Bus Stop Blackmail (Long)

"You mean, I should go do myself on camera at a bus stop wearing lingerie?" Anthony asked.

"Yeah, but you should make sure you look good, and that you're wearing matching lingerie for sure!" Hailey suggested.

"All this talk about lingerie and stuff is making me kinda horny baby!" Anthony whispered.

"Yeah, What do you want me to do to you?" Hailey asked while rubbing Anthony through his thong panties.

"Mmm... I can think of a few things." Anthony said pushing his hips to meet Hailey's hand.

"Gimme a second!" Hailey said jumping out of bed and running to the closet.

She returned to bed holding a good-sized black dildo with big fake balls. She threw the covers off Anthony and held the fake dick over her crotch.

"Do you want to come suck my dick!" Hailey said stroking the dong.

"Um... okay..." Anthony said rolling on his belly between Hailey's legs.

"Now, grab ahold of my cock with one hand, and with the other, cup my balls," Hailey instructed.

Anthony grabbed Hailey's fake black cock and held her balls with his free hand. He looked into her eyes waiting for more instructions. With the hand holding her balls, he let his fingers wander a little and he made tender contact with her pussy.

"Perfect, now maintain eye contact and take just the head of my cock into your mouth," Hailey instructed.

Anthony followed Hailey's instructions and sucked on just the tip of the plastic cock. His fingers delve deeper into Hailey's pussy folds and she moaned quietly. Anthony bobbed his head up and down the tip of Hailey's cock. He was trying his best to pretend it was real. The thought of sticking his wife's cock made him even more aroused than before.

"Mmm... that feels good Annie, now take me into your throat honey!"

Anthony tried his best to deep throat Hailey's dong. He simultaneously drove two fingers into Hailey's gushing hole.

"Agh... you're such a good cock sucker! Fuck that feels great!" Hailey growled.

Anthony could feel Hailey's twat squeezed around his two fingers as her eyes rolled back in her head. Anthony felt great pride in sucking cock so well, he could even make his wife cum with a fake cock!

"Jesus Christ Annie, agh fuck... I'm cumming!" Hailey yelled.

Anthony left Hailey's big black dildo in his mouth as his orgasm settled down. He could feel a small wet patch in the front of his panties where he was leaking precum. He didn't have an orgasm, but he gave Hailey one and that's all that mattered.

"Did I do good baby?" Anthony grinned.

"Yeah, that was nice, now it's your turn! Roll over onto your stomach Annie!" Hailey said.

Anthony shot a slightly confused look at Hailey before obeying her demands. She rolled off the bed with the large dildo in hand and stood behind him.

"Drop your panties, Annie, I want to make you feel good!" Hailey said.

Anthony pulled his panties down over his ass and pushed them down to his knees. He felt Hailey's hands touching his ass cheeks and spreading them open.

"Hold your cheeks open honey!" Hailey said.

Anthony pulled his ass cheeks open, expecting a hard dong to press against his hole but she licked his hole instead. Her hot breath warmed his balls and his hole loosened as she licked from his premium to his tail bone. Anthony had never had his asshole eaten before, and he was in Heaven. He could feel Hailey's long tongue driving its way into his bowels and he started wanting her big dick inside him.

"Oh fuck, that's nice!" Anthony shouted.

His dick was hard as steel and poking at his belly but he couldn't care less. He just wanted her in him!

"Please Hailey, fuck my ass! I need to feel you inside me so bad right now!" Anthony pleaded.

Hailey licked and sucked at Anthony's asshole. She waited until he was nearly shaking with desire before moving her tongue away from his hole.

"Where do you want me to fuck you, Annie? Hailey asked.

"Put it in my ass please, fuck my ass Hailey please!" Anthony pleaded.

"That's not your ass when something is going in it, do you understand?" Hailey said as she placed the head of the black dong at the center of his dirty little fuck hole.

"That's your ass pussy Annie, do you understand me, honey?" Hailey asked.

"Please fuck me in my ass pussy, Hailey, I need you so bad right now! Anthony begged.

Hailey started pushing the dong into Anthony's ass pussy. Anthony pulled his ass cheeks as wide as he could and started pushing back into her cock. He needed her inside him all the way. He needed to get fucked hard. Anthony arched his back and looked over his shoulder at his wife giving it to him. She was beyond beautiful at that moment as he felt her start to pull the cock out slowly.

"God, fuck me, Hailey, just fuck me!" Anthony encouraged.

Hailey tried using her hips to fuck her husband but she couldn't figure out the rhythm and abandoned using her hips. She crouched down and jabbed at his fuck hole while holding his cock. Anthony wailed into the air and bucked his hips, trying to meet her movements. He needed to cum more than anything and started mumbling nonsense.

"Mmm... agh... god damn, mnnmhgh!" He grunted driving his fingers into his mouth and sucking them like a cock.

Anthony wished there was a cock in his mouth at the same time, he wanted to be filled from both ends! He needed more cocks.

"God I want to suck a dick so bad right now!" Anthony yelled.

"Grab your sissy clit you dirty cum whore!" Hailey demanded still fucking his ass pussy.

Anthony gripped his cock so hard the head turned an angry shade of red.

"Go ahead, cum whore, take my cum in your ass pussy, jerk that sissy clit of yours Annie! Hailey yelled.

Anthony stroked his dick furiously as he could. Hailey's hand waited at the tip to catch his seed and he started filling her hand. Anthony's legs shook and his ass quivered.

Aaaaggh... fuuuuuuuck! Mmmmmmm!" Anthony grunted as he came harder than he ever remembered.

Hailey pulled the dong out of his ass and air rushed in. His hole stayed open for a few moments as it seemed to be searching for the cock that belonged there. Hailey coated the black plastic dick in Anthony's cum, held it up to her crotch, and stuck it near his face.

"Clean my cock off cum slut!" Hailey demanded.

Anthony wasn't sure if she was serious until she slapped him on the cheek, spreading cum all over his face. She brushed it across his lips, and as he opened his mouth to take the cock, she turned her hand over and dumped his seed into his open mouth.

Once he cleaned her hand good enough, she pushed the dirty dong into his mouth.

"Clean my dirty cock you filthy cum slut!" Hailey laughed.

Anthony gritted his stomach and pushed through a mixture of tastes. The most noticeable was his cum. He knew that pretty well. Its smooth metallic flavor was easy to find, but there was an unfamiliar sweetness, and the faint odor of shit mingling together. He was sucking on something that had just been pulled from his ass.

Anthony gagged, not because Hailey pushed the dong to the back of his throat but more from the thought of having shit in his mouth. It didn't taste bad, it was just the idea.

"You're such a dirty whore sucking your ass off that dick!" Hailey said, calming down.

She pulled the dong free with an audible pop. She was satisfied he cleaned it good enough as she set it on the side table and collapsed into the bed next to Anthony.

"That was so nice Annie, you're such a good lover!" Hailey whispered petting Anthony's hair.

"I can't believe you made me suck on that after it was in my ass!" Anthony whispered back too exhausted to move.

"Well, you're going to have to do the same thing when you go to the bus stop, silly girl... Hailey said. "Was it as bad as you were acting like it was?

"It was kinda gross. It was mostly the thought though." Anthony admitted.

"How did you feel when I shoved it into your mouth?" Hailey asked.

"I felt so dirty, it was so degrading, but once I got over gagging from the thought... it was kinda hot too!" He said smiling shyly.

"You should go brush your teeth, Annie!" Hailey suggested. "Then we can go to sleep!"

Anthony brushed his teeth and got back into bed. Hailey snuggled with him until he fell asleep add the next thing he knew was Hailey was walking him up to get ready for work.

"Wake up sleepy girl, come on! You're going to be late." Hailey whispered.

Anthony jumped up and headed for the shower not realizing Hailey had woke him up an hour early until he had started the water.

"Hey, what time is it?" Anthony hollered noticing how dark the sky still was.

"It's five o'clock babe!" Hailey said stepping into the bathroom completely naked and holding a towel.

"Why did you wake me up so early!" Anthony grumbled.

"You need to shave, and find an outfit Annie, that takes more time than just throwing in whatever doesn't stink honey!" Hailey said pushing Anthony into the shower.

Anthony stepped backward into the hot water and screamed. "Agh... that's fucking hot!"

"Oh, don't be such a girl!" Hailey chided, and laughed once she realized the irony.

"Take this razor and start with your arms," Hailey said pushing Anthony out of the hot water.

"What? Why am I shaving my arms?" Anthony asked.

"Once you're done with your arms, shave that little tuft of hair off your chest too honey, then I'll help you with your back and armpits okay?" Hailey said soaping up her perfect breasts.

She gave Anthony the puppy dog eyes she used whenever she wanted him to do something he didn't want to do.

"Fine, whatever, but why do we have to shave my armpits?" He cried.

"Look, the email said to shave everything below your head! You're going to be wearing panties but you'll be fucking yourself at some point so you might need to shave your ass too, and your legs!" Hailey said looking sternly at him like he should know already.

"Yeah, I forgot about that." Anthony realized.

Anthony shaved his whole body with Hailey's help. They left his anus alone and they left a small landing strip right over his dick.

"It looks so feminine shaved like that!" Anthony said looking at his crotch.

"Yeah, that's kinda the point Annie!"

Hailey tossed Anthony a pair of cream thong panties and the off white longline bra. He just gave her a puzzled look.

"They match close enough Annie, besides... who are you going to be showing your panties to at work anyway?" Hailey asked.

"I just didn't think I'd be wearing a bra to work it's all!" Anthony said holding the lingerie.

"Would you rather wear the maximized bra with the inserts?" Hailey asked pulling the light pink bra out of the shopping bag.

"No, no... this one is fine!" Anthony said pulling the bra over his head and down over his chest then stepping into the panties.

He got dressed the rest of the way without Hailey's help, but stepped into the bathroom to check for panty lines and popped bra straps out funny bumps that might be noticeable through his shirt. He could just make out the bumps from his bra but hoped no one would notice.

Anthony noticed Hailey's makeup laying on the counter and thought back to their conversation about how she bet money that she could get him in women's clothes and makeup. He picked up a small tube with small paneling that read eyeliner.

Anthony had heard stories about men that got away with wearing eyeliner and he wondered if he dared try it. The men he heard of were either ultra-feminine or ultra-masculine. He wasn't sure where he fell on that spectrum. He was sure Hailey would place him on the ultra-feminine end of the spectrum and then insist that he start wearing makeup everyday.

He just stared at his face and imagined a little eye makeup on. Eyeliner, eyeshadow, and mascara. He imagined looking like Chris Angel, doing street magic with his fingernails painted a dark red. Everyone accepted Chris Angel because he was a magician. Anthony wasn't a magician though.

"Hey, whatcha got there?" Hailey asked barging into the bathroom.

"Nothing!" Anthony said palming the eyeliner like Chris Angel.

"Lemme see Annie!" Hailey insisted.

Hailey pried the eyeliner tube from Anthony's hand.

"Were you thinking about putting on some makeup today?" Hailey giggled.

"No, I was just thinking." Anthony stammered.

"Come on, let me do your eyes babe!" Hailey begged.

"No, not right now Hailey' I've got to get to work." Anthony insisted.

"Please Honey, I promise it'll look good I swear!" Hailey tried again.

"No, not right now!" Anthony said.

"Can we do it tonight after work?" Hailey asked.

"Sure, whatever." Anthony offered.

"Okay, Promise me you won't give me any shit and you'll agree to whatever I want to do!" Hailey begged.

"Okay, I've got to go to work now!" Anthony said trying to walk out the door.

"Say it, Annie, Promise me you'll do whatever I say!" Hailey demanded.

"Okay, I promise, I'll do whatever you want and I won't give you any shit!" Anthony said closing the door and leaving for work.

He already felt weird enough wearing thong panties and a longline bra under his work clothes, he didn't need to show up on a Thursday wearing lingerie and makeup. That was probably a Monday sort of thing and probably only after having experimented with various other feminizing actions.

He may have played around occasionally before, but in one day he started wearing panties and bras. Anthony felt as if the pace kept up, Hailey would have him going through sex-change procedures by Friday! All the feminizing clothes and such were exciting as hell but he couldn't ever see himself wanting a sex change! He thought he would enjoy everything more with a penis than a man-made vagina!

(insert break room encounter with the young blonde receptionist Jen who notices Anthony looks different, he looks happy for the first time since Jen met him. He admits to wearing fancy new underwear quietly and she places her hand on his shoulder in a mock show of shock and notices his bra straps. The full realization of what his fancy new underwear sets in and she tells him to relax and that his secret is safe with her. She is an ally and will be there to support him whenever he needs it.)

Work isn't bad for the first half of the day, Anthony expected Kevin to stop by to check his underwear but he didn't even make an appearance until lunchtime anyway.

"Hey sissy whore," Kevin said far louder than Anthony was comfortable with. "Where are we going for lunch today? I kinda want a repeat of yesterday! Street tacos in the park!" Kevin said almost laughing.

Anthony just glared his disapproval. He sucks his friends' dick one time and he turns into a pig!

Kevin leaned in close and grabbed Anthony by the shoulder and in surprise, he felt around Anthony's back.

"Are you wearing a bra, Anthony?" Kevin exclaimed.

"Not so loud Kevin!" Anthony growled.

"I want to see it, I want to see it all Anthony!" Kevin demanded.

"I'm not taking lunch, I have too much to do today!" Anthony lied.

"You can just show me in the bathroom right now!" Kevin insisted.

"No, not here at work! What if someone walks in on us?" Anthony cried.

"Come on, get up! No one is here anyway, and if you prolong this, people are going to start coming back... it's going to happen, Anthony!" Kevin insisted.

"Fine, I'll show you and then you leave me alone about it okay?" Anthony relented.

"Yeah, sure... now come on sissy whore!" Kevin said gesturing toward the men's room.

"And stop calling me that Kevin!" Anthony said walking toward the men's room.

Kevin raced past Anthony and opened the large handicap stall. "Ma lady!" He said with a big animated gesture.

"You're such a dork Kevin!" Anthony said stepping in.

Kevin turned around and locked the door, then stepped down to check that the other stalls were empty. Satisfied, he returned his attention to his friend that was unbuttoning his shirt. Once Anthony was standing in only his bra, Kevin pointed at his pants excitedly.

"Those too Anthony, I want to see it all!" Kevin insisted.

Anthony rolled his eyes into the back of his head in disbelief. He was irritated that Kevin wanted him practically naked but what could he do? He may as well just take his pants off too!

Wearing only a bra and thong panties, Kevin twirled his finger in a circle, telling anything to spin around and Anthony complied. He was doing whatever Kevin wanted to get it over with as soon as possible.

"Oh my god Anthony, did you shave?" Kevin exclaimed.

Kevin grabbed Anthony's arms and forced them over his head. He ran his hands down Anthony's smooth armpit as though his eyes lied to him and the hair had just become invisible. Kevin started pulling Anthony's panties down but Anthony slapped his hands away and backed into the corner.

"Stop Kevin, you've seen enough!" Anthony cried, grabbing the waistband of his thong panties.

"You look like such a girl trying to hide your body from your boyfriend!" Kevin teased.

"You're not my boyfriend Kevin!" Anthony protested.

"Yeah... you sucked my dick yesterday Anthony, I'd say that makes me your boyfriend!" Kevin laughed.

"I'm married Kevin, I can't have a boyfriend!" Anthony cried.

"Call Hailey... she'll tell you that you can be my girlfriend!" Kevin smiled.

Anthony's jaw dropped and he just stared at his friend. He couldn't believe his nerve.

"Bull shit!" Anthony growled.

Kevin pulled his phone out and tapped the screen a few times and it started to quietly ring in his hand. Kevin planned the phone on his ear and waited for Hailey to answer. Anthony could only hear Kevin's side of the conversation as he stood there in disbelief.

"Hey bitch, how's your day going?" Kevin asked.

"Oh, mines been good so far."

"So, Anthony's wearing bras and panties now huh, that's exciting!"

"Yeah, that's what I thought."

"So Yeah... since Anthony is wearing bras and panties now, I told him he could be my girlfriend!"

Kevin looked right into Anthony's eyes, then his eyes wandered down Anthony's body and rested on his little package contained by the panties. Kevin licked his lips and smiled up at Anthony again.

"Yeah but then, he was all like but I am a married man I can't be your girlfriend!" Kevin said in a mock tone like he was imitating someone else.

"Oh yeah, for sure! Here he is!" Kevin said before holding the phone out in front of Anthony.

Anthony took the phone and held it up to his ear. "Um hello?"

"Hey Annie, how's your day going?" Haley asked.

"Um, good I guess," Anthony said scratching his head.

"So Kevin huh, he's pretty cute isn't he

"Yeah I guess

"Don't try and deny it, you already told me you had a crush on him. It's OK Annie.

"Yeah you're right

"Do you want to be his girlfriend

"No, I'm married to you, you're my wife

"Look last night when I was pretending I had a penis and you were sucking on it you look so beautiful, but it looked like the dildo wasn't completely doing it for you. Then when I got behind you I started fucking you, I could tell I wasn't moving it... I wasn't fucking you the way you needed to be fucked!

"Yeah, and what, you want me to become his girlfriend"

"I can't give you what you need in that department. Do you like Kevin, and he really likes you. So yeah you can be Kevin's girlfriend, as a matter of fact, I want you to be Kevin's girlfriend."

"Are you telling me you don't want to be with me anymore?

"No Annie I love you with all my heart you're my best friend I want to spend the rest of my life with you and grow old together I just know there are some things I can't give you

"I'm just worried this is going to change things with us and I don't want to lose you

"Honey, I love you, when I told Kevin that I caught you wearing my panties, he's the one that helped me understand what you needed. He's the one that stopped me from leaving you. Kevin's are a great guy, and I'm happy you found a boyfriend as good as him already.