Predator and Prey Pt. 18 complete

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Maybe.... maybe my brother Bobby. He's eighteen. Still in high school. Fucking cute kid! Thinks he's a hot shot with the girls! Damn cute though!"

"Bring me Bobby then. If you want drugs, bring me Bobby!"

"Fuck no! Not my brother!" he muttered. Though I don't know if it was from the fucking he was getting from Gus, or the thought of me fucking his younger brother and turning him.

As I was about to leave the room, Gus pulled Alice up and turned him around and sat him in the sling in the corner. Together we pulled the rope through the ceiling pulley and raised the sling to just the right height. Alice's legs were outside of the support ropes, so his ass was upturned and easily accessible. He was gaping, but only a bit since he was still a tight newbie. But his asshole was pouting, looking hungry to be filled.

As I left the room Gus thrust deep and Alice grunted and started swearing as he fisted his own dick, eager to cum, eager to have Gus seed him. I knew this wasn't the last time Gus would be fucking Alice.

I said good night to the bartender and to Brad at the door. I lit and smoked a cigar on my way home.

When I got home, I released my pet femmeboi Juanita from his room and let him clean up. I then took him to my bed and fucked him long and hard. He whimpered as my cock sliced through his ass. He had never fully taken to being fucked. He put on a good face at times, but was also very rebellious. Even if I had not met Carol-Ann and her beautiful son Taylor and decided to make him my next live-in sex toy, it would have been time to move Juanita on. I had gotten tired of him.

This was my last fuck with Juanita. Tomorrow I would deliver him to his new owners. He was destined for a boy whorehouse in Mexico. He'd get plenty of ass fucking there, whether he liked it or not.

But tonight I didn't just fuck him. I made love to him and made sure he screamed in pleasure the final time that I made him cum.

As I locked him in his room one last time, I wondered if I should look around for the jar that I had put his nuts in when I had castrated him soon after I had got him. He'd back talked or tried to escape one too many times, and to show him who was boss I had cut his ball sac open and snipped off his balls while he watched. I knew what I was doing, and did make sure he got proper treatment afterwards, but it did shut the little fucker up for awhile. His pickled balls were around the apartment somewhere. I guess I could throw them out now.

**********************

Friday had been an uneventful day for Kitten, at work at least. Of course, playing with David Axelrod before work had been fun. When he got to work, Kitten had moved the hundred dollars that David had given him from his bra strap into the top of his panties, where it was out of sight from the others at work. But throughout the day, he had constantly fingered the bills, getting an erotic tingle at remembering how he had "earned" the money. Fuck, he had gotten such a sexual charge out of teasing the lawyer, and then wanking him off! Each time he touched the money, his dick got so fucking hard in his panties. But he had not brought another pair with him so didn't want to splooge in them and make a mess he would have to walk around in for the rest of the day!

When Terry had given him his morning hormone shot in the ass, Kitten had wiggled his ass around sexily, but not sure if he wanted the older man's attention or not. But at the end of the day when Terry handed him his first pay, he kissed the shop owner on the cheek and giggled. The pay wasn't a lot, but it was enough for the type of work Kitten was doing now, just sweeping up and helping wash hair some times. Kitten had asked to be paid in cash, not for the tax concerns, but because he needed to spend some right away. He had decided not to spend the hundred dollars David had given him that morning.

Kitten was frustrated that his boyfriend Luis would not be picking him up after work. Yes, he now thought of Luis as his boyfriend, despite the large age difference, and the fact that Luis was his mother's boyfriend. And, he was a guy!

Just a month ago, Kitten would never have imagined the idea of having a boyfriend. He was a healthy young man, with a healthy interest in women, although he was mostly afraid to ask any girl out. But somehow, he found himself constantly thinking of Luis, and his wonderful cock. Luis treated him so well and in return Kitten found himself delighted to suck his daddy's cock for him and prance about like the gorgeous boy he was becoming. Yes, his daddy. Luis insisted that Kitten call him Daddy when they were together, and Luis treated Kitten so nicely that he could not refuse. And Daddy Luis had such a nice body for Kitten to press himself up against and kiss. Kitten LOVED being wrapped in Daddy Luis' arms and kissing him.

During the day Kitten took smoke breaks, sometimes alone, sometimes with one of the women who worked at the salon. For lunch, he had very little money and there had been no food in the house, so he had just gone to a corner store and bought an apple.

Before heading home after work on the bus, he had spent ten minutes in front of a mirror touching up his makeup and lipstick and brushing his hair, then spraying it to keep his sweep in place. He looked so fucking sexy! When he left the salon he lit a cigarette and smoked as he walked the short distance to the bus stop. He really wanted a joint, but decided to wait until he got home. His mother Carol-Ann had texted him that she would not be home in the evening, so he was looking forward to a long slow wank and many cums in front of his computer screen.

He got off one stop before his normal bus stop and went to a corner grocery store. He used some of the cash from his earnings to buy cereal, milk and other groceries since his mother was not buying any food these days. He also bough three packs of cigarettes, and a bottle of vodka for himself, and some orange juice. Luis had been buying him fruity drinks when they went out together and he was acquiring a taste for mixed drinks. When he could he would "borrow" from his mother's constant supply at home. But she was short on cash and it was possible her supply of booze might dry up some time. So he figured he would keep a bottle hidden in his room in case she ran out.

He knew his mother had pilfered some of his weed, so he kept a small supply of that where she could find it, but had found a better hiding spot for the pills and most of the weed that Luis had given him. He would also keep his ciggies and the booze in that new hiding spot, so that his cow of a mother couldn't find them.

As he browsed in the small store, he got a lot of attention from the couple of male shoppers in the store, and some puzzled looks from the women. He guessed it wasn't every day that they saw a tall young man, wearing a blouse and skirt, in hose and three inch heels and wearing full makeup and a radical haircut. When he paid, the check out girl was one of his classmates from school. "Taylor?" she asked, stunned at his appearance. But she didn't say much more than that and he sauntered out of the store, lit a cigarette, looked back at her and blew a kiss, then walked home.

At home, Kitten hid his smokes and booze away, the went to the kitchen and put away the groceries he had bought. He didn't mind sharing these with his mother. She had been right when she had said that since he was earning money he should help with the household expenses. But he was not going to just give her money. He would buy stuff that he wanted to eat. He got out her bottle of vodka and made himself a screwdriver, and then put some chicken nuggets in the oven to heat up.

All of this was still a bit awkward for him with his new longer nails. He had only had the extensions for a few days and so was still getting used to them. But they were painted bright red and looked so sexy.....

He got a joint from his room and smoked that while waiting for the food. For the next two hours he just relaxed with weed and another screwdriver and the food. He got some fashion magazines from his room and sat on the couch browsing those and watching youtube videos on the television set - mostly about fashion and makeup. But his mind kept wondering what Luis had in store for him the next day, Saturday. They were going back to the gay bar, Dante's, and upstairs to the Playpen, he hoped.

Kitten was eager to see his new friend Gordon, who was Daddy Blade's femmeboi. Daddy Blade called him Gordon to remind him he was a boy, but when Gordon was all girled up his girl name was Fuck Bunny! He had made out with Gordon a bit, making him cum. And upstairs at the Playpen was the first time Kitten had sucked Luis's cock, and Luis had jerked him to a fabulous cum while all the men up there had watched! Kitten was eager for a repeat of the experience, and much more!

Kitten could not resist playing with his cock any longer and went to his room. After stripping off his clothes, he went to his makeup mirror and refreshed his lipstick and touched up his makeup, especially his mascara. He was starting to get good at applying his makeup. He had learned to be patient even if it took longer than he liked. But the effect was dramatic. It was such a sexual thrill to look in the mirror as he jerked off and see just how girly he looked. Daddy Luis loved him being feminine and he loved and wanted to please his daddy!

Next he went to his stash of pills and took out an ecstasy tab and placed it under his tongue. Daddy Luis had told him he should use a tab each night. It would make him light headed and enhance his orgasms! He wouldn't have to think at all, just stroke and cum!

He plopped himself down in his desk chair and turned on his computer. Until not too long ago, he has spent many hours on many evenings playing online games. What a waste of time that had been, he now realized! Those games held no interest for him anymore.

One of the memory sticks Daddy Luis had given him was in the USB slot and he pulled up a couple of his favourite videos of older men and younger men making love with each other. Well, yes, some of it looked like love, but a lot of it was just pure hard fucking! It turned him on so much to watch cute guys sucking the hard dicks of older grey haired daddies, and in turn getting fucked hard by those men.

He had also started browsing porn websites, finding so much additional material to watch. He loved searching for pretty twinks, boys with lipstick and other terms that brought up cuties sucking and fucking with handsome hunky older men. Yes, he watched twinks with twinks and even young guys being brutally pegged with over sized strapons by young blonde women (they were always blonde!). It was all free and all so wonderfully sexy.

He was thrilled to watch his nipples and the flesh around them jiggle as he stroked his dickie with his long bright red fingernails, precum sliding down his dick. The female hormones were finally showing some effect and he knew that his tit flesh was growing. But there was a downside. As he jerked his cock, it wasn't getting quite as hard as it had in past. Oh, it would get hard; and it would squirt delightfully. But it took a lot more effort. Not that he minded. He loved looking at his stockinged legs, and looking at his beautiful face in the mirror, cigarette dangling evocatively from between his lips, as he stroked and stroked and finally tossed his head back and screamed as he jizzed. But it did take so much longer there days.

And much as he loved watching the mincing prancing prettyboys suck and fuck with the daddies in the videos, he was scared too. He had quickly learned that he loved sucking Luis's cock, but he knew Daddy Luis would want more. Daddy Luis would want to fuck him. Daddy had slid his finger inside of Kitten's ass when he had sucked Kitten's cock. Kitten had squirmed at the invasion, and eventually had enjoyed it. But he didn't want a cock in there. He liked being feminine. He liked wearing lipstick and makeup and stockings to enhance his beauty. He had always been a beautiful boy, he knew that, and now everyone else could see that. But he wasn't gay. Getting fucked in the ass would mean we was truly gay. And that was not him.

Was it?

He had to know.

He went to his mother's room. God, it smelled in there! What had she been up to. It smelled like... piss? He searched around and finally, under her bed, he found a dildo, and a harness. He discarded the harness and took the dildo back to his room.

This would be awkward on his chair, so he turned the computer screen so it was more easily visible from the bed. He put on a favourite video of two sissy femmebois with gorgeous made up faces being bent over a couch and kissing each other with lots of tongue while both were being fucked up their asses by large daddy cocks. The sissies panted and squealed in delight. It was a long video and suitable for the stimulation he wanted. He turned up the sound loud so that the squeals and lusty moans of the quivering sissies filled the room!

Kitten grabbed his bottle of lube, lay back on the bed and spread his legs wide. He squirted a lot of lube on the head of the dildo and then lay it to one side. He poured lots of lube on his fingers and probed at his asshole, spreading the liquid around his anal pucker, and then trying to push some inside his ass. His finger met strong resistance, and the angle was all wrong, but he finally got his finger in his ass up to the first knuckle. But no further.

It was frustrating. He enjoyed when Luis fingered his butt hole, but even that took some effort by his daddy. He didn't want anything larger in there. Really he didn't! But he knew Daddy Luis would want to fuck him. He was amazed that Luis hadn't tried to do so yet. Would he enjoy it? Would he even let his boyfriend fuck him? He wasn't gay! He didn't want to be fucked. He didn't want a cock in his ass!

But.... he had to know.

He jerked his cock a few times. It was semi erect, and he wanted to jerk it even more, but he only had two hands. He needed both of those to grasp the dildo and place it against his asshole and he pushed. If his mother had been any normal mother, there would have been carrots in the refrigerator, and he could have tried using the smaller stiff pointed vegetable to penetrate his asshole. But no, his bitch of a mother had to be a drunk drugged out slut who had no regard for her son needing a carrot to fuck his ass with! He giggled at that, and tried to push the dildo into his ass. His ass resisted. The head of the dildo was too damn large for his tight butt hole!

After several minutes of wiggling the dildo and applying pressure in various directions, he gave up. He stood up and moved to his chair. He steadied the dildo upright on the seat of his chair and turned around. He lowered his ass until he felt the dildo against his asshole and tried to lower himself onto it, to force it into his ass. But the slick lube caused the head of the fake dick to glance off in one direction or another. When he finally got the head pressed directly against his hole and pushed downward, his ass would not open and a bit more pressure caused the dildo to bend slightly, lose its position and go flying off towards the bedroom door!

He couldn't do it. He couldn't get the dildo into his ass. It was a sign. He wasn't meant to take a cock in his ass! Luis would just have to be satisfied with kissing him and cumming in Kitten's mouth after a good sucking. And Kitten had discovered he enjoyed sucking his Daddy's cock. He would keep Daddy Luis satisfied that way!

He wasn't gay. He just liked to be a very pretty boy who would suck a cock for his Daddy. He would get himself a girlfriend as well. Perhaps Melissa. But someone he could fuck. He had lied when he had told Luis that he had had sex with a few girls during highschool. Yes, he'd been on a date or two, but he had been too introverted to make any moves on the girls. He'd never had sex with a girl, beyond a simple kiss, if that counted. He had never put his cock in a pussy. Never had it sucked, until Luis sucked him!

He liked being pretty. He liked teasing men. He looked over at the hundred dollars on top of his dresser and giggled at how easily he had taken that money from David. Yes, he definitely liked teasing men. But he would never let a man fuck him!

He got up and adjusted his stockings. He put on his heels. He lit a cigarette and stood in front of his full length bedroom mirror. He slowly wanked his dick, turning this way and that way, enjoying his reflection in the mirror, and imagining David Axelrod, kneeling in front of him. A straight lawyer with two grown sons. With a wife. But on his knees in front of Kitten. Because Kitten told him to. David Axelrod with Kitten's cock in his mouth.

Kitten quickened his jerking, his long fingernails stroking up and down his cock. Fantasizing what might be, what he might do with David. What he might do with other men. Mmmmmm. His mind spun with the possibilities.

Yet, just as he could feel the cum pumping out of his balls, and then spurting high in the air and his fist flew up and down his cock.... just at the moment he came... his fantasies turned to Daddy Luis standing behind him, thrusting his cock into Kitten's ass, and fucking him hard. That was the image in his mind as he spurted his jizz.

Oh god, he thought, I don't want to be fucked. No!

But.....

********************************

Hello luvvers,

Well, here we are with Chapter 18. It seems like each chapter is longer than the previous, mostly because the plotting becomes more complex and the cast of characters grows.

The first part of this chapter has already been posted as Chapter 18a. This posting includes that previous posting.

Chapter 19 is going to be the next big event chapter, focussing mostly on Kitten, and featuring a return to Dante's and the Playpen upstairs!

One thing you could help me with please. In this chapter I have given Luis the last name of Grande. I think I gave him a last name in an earlier chapter, but I could not find that. If you come across that last name please let me know and I will revise the mention in this chapter for consistency.

Speaking of which... this story has grown beyond anybody's expectations when I began it. This began as an extension of my earlier story Sissy Candy in which we met a version of Kitten who was about two years into his feminization. I no longer feel compelled to match this version of Kitten to the one mentioned in the Sissy Candy story.

Please enjoy and as always, leave comments about how much you love the story, or if you think perhaps it has strayed. I do love to read your speculation as to where the story may go, but I do know where the path leads and how our pretty femmeboi is going to follow that road.

And believe me, I try to get these chapters out to you as quickly as I can. However, real life does get in the way, or sometimes clears the path for a more speedy posting.

I look forward to teasing you much more very soon.

Keep those flag poles stiff in the breeze!

Love,

Mistress Tawny

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
24 Comments
AnonymousAnonymous2 months ago

Actually, it is now almost TWO FULL MONTHS since the last chapter posted. Yes, life gets in the way sometimes, but I have a bad feeling about the future of this story. A damn shame too, as the two most anticipated chapters were up next.

JohnNhoj0000JohnNhoj00002 months ago

Can't wait to see the next chapter! Please keep them coming! (Pun unintended)

AnonymousAnonymous3 months ago

Closing in on a full month since last posting. Looking like another long wait like Nov'Dec.

AnonymousAnonymous3 months ago

Kitten is by FAR my favorite character. By FAR. The sections when she appears are the highlights of every chapter. Hoping the next post is coming!

AnonymousAnonymous3 months ago

Focus more on Kitten and Lois, and their intentions and emotions. Of course on Carol too. No need to overcomplicate other introduced characters, i know you think it is a great idea to introduce alen, his brother, gus etc. but they are not as important as Melissa who everyone here wants to see introduced here as a new tool for something. Also, dont make a simple gangbang out of Kitten's first time, it is supposed to be intimate as possible.

Show More
Share this Story

story TAGS

READ MORE OF THIS SERIES

Similar Stories

Sweet Baby 01 Timmy meets his shemale pornstar parent!in Transgender & Crossdressers
Build-a-bride Sophie waits for her hubby by the door, and reflects...in Transgender & Crossdressers
How Our Cuckolding Started, Pt. 01 Wife discovers husband's bbc cuckold fantasy.in Loving Wives
Mommy's Morning Milking It's morning. Your Mommy Mistress is going to milk you dry.in Transgender & Crossdressers
The Fetish Shoe Shop family Visit Steven and his slutty mum and dad visit the fetish shoe shop.in Erotic Couplings
More Stories