Seeking Fulfillment

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Seeking Fulfillment
Seeking Fulfillment
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Year: 2024
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Aaron thinks he wants to be a girl. That is about to be seriously tested when the black neighbor boy catches him dressed in his sister’s school clothes.
Max Swan
  • Free Sample

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Thirty-year-old Aaron Wood was always a little different from his peers because, for most of his life, he took any opportunity he could to dress like a girl.  Now working as a yardman at a local college, living alone in his apartment off campus, Aaron spent much of his downtime in female clothing.  He still could not bring himself to come out as a transgendered female and wear female attire in public, but he was driven to find the person he really was.  To find fulfillment.  He dreamed of living the lady life—meeting a man, getting married, and all that.  Aaron was slim, five foot seven, red hair, green eyes with, pale white skin, and some freckles.

Over the years, he had accumulated a few items of female clothing. He could buy all kinds of clothes and lingerie online. However, if he ever got an opportunity to extend his crossdressing experiences, he would quickly seize on it without any thought.

To those around him, Aaron was a sweet and quiet man.  He got to know some of his neighbors since he lived in his apartment block, and they seemed to like him.  Often giving him a cheerful hello if they met Aaron in the corridors.  He even went to dinner at a neighbor’s house a few times, a single mom with two kids a few apartments down.  The Jackson’s seemed to enjoy his company, even though the recently turned eighteen-year-old college jock named Kyle wasn’t that fussed about him.

Kyle just considered Aaron one of his Mom’s charity cases.  The nerdy white guy who lived a few apartments down that didn’t seem to have any friends.  Kyle was a proud young black boy coming into manhood.  He was interested only in playing football and getting laid.  Aaron’s strangely effeminate manner just made Kyle think his neighbor was a fag.  His Mom was a real MILF.  An extremely attractive black woman with big breasts, long wavy black hair, and a curvy figure (big butt).  Rosie’s daughter was Marcia, also eighteen years old (she was Kyle’s twin), who looked like the younger version of her mother.  Only Marcia had to repeat a year in high school and was still there.

One night, Rosie Jackson invited Aaron over with an ulterior motive.  She was taking the family away during spring break for a holiday and wanted Aaron to watch her apartment.  More to the point, Rosie wanted him to water her pot plants and feed her goldfish and pet bird while they were away.  The Jacksons were going to the Grand Canyon for two weeks.  Aaron, a sweet man, quickly agreed, and at the end of the evening, Rosie handed him a key, telling the white man they’d be leaving in two days.

Aaron’s mind immediately thought of Marcia.  She was growing into an incredibly attractive young woman.  He had seen her going out all ‘dolled up’ on the weekends, lots of makeup, wearing truly short skirts and heels.  His mind instantly went to the thought of trying on Marcia’s clothes.  As luck would have it, Rosie was offering Aaron the opportunity to go into her apartment all alone while they were away on holiday.

*****

A few days later, Aaron watched the Jacksons depart for their trip away.  He waited for a day, then he went to their apartment and immediately made his way down the corridor to where he knew Marcia’s bedroom was.  It was typical of a teenage girl; there was stuff everywhere, and she had obviously left in a rush.  There were panties, bras, and tights strewn across the unmade bed and the floor.  A check in the family bathroom revealed a hamper, and in there were some deep brown stockings and a white suspender belt (these may have been Mrs. Jackson’s, but that was OK. She was quite a beauty).  Aaron’s dick was getting harder with every find.  It was soon reaching its full four inches of hardness.

He collected the white bra, heavily stained white panties, and the stockings and suspenders together, stripped off, and put them on without too much trouble.  He stuffed the bra with some other panties and was almost heady from the smell of pussy and piss.  The feeling of rolling the stockings over his feet and up his legs gave Aaron an even harder erection, and his dick rubbed against the moist staining, making him quiver with excitement.  He had seen Marcia’s high school uniform tossed into a corner, and he pulled out the short skirt and blouse and put them on.  Both the blouse and the skirt were a perfect size, and it was difficult to stop himself from jerking off and shooting his load.

Forcing the feeling down as much as he could, Aaron went over to Marcia’s dressing table and put some foundation on.  He struggled a bit with the eyeshadow and liner.  Still, the man did quite a reasonable job since watching YouTube videos on the subject.  Aaron penciled in some brows and a couple of layers of mascara on his lashes and decided he was looking hot.  He had reasonably long red hair and arranged it in a girly style.  With a dash of lipstick, a girl was looking back at him from the mirror.

In Marcia’s wardrobe, there were some lace-up high-platform ankle boots.  The heels are about five inches, and the platform is about an inch.  He put them on.  Carefully, he made his way into Mrs. Jackson’s bedroom, which he knew had a big, mirrored wardrobe.  When he saw the full effect, Aaron simply could not believe how good he looked.  He walked up and down in front of the mirror and generally behaved like a slutty girl, admiring his great legs.

Aaron returned to Marcia’s bedroom to change into another outfit.  He was just checking the dressing table drawers when a voice said, “Very nice.  You look hot, babe.”

His blood turned to ice.  As he turned around, he saw Kyle Jackson, phone in hand, grinning at him.  “The guys at college are going to love this, Aaron.”

Aaron stared at the black college jock wide-eyed.  “W-What are you d-doing here?” he stammered.

“I had a row with Mom.  I didn’t want to go on holiday with them, and she kicked me out of the car and told me to make my own way back home.”

“Err…  Oh well, I’m, err, oh shit, I’m sorry.  I’ll get changed.  Please, please, please don’t say anything,” Aaron said, feeling his cheeks burn.

He went to take the boots off.  “Oh no, you don’t,” Kyle said.  “If you don’t want anyone to know about this, you’re going to have to do me some favors first.”

Aaron really had no idea what the black teen meant but was desperate that his secret should not get out.  “What do you want me to do?” The desperation in his voice was palpable.

“Well, for a start, go into the kitchen.  There are some beers in the fridge.  Pour me one and bring it into the lounge, and be quick about it.”

“OK.  OK.”

Is that all he wants?  That doesn’t seem too bad,’ Aaron thought.  He did as he was bid and took the beer into Kyle, who was sitting in an armchair, having put some slow dance music on the stereo system.  He gave the smug guy the beer and turned to go to change.

“Oh no, my little sissy slut.  I’m far from finished with you!  Dance for me,” Kyle ordered.

Aaron loved dancing, and he had a repertoire of ‘girly’ moves.  He did as he had been bid.

“Nice!  Nice, baby.  You do know how to move, don’t you?”  All the while, he was filming Aaron on his phone.  After about ten minutes, he motioned Aaron over to the chair.  “So now you are going to show me what a bad little schoolgirl you are.  Kneel.  Give me your hand.”  Aaron knelt, and Kyle pulled the sissy’s hand towards his zipper.  “Get my big black cock out, you little whore.”

Aaron gasped.  “What!  Why?”

Kyle chuckled.  “Because you’re gonna suck it like a bad little girl.”

Aaron has seen enough internet porn to know that this happens.  ‘Oh my God, I’m gonna have to do it,’ he thought, feeling his stomach roil.  ‘I have no choice.’

“Please, not that.  I’ve never done that before.  Don’t make me do that,” the white man pleaded with the black teen.

Kyle smiled smugly.  He had the power here, and he knew it.  “Girl, I have loads of pictures and videos of you dressed in my little sister’s clothes.  Do you really want me to spread those around?”

“No, I don’t,” Aaron said red-faced.

He nodded.  “And do you want my mom and sister to know that the guy they trusted to enter our home was dressing up in their clothes and underwear to get some kind of sexual thrill?”

Aaron gasped.  “God, no.  I didn’t mean any harm, I promise.”

“Then suck my dick,” Kyle said firmly.

Gingerly, Aaron unzipped Kyle’s jeans and undid the top stud.  The bulge in his pants was huge, and as the sissy pulled them down, this great black cock, rigid as a flagpole, shot upright against his hand.  It was so thick and had large, throbbing veins around the shaft.  The head was circumcised, and the purplish/brown glans were already slick with pre-cum.

“Start by licking the piss split at the top.  Then work your way down,” Kyle ordered.

Oh my, this is horrible,’ Aaron thought, but he was trapped.  He could see no way out.  He lowered his mouth to the cockhead, and his tongue found the piss slit.

Kyle started moaning in pleasure.  “Ahhhhh…Mmmm…Yeah…Yeah…Good Girl…That’s it, keep going,” the teen moaned.

Aaron couldn’t believe it.  The taste was not as bad as he expected.  The slimy pre-cum was salty and clung to his tongue.  Aaron’s dick, which had deflated at the moment of discovery, was now hardening in Marcia’s smelly used panties.  He kept sucking on the head, concentrating on the piss slit.  Pre-cum would occasionally squirt into his mouth in a large glob.  As Aaron did the deed, he realized he actually liked doing it.  Kyle’s hands went to the back of the kneeling man’s head, and then he started forcing his huge black cock into the sissy’s mouth.

Aaron gagged.  He brought his hands up as he tried to push Kyle away.  “Urgh…  No, I can’t.  Please stop it.  I’ll choke.  Your cock is too big,” he begged.

“Oh no, you don’t,” Kyle growled.

From somewhere, Kyle produced a thin leather strap and, very expertly, slid a loop over Aaron’s left hand, then pulled it back behind the sissy.  He forced Aaron’s other hand back and wrapped the strap around it.  Now, he was powerless to stop the black teenager.

“Put your tongue right down,” Kyle ordered.

The sissy did as he was told.  This time as Kyle thrust his black cock into Aaron’s mouth, it actually went much further inside, butting the back of his throat.  The teen pulled out and said, “We’ll make a nice little cocksucker out of you yet.”

Aaron just gasped for breath, and then it came again.  This time there was a kind of ‘plop’ noise from his throat, and the cock slid right in until black hairy balls were touching his chin.  He pulled out and repeated this act several times.  When he pulled that long cock out, Aaron squealed, which seemed to amuse Kyle.  This went on for ten minutes as the black teenager face fucked the sissy.

“Right, girl.  Time to be fucked in that tight little boi pussy of yours,” Kyle declared as he pulled Aaron’s face off his cock.

Does he mean my asshole?’ Aaron wondered.  ‘Yes, he does.’

“Stay there, slut.  I need to get something.”  Kyle was gone about a minute.  When he came back, he had a bottle of lube.  He lifted the school skirt, and Aaron could feel him sniffing Marcia’s panties and his sissy slit.  “God, that sister of mine is such a fucking whore.  I can smell spunk on these panties.  She’s been at it again with that guy from three fifteen.  That dirty old fucker.  God knows why she fucks that dirty old pervert.”

That piece of information shocked Aaron.  The man in three fifteen was a fat older guy, probably in his fifties.  To think Marcia would choose to have sex with such a man was shocking.  ‘Mr. Davis,’ he thought with a shiver.  Aaron feared the man.  There was something so masculine and toxic about him, and it made Aaron feel nervous just thinking about him.

Kyle caressed Aaron’s stocking legs, cooing over how sexy he looked.  He kissed them from ankle to suspender, quite gently and lovingly.  When the teen got to the top of the stockings, Kyle pushed Marcia’s panties to one side.

“Wow, girl.  That’s a nice little clit you got there.  I like how you keep it all bald.  Seems fitting for a dick this small,” Kyle said.

The teen lubricated his fingers with lube and pushed two fingers into Aaron’s ass-pussy.  The sissy had been experimenting with various things like carrots and cucumbers, so Kyle did not meet much resistance from his sphincter.

“Ahhh… The sissy likes it in her pussy,” Kyle said mockingly.

Now, he had three fingers in and was moving them back and forward.  Aaron moaned gently and softly as the black teen lubricated his passageway.  After a short while, Kyle pulled them out, and the sissy felt his cockhead on his rectum.  Kyle was as hard as steel, and Aaron felt his anus part as the neighbor pushed very firmly into his little sissy hole.  The first attempt didn’t quite get in, but the second attempt forced his rosebud apart, and very gently, Kyle slid about three inches past his sphincter.  In a flash, he pulled back and then drove back in with some force, and not long after, those hairy balls slapped against the sissy’s much smaller nuts.

Aaron howled like a racing car off the grid.  Kyle laughed and pulled back and did it again.  The sissy lost count of the thrusts, and the teen was like a man possessed.  His big black hands were around Aaron’s waist, pulling Aaron onto his eight-inch black cock.  All Aaron could do was squeal and pant gently with each hard thrust.  The terrible thing was he liked the feeling of that cock deep inside him, and he pushed against Kyle to get it inside as far as it would go.  With every thrust, the sissy was becoming more and more a little cock whore.  The black teenager was kissing Aaron’s neck, his hot breath just a whisper away from the sissy’s ears, calling him a dirty slut, a slag, and his property.

Without warning, he pulled out and pushed the sissy over onto his back.  Aaron was gasping for breath and didn’t realize Kyle’s intention.  That big black cock appeared in front of his face, and before he knew it, the black teen let out a long moan, then a thick spurt of warm, creamy jizz hit his nose and splashed across his left eye.  This was followed by another jet that went straight into his mouth.  Further splashes hit his cheek.

“Oh no…  What?  What?  Urgh…  That’s disgusting,” Aaron groaned, screwing up his face.

He couldn’t believe what his younger neighbor had just done.  The jizz dripped off his nose and into his mouth, and the teen wiped his cockhead in it, pushing it over Aaron’s tongue, the cock tasting of asshole and jizz.  Aaron thought he was going to be sick.  Still, he wasn’t.  In fact, Aaron liked it.

“Better get used to the taste, you slut.  You will be doing a lot more of that,” Kyle said.  Aaron lay there while the teen took pictures of his face covered in sticky jizz.  “The guys at college will love these,” he laughingly said.

He lay there, looking at his stockinged legs, the ‘fuck-me’ high heel boots, his gaping asshole tingling, jizz still oozing from his mouth, forming a wet patch of it on the schoolgirl blouse.  ‘Is this what it’s like to be a girl?’ he wondered.  ‘Mmmm, nice.’

 

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*This eBook contains adults-only taboo erotica. All human characters in this story involved in any sexual behavior or acts are over eighteen. Any similarities to real people or real-life situations are purely coincidental and unintended. This eBook is 100% fiction, none of this ever happened in real life. The taboo themes of this story are fine for sexual fantasy, but only a fool would do them in real life. Do not try this at home. This disclaimer voids GW Enterprises Publishing Company against any claim that our stories have been a motivation for criminal activity. You are responsible for your actions. Thank you for reading this free sample.

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