting like a dog, sweating and shaking, no longer in control of myself, just a mindless slave reacting to his mistress's abuse.

Encouraging it.

Wanting it.

Celebrating it.

Revelling it.

Needing it.

Jessie took her foot out of my mouth and wrapped both feet around my cock.

She stroked my cock with her feet, once, twice then with a silent howl of ecstasy I threw my head back and I came for the third time.

Or more truthfully, the first time. Nothing I had ever experienced came remotely close to what Jessie had just done to me.

If I thought I was hers before, there was no doubt in my mind now. The only thing on my mind was doing exact what she wanted, how she wanted, when she wanted it. And I swore to myself that I would learn her desires so well that I would service her before she realised what she wanted.

My life now revolved around Jessie.

There was nothing else in my life but Jessie.

My heart beat for her.

Wordlessly we looked at each other and I tried my hardest to let her know what I was thinking. She smiled shyly, like she understood and was flattered.

"Clean me." She whispered and I lovingly licked my third load of the night off her feet. Once I had finished I kissed each toe gently, staring into her eyes.

"Good boy" said Jessie.

We stayed that way for a little while, her toes in my mouth, just sharing the moment. I think both of us were coming to terms with what had just happened and knowing that it wasn't the end.

Jessie waited until I had come down from the mind blowing orgasm she had just given me. When she saw my breathing begging to return to normal and the fanatical gleam of devotion fade from my eyes she smiled and whispered "clean me."

She nodded down and I followed her until I saw her sopping wet pussy. I looked at her questioningly, she nodded more firmly and again looked down.

I crawled forwards as she adjusted her position, spreading her gorgeously tanned and toned legs wider. I kissed her inner thigh lightly, making her shiver delightfully. I kissed my way closer to her pussy and she moaned her encouragement.

I started licking her outer lips before I kissed just above the hood of her clit, then I licked her. She shuddered in delight and her hands left the toilet seat and entwined in my hair, pulling me forwards, directing me, guiding me, teaching me how to pleasure her.

Showing me all of her most intimate places, the ones that made her whimper and shiver. The spots that made her pussy gape open and closed, drooling juices.

She would occasionally murmur sweet words of encouragement, calling me a good pussy licker, an obedient clit sucker and best of all my personal cunt lapper.

I hooked my arms under her knees and took a tight grip on her waist, pulling her into me firmly, I started to concentrate all my attention on her clit, licking it with a quick rhythm, wanting to make my goddess cum.

The small bathroom was now filled with the sounds of my passionate licking and Jessie's deep ragged breathing as her climax approached. Her grip on my hair grew tighter, her panting grew louder and more sporadic, her face and chest flushed red, her legs which she had wrapped around my neck and shoulders started to loosen and shake. Her body gleamed with a sheen of sweat and her muscles started to clench. I kept up my pace I knew she was close, I licked her clit relentlessly over and over and over again, the sound getting wetter with every pass of my tongue.

Then she tensed painfully and screamed silently, the chords in her neck standing out like steel cables as the force of her orgasm swept through like a tsunami. I stopped licking and held her steady otherwise she would have lost her balance and fallen off the toilet.

I waited for her to stop shuddering and open her eyes. Eventually she looked at me a little sheepishly, grinning like the cat that got the cream.

"Fuck me! You're good at that." She giggled.

She groaned as I gently licked up her juices before pushing me away. "Too sensitive." She explained by way of apology. I nodded my understanding, still on my knees.

"Help me up."

I slowly stood, pins and needles shot painfully through my legs, I had no idea how long I spend on my knees worshiping her divine pussy. But judging by her 'just got royally fucked' glow, goofy grin and the fact that her entire body still seemed to be vibrating with orgasmic aftershocks, I must've been down there for a while.

I offered her my hands and helped her to stand, she nearly collapsed and I caught her, pulling her into me for a long, intimate hug.