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This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up.
Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol’s bitch forever?
We pick up right where we left off. Andy, now dressed in drag stared at his dominatrix crush Riley, who was very perturbed to say the least at this boy exposing himself to her in front of her apartment door, technically in public.
We’ll backtrack quickly on Andy’s outfit. It consisted of a frilly black midriff, with detached skin tight black and white striped arm stockings, a very short frilly black skirt, black and white striped stockings, and black high heels. Rounding out his look was some makeup and a long black wig, perfectly covering up his short haircut. He of course had on a stolen pair of Riley’s panties which were now pulled down to expose his cock, locked in a cock cage.
Riley was not surprisingly mesmerized at the sight in front of her. This was quite possibly the last thing she expected to see knocking at her door, despite her being a dominatrix who relishes in this sort of thing, she was nonetheless disturbed that this crossdresser…or was it a trans person? Andy was so passable Riley couldn’t tell, but anyway she was disturbed by the fact that Andy merely stood there exposing himself completely unannounced.
With a quick kneejerk reaction, Riley pulled him inside. “W-What? What—what—who are you, come inside before the fucking cops get called, Jesus!” she looked to see if anyone noticed, they didn’t; and she slammed the door behind her.
“What the fuck is wrong with you—who are you?” she asked.
“I’m Bianca” Andy retorted.
“Yeah-yeah I heard you. What’s your real name?”
“I told you, Bianca” he retorted.
Riley rolled her eyes. The twenty-three year old did not need nor want this, especially considering Andy seemed to be this weird sissy robot she didn’t ask for. Yet, still, she was nonetheless intrigued that someone would go to all this trouble to just brazenly show up at her doorstep practically begging for a pity fuck. Part of Riley wanted to usher Andy out as fast as he came in, but part of her wanted to learn more. All in the same she put on the tough girl card.
“Fine, “Bianca”, what do you want? And why are you here?”
“Like I said, I was wondering if these panties are yours?”
“I mean…” she trailed, shrugging in frustration. “I mean they look like they could be—I dunno man, I have a lot of underwear and I’m lazy as fuck, are they mine or not?”
Andy was a bit disappointed that Riley wasn’t joining in his little game but remained in character. “They are.”
Riley wasn’t exactly disturbed that he was wearing them or how he got them, it just felt weird to her. “Okay, did I lose them in the laundry room, and you’re being a little fucking creep trying to return them? What’s going on here?”
“I stole them, from your room” Andy explained, putting his hands behind his back and raising his toes in the heels.
Riley did a face palm. This is what she gets for never locking her door and then living a life outside of it. That would explain why her messy room seemed to be even messier upon her returning from wherever, but she went from disturbed to angry upon hearing this revelation; that this stranger stole from her.
“What the fuck?” she asked. “Why did you steal my panties?”
“Cause I’m naughty” Andy chuckled.
Riley didn’t like that answer. Hot, steamy, dominatrix Riley wasn’t in the room right now. Broke, annoyed, tax paying Riley had entered and she was in a face-punching mood and not so much a spanking, face-sitting kind of mood. She lunged and pinned Andy against the nearest wall.
“Listen to me you little fucking shit. Clearly you can tell I can kick your ass into oblivion, so I am going to give you one time to—”
“I stole a corset of yours too, and some stockings” Andy mused.
Riley raised an eyebrow. “What the fuck? My good corset? No wonder I couldn’t find the damn thing. W-What is wrong with you? And give me some answers I’m sick of your little sissy routine!”
Andy sighed and got out of Riley’s grip and danced around the apartment, leaving Riley a bit dumbfounded at his bold attitude. “Oh Riley, you’re such a tough little minx. Why spoil your anger by pounding my face in when you can get the strap-on I know you have and pound my ass in” Andy cooed, bending over a crappy couch in Riley’s living room, exposing his ass.
Riley rubbed her temples, clearly being tough wasn’t working. She needed a different approach, and maybe sexually punishing this Bianca would give her the boost she needed that week, she had been known to fuck feminized guys many a times before.
For Andy’s part he was really getting into this. Regular Andy was a total pussy and didn’t even have the courage Kadıköy Ukraynalı Escort to talk to Riley in any capacity, let alone talk and dance his way out her kicking his ass.
Riley approached Andy in a very precarious position bent over her couch. She got a good view of his ass while her panties were underneath his cheeks. She blushed a little bit, he had such feminine hips for a guy.
But as much as Riley wanted something to become of this, she knew how to win over the hearts of her men…by getting them off on HER terms, and not there’s. She stopped herself short from gripping onto Andy’s cheeks, and instead pulled him up by his wig, which he did a very good job of securing.
“Yeah, I don’t think so!”
Riley used a free hand to yank her panties down and Andy stepped out of them, obviously knowing where this was going. His plan seemed like it wasn’t going over the way he wanted it to go. Maybe Riley wasn’t as easy as he first thought?
“Where are my other things?” she demanded, pulling the wig harder. Andy did such a good job securing it, that it was actually hurting him to be woman-handled like this…but he was kind of turned on by it, once he got past the pain that is. “Where. Are. They?” Riley demanded again.
“Erm—m-my apartment” Andy wheezed, forcing himself to stay in character.
“Well then you’d better direct me. Let’s go, bitch” She sneered.
Riley led Andy to the door and the two ventured outside into the sweltering San Fernando Valley heat. “Which way?” Andy pointed to the door across the hall. Riley dragged him over and she opened up the door. She figured the set-up was similar to her own apartment and walked through the living room/foyer/kitchen and down the hallway towards the two bedrooms. She first came to Carol’s room, Andy’s roommate and current shemale mistress.
“This your room?” Riley asked, pointing to the dildo machine that destroyed Andy’s ass the previous evening.
“N-no” Andy huffed. “My mistress’s, actually.”
“Whoop-dee-fucking-do. Now where’s my fucking shit?”
“My room” Andy pointed to his room next door.
Riley dragged Andy inside and threw him onto his bed, and started to rifle through his drawers, assuming that would be where he would keep them. She tore all his clothes out, and slowly started to find what she was looking for.
Andy was down, but he wasn’t out. “You know, maybe if you stayed behind you can watch her train me today.”
“Yeah, well maybe she can train you to be a better thief—ah, this looks right” Riley had found her stockings. “Where’s my corset?”
Andy pointed to his hamper. Riley again threw out whatever wasn’t hers until she found the corset. She made a slight smile, satisfied she had the things back that she never would have noticed missing had Andy not said anything. She leapt onto the bed and straddled the sissy boy sticking a finger in his face. “So help me, if I even think you’ve stolen anything of mine again—or if you so much as set one foot in my place unannounced, you can forget the cops, I’ll just kill you. Got it!?” she demanded.
Andy liked the force in her voice, but he knew she wasn’t joking, which admittedly scared the living hell out of him. So he forced a nod and an innocent smile while Riley grinned, smacking his cheek and getting off of him. “Yes ma’am.”
“Good” She headed for his door.
“I’m sure she wants to punish me. Is that something you might be interested in?” A desperate Andy asked.
Riley stopped in the doorway. She was interested, in fact she was interested in getting out her strap-on and fucking Andy’s ass right then and there, but she still had principles and she didn’t want Andy to win, considering she had the brains to realize this was part of some weird and perverse plan of his…which it was.
“How do you know what I like, exactly?” she asked.
“I can hear you. Our walls aren’t exactly thick.”
Riley rolled her eyes. “Well, I guess I can’t blame you for hearing” She sighed, she looked at the cute innocent sissy sitting so obediently on his bed, like a long lost puppy in need of some love. But Riley believed in tough love, and more to the point, she barely knew Andy, hell she didn’t even know what he looked like without the girly clothes and makeup considering any encounter they had before went less than nowhere.
“There are a million ways you could have introduced yourself to me. But you steal from me and just assume that if you can tug at my perversions that I’ll just be putty in your hands? Fuck you” she stomped away, leaving Andy in a mess of his own sexually frustrated pomposity.
He laid back down on the bed and heard the front door open and slam shut just a few moments later. Andy felt depressed. He slumped out of bed and looked at himself in the mirror, his makeup was running from getting misty eyed from being woman-handled, but more so from his plan ultimately failing. He took up the makeup kit and reapplied some of it, knowing Kadıköy Üniversiteli Escort Carol would be very angry if he didn’t look perfect, he had already fucked one potential relationship, he wasn’t about to ruin two in a single day, that would be a new record to his already pathetic love life.
Riley stomped back to her apartment, slamming the door shut, while locking the deadbolt and the chain lock, as if to say she was never leaving her door unlocked again. She marched to her messy room and lazily dropped the contents she carried right back to their previous place before Andy had stolen them…and washed them, and folded them.
She slopped onto her bed and crossed her arms. Like many people with weird sexual desires, Riley didn’t have a group of friends she could vent to about these recent events. Other than the men she humiliated and fucked, it was her secret alone…and apparently Andy’s and anyone else in her apartment complex within earshot. Imagine a split screen now with Andy and Riley laying on their beds. Their meet-cute was more like a meet-ugly, an utter failure. All Andy could think about what a screw-up he was and that he couldn’t do the one thing he enjoyed in life correctly, a sad state of affairs in a bevy of ways.
Riley on the other hand was starting to think of the missed opportunities. She knew every way to punish a man, even ways that would only sexually benefit her, she knew just how she could have gotten revenge on Andy but she stuck to her guns. She liked to get to know her clients a little bit before fucking them (which just amounted to them saying how much they cheat on their wife or girlfriend) and in reality she was just taken off guard by Andy’s random boldness and his fast and loose petty theft of her things.
“Fuck” she turned and screamed into a nearby pillow. “Fuck! I can’t believe I just did that! God that little fuck was such a cutie! Grrrrr!” She kicked her feet, then screamed into the pillow again. “Why do I always get the weird ones!?” she moaned.
She sighed. She was a twenty-something with more problems than letting a possibly sexy romp slip through her fingers. Riley laid there for a few moments. Maybe she was being too harsh on Andy? To be fair, grabbing him by the hair was a suitable punishment instead of filing a police report, but maybe she went too far?
After all, what did he steal? Three articles of clothing she barely realized were missing until he pointed it out? And he looked so hot in drag. She wondered a little bit what Andy looked like without it on? Which then made her believe why she never noticed him before because he probably looked ordinary, cause he did.
Whether it was her urges calling her, as Riley was getting warm and moist underneath her panties; or a need to try to be a better person, Riley got up, and walked over to her equally disgusting bathroom and briefly fixed her hair.
She headed for the front door and unlocked it. She opened it up but quickly closed it when she saw someone across the hall going into Andy’s apartment. She opened it just a crack. It was a woman, several years older than her, with platinum blonde hair, hour glass frame with plump features, namely big tits, and a massive butt, Andy’s roommate/trans mistress: Carol Larzaretta. She carried with her several bags along with a tote bag. She walked inside, and closed the door behind her and Riley heard the deadbolt turn. She sighed, figuring this was definitely a missed opportunity, and closed the door in defeat. Little did Andy know, that while it looked like he had lost the battle, the war had just begun, and his odds were starting to look kind of good.
Inside Andy and Carol’s apartment, Carol tossed the bags aside and summoned her sissy. “Bianca? I’m home!” she called like Ricky to Lucy.
Andy, still dressed like a slut stumbled into the living room. “Car—Mistress, you’re home early” he blurted, breathing a sigh of relief that nothing had happened with him and Riley as Carol would have seen it and probably would have reacted negatively upon seeing it.
“Yeah, I clocked out early and thought I’d get us a few things, but look at you” she chirped. “I guessed your size but I had no idea you would fill this outfit out so well. You look like such a little sissy slut. How do you feel?”
Admittedly lousy, except for the fact Carol probably would have punished him hard if she ever found out he tried to bottom to Riley. But, a part of him wanted her to find out, maybe she would punish the two of them…or maybe Riley would turn the tables and punish him and Carol…actually, the possibilities seemed endless, but Andy figured the Riley ship was sailing fast and he had to save face for his bubbly mistress.
“I feel fantastic” Andy beamed in the fakest girliest voice his depression could muster.
“Good” Carol approached the sissy boy and rubbed his cheek. Andy was afraid he had a tell and Carol would have discovered that he went over to Riley’s without permission Kadıköy Vip Escort asking her to fuck him.
In a way he was wondering what the harm actually was? He made it sort of clear in his drunken moment with Carol that his heart belonged to Riley and that Carol’s goal was to train him to be a sissy, so what strings were attached, exactly?
Then again, he wasn’t fully aware of Carol’s terms of his new role. Was he allowed to ask strange and lazy dominatrix’s to fuck him or did he have to ask Carol’s permission first…if such a privilege would even be afforded to him?
Fortunately, Andy kept a straight face while Carol smiled, his ruse apparently working. “Come with me, Bianca. It’s time for the days training” she ushered him into her room, carrying two of her bags with her.
She sat down on her bed while Andy obediently stood at attention with his arms behind his back. Carol slapped her lap and Andy figured correctly that was his cue to get over her knee. He plopped down and leaned forward, his ass sticking up in the air, the skirt only covered it partially at this angle, but Carol flipped it up. She rubbed his hairless ass down.
“Such a cute little tushy” she licked her lips. “Have you been training yourself with your vibrator?” Carol sternly asked him.
“Yes, Mistress.”
“Good. Soon I want you to be able to take my dick in your tight little ass, but for now I think I’m gonna spank it” Carol raised her hand and without warning, came down hard on Andy’s ass. He yipped. “You’re a bad little sissy bitch, Bianca. Bad little bitches get spanked on their hot asses, understand?”
Andy nodded. “Y-Y-Y-Yes, m-mi-mi-m-mistress.”
Carol raised her hand again and slapped Andy’s cheeks, and his legs writhed from the pain. Carol made a few more slaps to his rear in slow intervals at first before picking up the pace and simply walloped his cheeks.
Andy winced as he could feel his ass reddening from Carol’s strangely strong hands coming down hard on him. He felt tears forming in his eyes. At first he thought this was from the spanking, but in reality, it was from the missed opportunity with Riley. This being his one true chance with a newly found confidence to casually ask to fuck, and it failed spectacularly.
Carol stopped a moment to grope Andy’s cheeks, spreading his pink melons apart and watched his formerly virgin asshole pucker. She let some saliva fall out of her mouth and it landed on his bullseye. She used one hand to continue to spank his cheeks one at a time while using her free hand to finger inside of him with her middle finger as if to say “fuck you, you’re mine.”
This of course was quite loud, and with their very thin walls it was attracting attention…certain attention. Riley was back in her bedroom laying on her mess of a bed. After perusing TikTok for several joyless minutes she started to hear the faint yet familiar sounds of hands coming down on skin…hard, something she was used to doing.
This was followed by the sound of high pitched feminine moans. Riley turned off her phone and was dead silent. Andy was right, their walls were paper thin. ‘Is that what they hear?’ Riley thought to herself.
She could hear Carol ordering “Bianca” to stop being such a little bitch while continuing to finger and spank his cheeks. Riley groaned, shoving a pillow on her face. In frustration she threw it off, completely disappointed of her missed opportunity to fuck this seemingly new sissy in town. If only she didn’t want to punish him by cock-blocking him, which was now ironically being more of a punishment to Riley than Andy, at least he was gonna get some dick while she just laid there, alone.
But the sounds…they were so…hot. Riley bit her lower lip as she shut her eyes thinking about the sex scene that might have been. She tore her pants off and shoved two fingers right into her clit and rubbed furiously, huffing as she listened to the scene going on next door.
In Andy and Carol’s apartment, Carol had finished with the preliminary work, sort of. She had ordered Andy on his back while she tore off her pants, straddling the boy’s face with her ass. Andy looked up and saw Carol’s now familiar dirt star a mere few inches from his face.
“Now Bianca, good sissies service their mistresses in every way that they can, and that includes when they wish to sit on your face. So you are going to lick my asshole until I am satisfied, got it?”
“Yes Mistress” Andy nodded.
Carol dropped her ass and her perfect asshole hit and right in the mouth. He started to kiss and suck her hole before sticking out his tongue and rimming her sides. Carol’s large cock was now in full view and she started to stroke it.
“Yes Bianca. Good girl, lick me just like that” Carol cooed.
Andy continued his good work, again kind of wishing it was Riley who was smothering him, but he enjoyed being able to grab Carol’s massive cheeks while she shouted commands at him. After another moment, Carol lifted herself off of Andy to get a breath.
“Catch your breath, and lick my balls” she ordered.
Andy got a few deep breaths before Carol moved her ball sack into his open mouth while Andy tongued and played with them, making Carol giggle. She continued to furiously stroke herself while Andy tongued her sack.
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