High and Low Ch. 05

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Sliding over the edge and falling into temptation.
2.4k words
4.18
23.5k
6

Part 5 of the 11 part series

Updated 11/01/2022
Created 05/02/2008
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Simon and Brenda's sex life definitely picked up a step. She began using strap on dildos on him. Fucking his ass raw while he squealed in delight.

"So you want to be a fag boy! " she would admonish him, as he grovelled on all fours. Brenda battering him from behind with a fury so very unrepentant.

He would swivel and moan in glorious delight. The double action of the Dildo also playing as a maniac exciter of Brenda's own very hot, very dripping wet pussy.

"Oh Baby, Fuck me! " he'd squeal as Brenda's thick shaft probed and worked magic on his erroneous zone. Ripping into his asshole with lust galore. This woman rode him hard.

"My little slut! " she'd hiss in his ear and lean over him, and maybe love spit him. She'd often lean back and hard slap Simon's exquisite ass.

Her fingers titillated his nipples and boy breasts. Her hot breath, passionate on the back of his neck. He played with a delirious frenzy with his own stiff upright penis.

Just to think he was so recently a virgin! Just helpless cherry!

They'd collapse in a soaking, shuddering entwined mess, as they simultaneously Orgasm-ed, coming to their full mind blowing climax in unison.

So very together as lovers and sex partners, lying together in their wet bed of sin.

They would soon recover from the sex and go back to stroking and kissing and caressing each other, and sipping their sweet California wine.

"I love you baby, you're my barefoot slut. " Brenda would giggle and purr. Brenda the Dominant she master. Simon the submissive sissy slut.

All So very pleasant and in love. Which is what Brenda wanted. A real relationship.

Someone steady to come home to who loved her. Someone whom she loved back. Someone she could grow with and Someone she could look after, if needed. Someone like Simon.

Simon was there.

On nights when Brenda was working though, Simon got so very bored, staying at the Long beach apartment by himself. Some nights he caught the bus to some of the long beach dance clubs.

He always went barefoot. Always getting sexually turned on when this raised eye brows, Which it often did. It made him blush.

He carried sandals in his shoulder bag, just in case any of the clubs policies were infringed upon. He just loved going barefoot, just as he loved the feel of the tight low rise denim on his ass. and the skimpy feel of his halter top. The way his bangles would shake around his wrist, so very, very feminine. The cheap rings he wore!

He'd get mildly inebriated on wine. He'd mostly listen and sway to the clubs pounding techno, and underground drum and bass and avoided other people. That's what Brenda seemed to want him to do.

Sometimes Brenda even wanted him to wear shoes!

Brenda cared about him though. The credit card she gave him paid for everything and she was very generous. So why shouldn't he go out to the clubs by himself sometimes?

Lately he didn't even feel like dancing as much. He found he was thinking of cock a lot for some reason. God, he wanted to try it, but Brenda? Brenda outside of their sex life, would only talk about job security and maybe buying a house. Gay sex was a taboo.

God, Simon was confused. He was also drinking just about every night now. Many times when he was really getting a nice buzz on, he opened up in conversation to other clubbers. Straight, gay, bisexual, transsexual. Who cared?

Many sexually excited him. He always had to leave early and get back to see Brenda though, since her nurse shift would end early.

How could he overcome the shyness? The loneliness?

On the nights Simon and Brenda would go clubbing, they were now often joined by Brenda's co-worker, fellow assistant nurse Farrah, and her boyfriend Miguel.

Farrah was another former party girl who had changed gears and had now decided to focus on a career instead. She was twenty seven. Simon liked her better than Brenda's other friends.

Greatly respected at the hospital, Farrah looked quite the spike heeled slut when she partied though. Her long ginger blond hair teased and tossed.

She wore way too much makeup, and had long painted finger nails, and wore the slinkiest, sleaziest dresses you could ever imagine.

She'd light up long white menthol cigarettes, much to the chagrin of Brenda.

"I know I should quit, but I only really smoke when I drink now, darling. " She would defend herself, dragging on her cigarette so elegantly, and exhaling plumes of smoke that danced and drifted across rooms.

Brenda didn't really care. Farrah had become perhaps her best friend. She was certainly a lot of help at work, be it in the wards or for study assignments, and no, she didn't smoke at work.

Her boyfriend Miguel was a thirty five year old tall, dark, slim but muscular , Latin American with a trim mustache.

He liked dressing in black, be it tight black jeans and t-shirt or elegant evening wear, whatever the function, he was stylish and up for the occasion.

He worked as some kind of assistant in a travel agency. He moved quickly and gracefully Simon noticed.

He moved like a minx, and talked like a fox, and if anyone had gaydar, Simon certainly did.

He was rather pleasant upon first meeting Brenda and Simon.

"So pleased to meet both of you" he said, his eyes seeming to fixate on Simon for just a little time longer than normal.

Brenda didn't seem to notice. Simon felt that old apprehension returning as somehow his cock got harder. He certainly noticed.

Miguel definitely liked to drink.

"I like this dance music, but I also like to move to a Rumba! " he enthusiastically declared to them in a club one night. His thick, South American accent slurred after more than a just a few Margaritas.

"My god Simon! You look like a bisexual dream! We should visit the Panama club, and see the drag queen show! " Miguel once implored them as they all sat at a table.

Simon didn't know what to say. though it turned him on, he just blushed while Brenda just stayed poker faced.

"Oh you never stop! Bisexuality is so fucking sexy! " Farrah enthused playfully, laughing, brushing Miguel's arm with her fine boned, sexy fingers.

"What he means Simon, is you have a beautiful androgenic look. " Farrah intoned, looking more beautiful than ever.

Her red painted lips drew on her cigarette seductively . She sensually blew out streams of smoke, visually akin to cascading feminine fountains of light. Hot and sexual.

One day, some time after, one humid afternoon, Brenda, Simon, Miguel and Farrah all gathered together for a barbecue at Farrah's house. It was Brenda's idea to have a Barbecue.

Farrah insisted on hosting it though, She'd make some of her killer Mexican chili.

They had just poured the first wine and margaritas when simultaneously, loud beeps emitted from Brenda's and Farrah's handbags.

"Fuck No! I don't believe it! " Cursed Farrah!

Brenda and Farrah were both on emergency hospital call, though they both hadn't been called in a year!

Simultaneously again, both of their cell phones went off.

"Okay Norah, see you shortly. " said Brenda into the phone rather disappointingly.

Farrah acknowledged the same. A main plumbing line had broken at one of the hospital wings. Brenda and Farrah were both needed immediately to supervise shifting of patients, supplies and whatnot to other parts of the hospital.

"Okay babe! See you some time tonight, " said Brenda, kissing Simon.

Both girls busily turned away. Impossibly sexy denim ass cheeks bounced, swayed and swished, much like a hookers dream, and the last Simon and Miguel saw of them.

They left in Farrah's Camero.

"Well babe, I guess it's just me and you. " whispered Miguel to Simon, as he then sauntered back into the house.

"Wow! He called me babe! " Simon realized as his heart began beating rapidly.

Surprised, Simon's cock got rock hard and his bare feet slowly began stroking the patio concrete in anticipation. He downed another glass of wine, and began getting tipsy.

When Miguel came back outside, he was wearing black tights, and a thin black sleeveless mesh top. He oozed sex appeal beyond belief to Simon, whose mouth just watered.

Miguel wasn't wearing shoes either, and his toe nails were painted black!

"I thought I'd go barefoot, just like you, " he told Simon breathlessly, leaning over, purposely showing Simon the most incredible ass.

His curvaceous cheeks almost in Simon's face. as he lit the barbecue.

Simon sat down on a lawn chair and sipped more wine. Openly, visually lusting after a man for the first time in his life. He didn't know why. Maybe it was because of the wine, but right now he just didn't care. He knew he looked turned on and didn't want to hide it.

Miguel then sat down directly across from him, putting his feet on a small table that was between them.

He eyed Simon passionately. He rubbed his thighs.

"So Simon? You ever have sex with a guy before? " asked Miguel.

Simon was hesitant for a few seconds. They could hear the neighbors. Simon desperately thought the time is now.

"No! No yet, but I want to! " he loudly blurted out.

Simon had now admitted this to another guy! And to Farrah's boyfriend as well! He felt the throbbing in his crotch. God, he felt excited!

He began rubbing his own thighs.

"And you? " asked Simon.

"Oh, I've been a total slut. I've been with hundreds of guys! " laughed Miguel.

"Oh Farrah knows, but she's real Vanilla now, much like Brenda. She wants a relationship. What she doesn't know won't hurt her though. " said Miguel slyly.

They both took a sip of wine. Miguel then pulled out a metal pipe and quickly lit it up, with a plastic disposable lighter.

Simon recognized the smell of marijuana. Miguel inhaled deeply, then exhaled and then offered it to Simon.

"But, I've never smoked it before, " he said.

"Oh Come on! It's only pot! It'll make you feel good babe! Try it! " said Miguel enticingly. Simon's cock got even harder.

"Well okay, " said Simon, taking the pipe and inhaling. It turned him on when somebody told him what to do.

"That's it! Hold it in! " Miguel guided him, as Simon tried to avoid coughing out the Colombian drug.

They did this several times. Simon enjoyed the sweet taste. He'd been wanting to try it for awhile. Slowly he began to feel light headed, with a warm glow . The atmosphere now felt electric.

His senses seemed much more, well, sensitive! Even more now, Simon wanted to submit to this horny stud.

"Maybe you can be my queen! " Miguel exclaimed, thrusting his barefoot onto Simon's crotch.

Simon grinned, and began stroking Miguel's black nailed toes and souls, as he felt the ball of Miguel's foot on his throbbing prick.

"Come on babe! " Miguel said in sexual heat, standing up, and grabbing Simon by the hand. They began fondling each other.

Arm in arm, he led Simon into the house and into the dimly lit back bedroom. Farrah and Miguel's bedroom.

Sexy Latin dance music filled the room from a stereo. The incense smelled like a whore's house.

Standing in front of the bed, they both embraced and began necking with each other. their tongues manic and athletic, in unison with their throbbing cock and balls.

They were both feeling up each others ass and genital area as the passion kisses got more feverish and fervent. The music seemed to get louder as their hornless increased.

"So this is it! I'm gonna be a gay slut! " thought Simon wickedly as they made out.

They both fell back on the bed.

"I wanna suck your cock! " exclaimed Simon, now drowning in hot sweat, both his and Miguel's.

Slipping off his tights. Miguel sat on the edge of the bed, his thick ten inch cock, all red and upright, he stared hungrily at Simon.

"Teach me how! " pleaded Simon like a needy sissy, getting on his knees and then throwing his mouth onto the head of Miguel's prick.

His tongue began slurping at a rapid rate. His right hand fingers began working Miguel's balls instinctively.

"That's it tart!" enthused Miguel breathlessly, almost shouting, both of them shaking in the heat.

Simon had loosened the clasp of his own jeans and was playing with his own solid, stiff cock throughout all of this.

"Oh baby!" He managed to utter. Miguel's cock rammed against the back of his throat,

His tongue swished around the rod at a frantic pace. Miguel's slut hands fondled Simon's upper torso and breasts.

Simon was finally doing it! Finally sucking cock! He felt so submissive and used. God, he loved it!

He wanted to take the cock right down his fucking slut throat as he lapped at it! God almighty, he tried.

Finally, Simon nearly chocked as Miguel's thick, hot sperm shot down into him. At first gagging him and then sliding down his chin and onto his body. Onto his own hand and cock.

Simon exploded in ecstasy. His own sperm then shot out, mixing in sticky puddles, with Miguel's sinful juice.

"I'm a fucking whore! " exclaimed Simon.

They both played with themselves as the climax simmered down. They eye balled each other in insane lust. Simon wiped up some of the sperm mix with his hand and licked it, giggling, staring straight into Miguel's eyes.

Simon stuck out his sperm stained tongue at Miguel, and they had one final kiss. One final tongue wrestle taste of they're deviant endeavor, before they finally, lay back and relaxed.

"You slut!" said Miguel, playfully admonishing Simon, with one barefoot resting on Simon's ass cheek.

A few minutes later, in Miguel's living room, Simon began feeling restless, then over come with paranoia. What had they just done?

It was crazy!

Slowly it dawned on him!

Why?

Brenda would not be pleased!

And why did he smoke pot? It was Miguel's fault!

"You won't tell Farrah or Brenda, will you? About us? " Simon pleaded.

"No I won't Simon! Just relax. It'll be okay! " Miguel assured him.

Still not convinced, Simon called for a cab ride home. He was completely paranoid and depressed for the whole ride. He hated himself.

When he got home Brenda still wasn't there. Simon went straight to bed and to sleep.

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3 Comments
SomehowyouSomehowyouover 14 years ago
Well written

Bisexual you are truely a talented writer. Whether someone is Bi or not I think they would appreciate your style.

Fatwa_MorganaFatwa_Morganaover 14 years ago
Great continuation

This is a perfect continuation of the story of Simon and his sexual evolution. The author is doing a great job of maintaining the integrity of his story. I loved it!

Calit69Calit69over 14 years ago
It had some potential

as a rather simple story and then went completely south with an abrupt ending. Fascinating how the sissy boy suddenly develops a conscience but previously would go clubbing. Not the most graphic or sexy story

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