Shane's Shame

Shane's Shame

Shane always felt different. He had an attraction to men. He had always dreamed of a loving father in his childhood who would hold and guide him through life.

His mother was a strong, overbearing woman who demanded Shane's highest grades and best behavior.

As Shane grew older, his attraction to men and cross-dressing became stronger. Sometimes he would wear his mother's discarded underwear. He loved the silky feeling. It excited him.

After Graduation, he went to a medical college in Philadelphia. Out of the purview of his mother, it was there that he was able to seek comfort.

Shane had feminine facial features. With the least amount of makeup, he could dress and convince many to assume he was a woman. Shane would go clubbing in the city's nightlife as a young co-ed in girls' clothing.

He would avoid intimate situations out of fear. The fear of discovery and being labeled as queer or gay. He wasn't into the idea of having sex with men. He wanted comfort. He wanted to feel loved and desired.

Wearing women's silk panties would give him a massive hard-on. Often, he would have to jerk off to get his manhood to relax.

Shane knew he was playing a game that could become dangerous. Some men could become violent if they tried to grope him and got a hand full of penis.

He is aware that he has a nice-sized penis other men might be envious of.

His older cousin, Becky, once walked in on him after a shower and told him it was good, he was her cousin.

She told Shane if he was anyone else, she would jump his bones.

One night while he met a man who seemed nice. After a few drinks, he allowed the guy to kiss him. The kisses got more urgent. The man was groping his ass when he felt Shane's cock against his leg.

The man pushed him away and caused a scene. Outside the club in the park, Shane was crying. A guy sat down and comforted him.

"Hey there, my name is Bill." If you're going to dress up, you need to be careful. Many men will hurt or use you.

Shane and Bill became friends. Meeting for lunches or dinner and becoming close. Shane started to feel love for Bill. One night in the park, Shane leaned in and kissed Bill.

Bill returned the kiss. The kisses became more urgent.

He suggested they go to his apartment.

They spent a few hours cuddling and kissing. They slept in Bill's bed. Bill spooned Shane, wrapping his arm around Shane's waist.

Early in the morning, Shane awakens to the stimulating feel of Bill's mouth suckling on his ridged cock. Shane has never been sucked off before and blows a large load of cum into bill's mouth.

Feeling completely natural, Shane rolls onto his side while holding Bill's hand. Bill is still hard. He is rubbing his cock in Shane's ass crack. The pre-cum lubricating Shane's ass. Shane pushes back against the warmth of human contact.

Bill reaches down, adjusting the angle of his cock to penetrate Shane's virgin asshole.

Moving slowly and deliberately, Bill pushes his cock into Shane's ass pucker. Shane gets tense but Bill kisses and whispers he loves him.

Bill tells Shane to relax, as he reaches around taking Shane's cock in his hand, gently massaging it to a total erection.

Shane relaxes, and Bill sinks his cock in further. Lying there, without moving. Allowing Shane to become accustomed to the sensations of having a man's cock in his once virgin rectum.

Shane says, "wow, I feel so full."

Bill responds by flexing his Kegel muscles to send ripples of sensation to Shane's asshole.

Shane pushes back to force more of Bill's cock into him. They establish a rhythm of back-and-forth motion. Bill is now plundering Shane's ass as he continues to masturbate Shane's cock.

Reaching the pinnacle of sexual stimulation, Bill grunts, flooding Shane's rectum with his sperm.

Shane feels Bill's cum squirting into his asshole and reaches his climax, shooting sperm all over the bed as Bill's hand milks his cock of every last drop of semen.

Shane, cries, feeling the shame of his actions but knowing he loves Bill.

Shane laid in bed with Bill, sobbing as Bill comforted him with soothing words.

Bill was holding him, his softening wet cock against Shane's ass, his arms wrapped around him and said, "It's okay, I'm here"

Shane opened up, a flood of emotion pouring out in his words. How mixed he felt he needed to be with men, not women.

How he felt more female. He should have a vagina.

Finally, admitting how much he was sexually satisfied feeling a man inside his ass.

Bill listened and softly kissed him. Bill's cock was once again hard. Bill asked Shane if he would like to make love to him again.

Shane rolled on his knees, saying, "fuck me, fuck my shameless ass."

Bill got in position and said, "guide me, my shameless hussy."

Shane reached back, gripping Bill's cock and guiding it.

Bill pushed in, and Shane's asshole opened. Accepting Bill's rapidly advancing cock like a pro sissy slut. He fucked Shane's asshole hard and dumped another load into his bowels.

Again, Shane felt the warm fluid of Bill's cum filling his bowels and busted his nut, coating the sheets below.

After lying there in the afterglow, they both showered.

Shane and Bill became regular lovers. Shane admitted he preferred the part of the submissive partner. Shane also became an excellent cock sucker.

He learned the tricks of how to give just enough suction and tongue action to be rewarded with a mouthful of creamy male sperm.

Shane learned to swallow all of the precious sweet-tasting cum.

Shane now dresses exclusively in women's dresses. He has shaved off all his body hair, wears makeup, and often goes out with no underwear. He now calls himself Shanna and loves feeling slutty.

Shane's first multi-partner sex came about when Bill introduced Shane to Jim, a long-time friend of Bill's.

Bill assured Shane that Jim was clean and discrete.

Jim was a leading professional in the area with a family. Jim leads a very discrete dual life.

Bill and Jim took turns at Shane's ass and mouth. One would have their cock up Shane's well fucked asshole while the other was in his throat.

Shane loved it. His ass and belly were full of sperm. Both men had done a reach around, jerking him off twice.

Jim is now sucking Shane's cock. Bill, licks Shane's nut sack.

Shane fills Jim's mouth with his seed.

Upon bill's insistence, they both have regular HIV testing done. They only choose to have sex with the most discrete men.

One man, Rufus, is a large, very well endowed, very black man.

Bill had known Rufus for ten years. Bill had been telling Shane about The size of Rufus. Shane begged Bill to set up a meeting with Rufus.

Unknown to Shane, Bill was indentured to Rufus. Rufus loved white sissy bitches. Rufus was a pimp who traded in men and women.

They had to be clean, no drug users, no street whores. If any of his bitches got strung out, He would sell them to a pimp that would trade them on the streets for chunk change.

Bill and Shane were to meet Rufus at a gay club where Rufus set up a private viewing of him fucking Shane, his newest sissy bitch.

The room has audio and video equipment. People would pay to see Rufus break a bitch. Male or female.

That night, Shane wore a very short mini skirt and halter top. Having been formally introduced to Rufus, who glanced at him and said, "your one fine-looking bitch." Let's look at you.

Shane smiled and thanked him, turning around slowly in the bar.

Rufus reached out. Lifting Shane's skirt until his seven-inch cock came into view. Rufus looked at Bill and said, "damn, this bitch got some shit on her."

Bill replied, "yeah, and he wants to trade it for a pussy"

Rufus said, "I might be able to help, but you'll need to be willing to help me with my clients."

Shane asked how.

Rufus explained that his business serves well to do prominent clients that demand the utmost discretion. These clients pay well and tip well.

Shane listens intently.

Rufus suggests they retire to his private room.

Going into the room, Rufus pulls out his massive ten-inch ass stretcher. His cock is not only ten inches long but resembles a two-inch diameter black pipe.

Shane is mesmerized, scared of it, yet excited.

Rufus says to Shane, "why don't we start with some cock sucking."

Shane reaches out to hold the large black hunk of meat.

Rufus said, "that's it bitch, lick it."

Shane licks the mammoth cock from tip to base. He coats that beautiful black pipe with saliva.

Rufus says, "start sucking it bitch"

Shane opens his mouth wide to slip that cock into his mouth.

Rufus says, "bitch, get prepared to be skull fucked," as he grips Shane's head and plunges his cock in and out of Shane's mouth and throat.

Shane's lungs are burning as he tries to get air, tears flowing down his cheeks.

Bill leans in and coaches him to relax his throat and breath in when Rufus pulls back.

Shane relaxes, and his breathing is easier. He is rock hard from the abusive rape of his throat.

Rufus plunges deep into Shane's mouth and pumps jet after jet of potent black sperm down his gullet.

Shane's cock pumps a load of sperm onto the carpet.

Rufus says, "damn bitch you dumped your scum on my carpet."

Clean that shit up with your mouth while I stuff my black pipe up your Lilly white shitter.

Rufus positions himself behind Shane and pushes his wet saliva-coated cock into Shane's upturned ass.

Shane screams out, "It's too big!"

Rufus laughs and says, " bitch, you're getting your first real cock."

Rufus keeps up the pressure until he is balls deep into Shane's asshole. Then set a rhythm of sawing in and out while Shane licks his sperm off the carpet.

Rufus says, "Damn bitch got a tight asshole." I'm going to bust a nut in this white sissy boy's ass.

Shane was stroking his cock to keep up with Rufus.

Rufus plunges into the full depth of Shane's distended asshole. He grunts, unleashing his cum deep into Shane's bowls.

Feeling the flood of cum into his asshole, Shane panted, "I'm cumming," as he squirted his semen onto the floor again.

Rufus pulls his cock out with an audible pop and watches as the cum drips out of Shane's gaping asshole in front of him.

Shane drops to the floor, exhausted by the brutal ass fucking he received. Rufus left, after telling Bill, "I'll call you and the sissy bitch tomorrow."

Bill got Shane up and walked out of the room. For a walk of shame through the club and down the streets to their apartment.

Shane could feel the cum flowing out of his grotesquely stretched wet asshole.

Once they got home, Bill rammed his cock up Shane's asshole, adding more cum to leak out.

Bill said, "now you are officially a fucked cum-bucket sissy boy."

Shane giggled, "I guess I'm a real slut now."