tagTransgender & CrossdressersHigh and Low Ch. 11

High and Low Ch. 11


One could say Terry became Simon's first gay boyfriend. The muscular blonde drop in center social worker had taken the lost boy under his wing. He was giving him a degree of confidence it seemed. Very feminine, now thirty year old Simon, didn't feel so completely lost anymore. He was now well known at the West Holly Wood drop in center where he hung out. He was considered odd yet accepted. He'd saunter around in his jeans, t shirt and in his barefeet.

Yes, always barefoot. Very odd behavior in downtown LA outside of the down and outers. Simon was not really a down and outer though, and he was not quite as shy as he used to be. His thin slender feminine frame was a very, very sexy site to see, indeed for so many. It now gave him a degree of confidence he'd never had before.

He'd subtly unconsciously jiggle his curvy ass from side to side when he walked. His impeccable ass in his tight jeans making many a gay guy eye him wantonly.

Jessica, Simon's fifty something year old blond landlady, always thought Simon might be gay. For a long time she had wondered. Simon was always a very timid and rather meek guy. His feminine mannerisms, his ready lisp set off anybody's gaydar. Still, she was very, very surprised, yet pleasantly shocked the first time she saw Terry visiting Simon at the apartment.

Sexy Terry stood beside Simon, leaned into him, tenderly he ran his hand over Simon's cheeks, breathed deeply, pinched his nipples and then kissed him on his sultry lips. Jessica's face blushed red as she felt so happy for Simon.

"When did you realize you were gay?" she asked him.

"Oh, last year in Long Beach I had an experience." he shyly mumbled.

Simon and Terry's relationship had to be discreet though. It was a huge no no for a drop in community social workers to have serious relationships with the clientele, the "street people". Terry could be fired for this. Simon was definitely considered "street" by the Drop in center administrators.

Jessica would hear them having sex in Simon's room. Stripped naked, Terry and Simon would usually start passionate necking sessions. In full heat, cocks hard and upright. Simon would then be down on all fours on the bed with Terry in behind him, breathing softly on Simon's neck. Simon would feel Terry's mustache kisses on his ears, and cheeks and neck, and he'd groan in eager anticipation when Terry's thick cock entered him, and began pumping his ass more and more vigorously.

Jessica would hear the creaking bed, and Simon and Terry's moans and groans as the headboard of the bed would begin smacking against the wall. She would hear the joyous rising moans as they orgasm-ed. The massive creaking of the bed. Jessica would see them slowly walk out of Simon's room arm in arm and scantily dressed. Simon so serene and in near tears of Joy. Jessica felt so happy for him.

Most of the time, Terry and Simon would hang out away from west Hollywood. Maybe somewhere on Sunset strip or maybe sip some wine at an outdoor cafe on Rodeo drive.

"I think I love you baby, maybe we should get married soon". Terry softly told Simon once, grabbing his hand and softly pulling him closer to share Passion kisses. The intimacy always so serene. At long last Simon seemed happy.

One day shopping in a Sunset drive clothing store, Terry bought Simon some skintight bell bottom woman's jeans. The low rise showing Simon's slutty ass crack as the stretch denim looked painted on his sexy jiggling ass buns.

"I want them!" Simon had uttered excitedly,

A couple of very sexy sleeveless bare mid riff tank tops finished Simon's shopping spree and Terry and Simon went to a cafe to sip wine to celebrate. The sex with Terry was keeping Simon horny all the time now. He wanted to look sluttier and feel sluttier and he now did. They ended the night back at Simon's place with Simon near violently getting his face fucked by Terry's potent raging cock. Terry's cock pistol whipped Simon's face as it slithered and shot it's cum all over his face. Simon squealed and Terry aggressively moaned in sexual bliss.

"Such a bitch you are!" exclaimed Terry.

This had woken Jessica up, she just laughed when she heard this. "Have some breakfast boys!" she exclaimed knowingly the next morning.

One day Simon was quietly hanging out in the drop in center watching T.V. Relaxing on a sofa, looking slutty in his new tight jeans and purple tight tank top, and barefoot as usual. Various street people watched T.V with him. Junkies, hookers, the disenfranchised, you name it.

Simon was feeling good.

"How do you do? I'm Jaimers." Simon heard a voice. Very male but somehow effeminate.

Jaimers was sitting in a chair next to Simon. Simon's cock got very hard immediately.

Jaimers was about 5 '11, twenty seven, big and strapping and native Indian. He was rugged but effeminate. He wore his long hair back in a pony tail. He was thin but muscular. He wore a dark blue short sleeved cotton shirt and tight faded bell bottom jeans. He was barefoot just like Simon.

"I hate shoes too babe. I just got out of jail." he said, grinning. He had a notable lisp. He lit up a cigarette and offered Simon one.

"No...thanks." timidly replied Simon.

Jaimers went on talking about his drug addiction, his drunkenness, his jail time.

"I was a pimp. Boys and girls too. I'm bisexual, I don't hide it." he told a captivated Simon.

Simon really wondered, getting more and more curious about what Jaimers would be like, well, in bed. Simon was glad he hadn't seen Terry that day.

Simon and Jaimers left the drop in center together and slowly walked along the side streets. Close to a car park, Jaimers pulled out a rolled joint of Marijuana and lit it up.

"Here babe." said Jaimers exhaling the Marijuana smoke and handing the joint to Simon.

Simon took it apprehensively. He'd tried pot last year in Long Beach and later regretted it. Now he drew on the joint and deeply inhaled the smoke. In a few minutes Simon was high and feeling good. He eyed Jaimers with lust now. Staring at his cock and balls bulging under his tight jeans. The sensuality of his barefeet on the sidewalk heightened his feelings even more.

Jaimers pulled Simon close to him. He fondled Simon's sexy ass cheeks, then subtly, sensually played with his nipples. They stared lustily into each others eyes.

Soon they were climbing the rickety stairs of Jaimers's rooming house. The hallways were darkened and smelt like cooked cabbage. Once inside the small cramped room Simon was soon on his knees sucking Jaimers's thick torpedo cock.

"I'm your slut!" gasped Simon. His tongue rolling over the fat, juicy cock head.

Jaimers's cock whip lashed savagely inside Simon's mouth. Sometimes right down his throat, making Simon gurgle with delirious pleasure! He fondled the ultra hard cock and balls delicately. Sometimes running his fem fingers into Jaimers's ass crack and massaging his inflamed burning prostate. Simon swiveled on his knees in sexual excitement as he groaned and devoured Jaimers's 9 inches of manhood. Jaimers swayed above him, moaning with savage joy.

"Take it slut!" he exalted as his cock now twisted and turned violently inside Simon's mouth and down his throat.

He was now face fucking Simon at an insane pace. Simon whimpered with true submissive joy. He now fired his hot sperm all over Simon's face. His thick cock slapping his face relentlessly, getting in Simon's eyes and soiling his shirt. Jaimers quickly turned around, squatted like he were taking a shit, and grabbed Simon savagely by the hair and pulled his face into his asshole.

"Rim me slut!" He demanded.

Simon's tongue did rapid action in licking Jaimers's asshole thoroughly. Getting right up there repeatedly lapping at his Prostate. Jaimers's cock stiffened as he came.

"Fucking so good! You are one hot piece of ass!" exclaimed Jaimers, finally finishing ejaculating and now standing upright in front of Simon panting heavily.

Simon just giggled in agreement on his knees, slowly, gladly licking Jaimers's hot sperm from his fingers.

The night with Jaimers seemed to change Simon. It made him want to get wilder. He wanted to smoke pot as well.

Both Jessica and Terry noticed a change in Simon. He seemed really air headed and giddy sometimes, and his eyes were reddened.

"You aren't using drugs are you Simon?" Jessica asked him concerned, stroking his arm affectionately,

"No Jessica. I'm not." Simon lied.

Terry wondered but was naive. Very naive for a drop in center social worker.

Still, Simon would score some pot from a dealer at the drop in center and he would show up at Terry's pleasantly stoned. Pleasantly stoned, yet very, very horny.

"Fuck me raw!" he'd plead as Terry battered his cock into Simon's eager asshole.

Simon sucked Terry's cock with even more vigor as he knew he wanted to get much sluttier.

"Shoot it over me babe!" Simon shouted as Terry's cock exploded it's sperm all over his face. He cried tears of joy and laughter as he lapped up as much sperm as he could.

The taste of cum was always on Simon's mind. It felt so deliciously sexy cheating on Terry

One day Simon was walking the back streets of West Hollywood, resplendent in his slutty yellow tank top and painted on jeans, ass cheeks subtly swaying from side to side and ass crack showing so very seductively. He adored the feeling of the sidewalk, and black tarmac under his bare soles, as he strolled in the hot sun barefoot. He went into a discount store and bought a multitude of silver and gold and multi colored bangles, and placed them on his wrists.

He felt so slutty.

"Maybe I should paint my nails." Simon said to himself, his cock stiffening. "Oh God!" Simon exclaimed, his cock hardening even more, standing up through his jeans.

On a park bench sat the most gorgeous looking androgynous male Simon had ever seen. He or she sat with one leg crossed over the other, hot blue latex tights covering excruciatingly sexy legs. Toe nails painted silver as a flip flop lazily dangled from one foot. A black and silver zig zag sleeveless top, teased blonde David Bowie hair, blue eye shadow, and ruby red lips sealed it.

Simon ambled up to the bench, strolling sexily.

"I'm Angel. Sit down here please do!" the Queen said from the park bench, offering his beautifully manicured hand, long fingernails also painted silver. Eyes squinting suggestively.

Angel stroked his hand along Simon's tight blue jeaned thigh, sometimes catching and enticing Simon's cock and balls.

"Out for a barefoot stroll hey babe?" Angel said, eyes glistening sexily.

Simon just grunted in satisfied anticipation.

"God. I need a cigarette! You want one too?" Angel offered, reaching into his purse.

"Okay, why not?" said Simon breathless, taking the long white cigarette, putting it between his pursed lips while Angel lit it with his lighter. Simon's puckered lips exhaled a thick plume of smoke while they made erotic eye contact. Simon's cock pulsated wickedly when he thought about the idea of taking Angel to his place! Soon, the two were arms entwined, walking seductively on the way to Simon's place. Every so often they'd stop, embrace and share passionate slut kisses.

They walked as two lovers. Occasionally stopping and sloppily necking while limp wristedly smoking their cigarettes. As they came upon Simon's place Jessica was outside doing some gardening. She saw them.

"What!?!?" she said in shock. Her lower jaw near hitting the floor.

"Hi." Simon said dreamily, as their slutty asses glistened seductively as they walked like street whores up the apartment stairs.

"Who is that with Simon?" Jessica thought in a panic. "Simon doesn't smoke! Where is Terry?" She wondered.

They went into Simon's room.

"Just a second babe, I'll get an ashtray." Simon said, patting Angel's ass cheeks and then walking into the kitchen.

Jessica, now there, standing in front of him was at a loss for words. "Simon, when did you start smoking?" she asked.

"Oh, just last summer, Jessica." Simon quickly replied, his eyes sex glazed and in great anticipation.

"God, he's looking wild." thought Jessica.

Simon quickly entered his room. His Jeans were off in no time. He groped Angel who had unclasped his latex tights, and was now holding his pulsating nine inch she-male member. They had one last deep, wet tongue slut kiss, One last impassioned glare.

Simon quickly got on the bed on his knees.

"Do it! Do it! Do it! Do it! Angel!" Simon implored, shaking his ass back and forth, seductively finger his anus, his other hand slapping his hard, cock and balls.

"You are so on slut!" a belated Angel uttered, now in behind Simon, smashing his thick cock up against Simon's ass cheeks.

In one quick thrust Angel's prick slapped ruthlessly up against Simon's prostate, and again, and again and again! Simon's ass shook violently and he shuddered with joy.

"Fuck the new me please!" Simon begged in ecstasy when Angel's cock quickened speed, violently slapping against the sides of his Anus channel and then up against his prostate again!

"Oh! Hurt me Angel, please!" Simon moaned in ecstasy.

Queen Angel leaned over Simon, slapped his ass, then pinched his tender nipples, rocking Simon from side to side, his prick turning and churning inside his asshole. Angel's Cock head was repeatedly bashing up against Simone's prostate, igniting unbelievable sexual excitement!

"Oh babe! Oh babe!" Simon screamed impassioned, his ass gyrating wildly to Angel's quick thrusts.

Angel's fingers seductively massaged Simon's nipples. His pelvic area slamming up violently against Simon's sultry ass. The viscous prick injected him wickedly, mercilessly!

In and out! In and out! In and out! The thick cock head slammed into Simon's prostate!

The bed shook like crazy, they moaned and groaned loudly, as a plate fell and broke as Angel madly and royally fucked Simon.

"That's it Angel! Fuck me! Do fuck me!" Simon whimpered and purred deliriously, writhing submissively under Angel's sexual assault, both their cocks on fire and soaked precum wet!

Finally Angel shot his semen deep into Simon's ravaged asshole. It felt red hot and wicked as it shot into Simon's anal cavity. It charged like a mad demonic storm inside of Simon, madly peaking the sexual ecstasy! Simon's own cum shot out into his hand, through his fingers, and began drenching the bedsheets. Simon shook violently, and Angel above him too!

Angel held onto him for dear life with Simon dearly panting, taking in the fullness and impact of this mind blowing orgasm. They both shook uncontrollably as they cummed!

Jessica heard all of this. Simon had changed.

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