Bus Stop Blackmail (Long)

The following story contains scenes of crossdressing, public self bondage, feminization, homosexual oral sex, cum eating, and the eventual ATM. All characters are over 18. If you don't like stories with those themes, turn away now.

——————————————————

Anthony sat in his car, scouting the location. His heart raced as he worked up his courage. He hadn't seen a car for at least an hour. He straightened his dress and checked his makeup before throwing the bag of goodies over his shoulder. Cool summer air washed over his legs as he shuffled uneasily on his high heels. Anthony reflected on the events that led him to where he was. He knew if he got caught; it was all for nothing.

SIX DAYS EARLIER

Anthony leaned back in his chair. He ran his fingers through his long brown hair, and rubbed the tension from his neck. It was barely Monday and he had a lot to do that week. First thing everyday, Anthony checked his email to plan his day. One email stood out from the same interdepartmental bull shit that propagated his inbox.

'Local man caught wearing panties.'

He'd had company training on not opening strange emails but the subject line was irresistible. It was likely just a link to some no name porn site; but he might get the chance to see some hot looking transgender women doing dirty things to each other. He looked over his shoulder before he opened the email.

"Oops, how did that happen!" He played like he didn't mean to open the email.

His entire mood changed when the top of the email contained a collage of pictures, not of beautiful transgender women, but of him in various states of debauchery. Anthony panicked and turned his monitor off while flipping his head around to see if anyone might have seen the images on his screen. Luckily he had the last cubicle down the hall near the restrooms. No one ever walked past his cubicle unless they were specifically looking for him.

"What the fuck!" He hissed under his breath.

He stood up and looked around to make sure no one was coming toward his end of the office. Nothing looked abnormal so he sunk back down into his chair. Anthony cautiously turned his monitor back on and the images of him in lingerie slowly faded back into view. Inside, he found pictures of himself dressed in lingerie and in self-bondage from less than a month earlier along with a specific set of instructions.

"Dirty Bondage Slut,

You've been caught, if you don't comply with the requirements, these pictures will be posted on all of your social media accounts, it will be sent to your employer, and your wife. You have one week to upload a video showing the completion of all tasks or there will be repercussions.

These are your tasks.

1. Shave everything from your eyebrows down, and pluck your thick eyebrows into a thin feminine arch, wear a minimum of eyeliner, eyeshadow, and lipstick.

2. Wear panties, a stuffed bra, a corset, and stockings, write cum slut on your chest, and sissy clit over your dick.

3. Take a large dildo to a bus stop bench. Wearing a dog collar, and your hands cuffed, set up a camera, and ride a large dildo for five minutes.

4. Suck it clean for at least a minute before cumming in your mouth.

5. Lock your hands back up and return to your vehicle before swallowing your load.

Just reading the instructions made Anthony's cock head twitch, but he was also filled with terror thinking about what might happen if he didn't complete all the tasks. He couldn't imagine who else might know about his extracurricular activities, and couldn't imagine anyone simply stumbling upon him during a play session. He had always been careful in choosing his locations for their privacy.

Anthony tried to picturea scenario where he could pull the scene off without anyone finding out but no situation seemed to work out. His wife would surely notice the shaving and plucking of his eyebrows. He could hide everything else, but he was going to have to find some excuse to shave.

Anthony re-scanned the email looking at the photos. The most damaging photo showed not only his face quite clearly, but he was kneeling with his hands cuffed behind his back, sucking on a large dildo. He wore a face full of slutty makeup, a bra, panties, and thigh high stockings. If anyone saw that photo alone, he would most likely be ruined for life. What's more is, they had video too.

Anthony peered over his cubicle wall and looked around to see if there was anything suspicious, or someone gawking at him but nothing stood out. He hit play on the video and watched himself from behind for the next three minutes. Anthony always thought he looked good in lingerie but from behind her thought he could have been watching a video of a tall thin woman sucking on something. He could see his little pecker tenting his panties as his body rocked forward and back.

The cameraman quietly changed positions and recorded the scene from the side. His long dark brown hair partially obscured his face as he continued face fucking the dong. Anthony rubbed his dick through his slacks while watching himself on the computer. He wished he could wear panties all the time but his wife Hailey seemed somewhat resistant to the idea. He knew she would lose her shit over the email for sure.

Anthony forwarded the message to his personal email account and deleted the original in case the women in the HR department caught wind of the email. He didn't need to be outed before he even got the chance to comply.

Anthony sat in the break room sipping his coffee, watching his coworkers hurry in and out, wondering if any of them could have sent the email but no one acted any different. He pictured what he had to do. Anthony had everything he needed except the location and a couple of miscellaneous items. He had a couple of ideas for a location but needed to narrow them down more. With only a week to complete his tasks, he needed to get started right away.

"Hey Dude, it's almost lunch!" Kevin said slapping Anthony in the back.

Kevin was Anthony's oldest friend, they met at the same time Anthony met his wife. Kevin either only dated the hottest women or the odd assortment of good looking guys. There was always a rumor floating around that the women weren't actually women, but for all appearances, they were good-looking girls!

"Yeah, about that!" Anthony faltered.

Anthony couldn't help but look at his friend. Kevin was two inches taller; standing right about six foot two and well built. His dark red hair normally cascaded down his shoulders but was wrapped up in a man bun for work, and his business attire hid a chiseled body that many of the women in the office swooned over. Anthony was the complete opposite. No one ogled over him, except Hailey. Anthony had no idea how he landed a looker as hot as she was!

"Bull shit, you're not ditching me again dude!" Kevin said pulling Anthony to his feet.

Anthony liked it when Kevin touched him. He'd had a crush on him in college but left his homosexual feelings behind when he met Hailey, well... for the most part. He often wondered what life would look like had he gone the other way though.

"Don't you have work to do? I never see you actually working!" Anthony asked following Kevin to the elevators.

"It always gets done by someone or another!" Kevin laughed.

Kevin led Anthony into an Italian restaurant just around the block and they sipped their drinks waiting for the food; shooting the shit when a gorgeous looking woman huffed in and speed walked straight to their table.

"Oh, you're with him again?" She grumbled with her hands on her hips, flipping her hair out of her face.

"Calm down Nessa, that's Anthony, he's my friend!" Kevin said like he was talking to a two-year-old.

Anthony just sat back and enjoyed the show. For all its drawbacks, being married had certain benefits that were becoming more and more apparent as the woman yelled at Kevin in the middle of the busy restaurant.

Anthony couldn't help but check her out as she yelled. Her ass jiggled as she shook her finger at Kevin, and her large breasts heaved up and down as shesobbed between shooting fits. She was wearing high heels with what looked like a 2" heel and was every bit as tall as Anthony. Nessa stormed off and everyone snickered as she passed.

"This isn't over Kevin!" She sobbed. Her hips popping side to side as she scurried away.

"Who was that? She was kinda cute!" Anthony asked jabbing Kevin in the side.

"I just dumped her last night, she got too possessive for me."

"Every woman I see you with is fucking drop-dead gorgeous! Where the hell do you find these women?"

"Strip clubs!"

"I've never seen a woman like that at any strip club!"

"You're going to the wrong strip clubs dude!"

Their food arrived shortly after Nessa made her angry exit from the restaurant and they dug in aware that the restaurant might have not been the best choice for a quick lunch. Anthony still had so much to get done before he could go home for the night and he rushed back after lunch to get to work.

He couldn't shake the heavy feeling in his gut over the email and he opened it several more times to read it and scour the pictures for clues to who it could be from. The email address was just a bunch of random letters and numbers that didn't make sense. The angles of the pictures were either behind him or from about thirty feet in front with minimal real vantage points. Whoever it was, got only feet away and he didn't notice them at all!

As the day closed out Anthony drove home with his mind on the email and how he'd gotten caught. Hailey had been home for a couple of hours and had dinner ready when he stepped through the door.

"Hey darling, oh nice, dinner is ready!" Anthony said hanging his keys on the hook by the door.

"Yeah, I got home and just wanted to do something nice for you. I didn't have time to do anything this morning." She said running her fingers through her long red hair.

Anthony licked his lips and drank in the vision of his wife. He slid in close behind her to place his hands on her trim waist. She pushed her juicy ass out and rubbed it against his crotch. Anthony was instantly hard and cupped her breasts while he kissed below her ear.

"Yeah, what do you have in mind?" Anthony asked nibbling on her earlobe.

"I can think of a couple of things!" She said setting two plates of food on the table.

Hailey gently rubbed Anthony's leg while she ate. He became increasingly aroused with each inch she got closer to his crotch, and soon he found it difficult to concentrate on anything but her hand. Anthony forced several mouthfuls down and retreated for the bedroom, kicking off his shoes and pants along the way.

He was almost completely naked when Hailey gently pushed him face-first onto the bed and climbed on top of him. He could feel her nakedness on his legs as she started rubbing his back. Everything melted away in her hands as she rubbed and worked unknown sore spots. Hailey massaged from his shoulders to his toes and then made him flip over onto his back.

He knew he was feeling good but didn't expect his cock to be standing straight in the air having ejaculated earlier that morning. Hailey stroked him for a moment before starting on the tops of his legs and working up around his stiffness to his chest. He was just about to doze off when he felt the warmth and wetness from Hailey's mouth cover his dick.

"Oh god... that feels so good!"

Anthony looked down to see his wife's lips resting on his pubic bone. His cock was buried in her throat and she didn't even gagging. He could feel her tongue searching around beyond her lips, as though she were looking for his balls. Hailey bounced her head up and down for a moment before she straddled his face and lowered her wet slit onto his mouth.

Her womanly scent filled Anthony's nostrils and he opened his mouth to suck on her clit. His tongue flicked at her bean and she pressed herself onto him. Hailey moaned around Anthony's cock and ground herself into his face. Anthony's nose entered her hole and he struggled to breathe while she smothered him.

He pulled his face away stealing a breath as Hailey worked the tip of his dick with just her lips. She pushed her hips forward rubbing her clit on his chin; her asshole rested right on his nose. He always wanted to fuck Hailey in the ass but she would just say 'There's a perfectly good hole right next-door!'

Anthony spread Hailey's butt cheeks apart and craned his neck to stick his tongue right into her asshole. She slumped onto him and moaned loudly as Anthony tried to lick her insides. He felt so whorishly dirty licking inside his wife's asshole but in such an exciting way.

"Awe fuck, mmmm. Fuck!" She grunted as he tongue fucked her tight hole.

Hailey abandoned Anthony's cock and pushed her ass onto Anthony's face. She looked back over her shoulder and smiled as she saw her husband eating her ass.

"I need you inside me right fucking now!" She moaned pulling herself away from Anthony's face.

Hailey scooted down, still facing away from Anthony, and rubbed her pussy on his stiff erection. He guided his cock head into her wet hole and she pushed herself back onto him. Her heavenly pussy washed him in pleasure as velvet-like friction pulsed in his loins.

"Finger my ass baby, I need you in both holes!"

Anthony spit on his thumb and pressed the tip into her hungry shit hole. She was still slick from his tongue so his thumb slid in partway before he felt her tense up against him. He stopped pushing but didn't ease the pressure until she loosened enough for his thumb to slide all the way in her ass. She continued riding his cock as she pulled her ass cheeks apart to open herself up for him.

Anthony could feel his cock ramming her twat with his thumb and her pussy started to spasm on his cock. Anthony's head swam and Hailey gripped his legs tightly.

"Oh god, fuck Anthony, fuck, fuck!"

Anthony went rigid and the familiar sensation flowed from his balls into Hailey's pussy. He shot deep into her womb and her twat became twice as wet. Hailey reached back and pumped Anthony's thumb into her ass as she ground herself onto him.

"Jesus Christ! Who the hell are you and what did you do with my wife?" Anthony breathed.

"That was really nice, thank you, baby!" Hailey exhaled, uncoupling herself from Anthony's cock.

Anthony could see his cum already dripping out of Hailey's pussy. He reached out and ran his fingers through their combined juices. Without catching Hailey's attention, he licked his finger clean savoring the mix of musty womanhood and metallic semen.

"Come shower with me?" Hailey exhaled, Rubbing a towel between her legs.

Anthony thought about the email as Hailey washed his back for him, the taste of his semen and her juice still lingered on his tongue. He'd have to shave his whole body and pluck his eyebrows. How was he going to explain that to Hailey? She rubbed the soap down his back and across his asshole. He instinctively pushed himself back to meet her hand. She didn't pick up on his questionable behavior and continued lovingly washing his back.

Anthony returned the favor and washed Haileys back for her. He tried to slip a finger in her ass but she wasn't having any of it and yelled at him for even trying. Anthony got out of the shower leaving Hailey to savor the hot water alone a minute longer. Anthony dried off and crawled into bed naked.

He opened his laptop and re-read the email for the hundredth time that day. Still, nothing stood out as a clue. Hailey was done with her shower and climbed into bed next to him. He shut up his laptop and tried his best to get some sleep. Visions of naughty sex filled his dreams that night and he woke up feeling extra horny.

Anthony snuggled up to his wife and pressed his erection onto her ass.

"God, I just gave your sex last night! I'm trying to sleep!" She rejected him.

Anthony groaned and pressed his stiffness into his wife's ass again before rolling out of bed. He just wanted sex again but she only ever wanted sleep. Anthony drug his feet to the bathroom with his cock bouncing around in front of him as though it were suspended from a magical string.

He gently stroked his dick until he got to the bathroom and locked the door behind him. Anthony scanned the floor for a prize. Most mornings that he got rejected; he would take care of himself with a pair of his wife's panties. That day was a special find. The yellow bra and panties lay in a pile under Hailey's clothes. The nylon string bikini panties were encrusted with womanly juices that hardened the gusset into the most aromatic piece of fabric he knew of.

Anthony pressed the crotch of the panties into his nose and sniffed hard, he loved the smell of his wife's pussy. The next best thing to the real thing was her dirty panties. He first pumped his cock while he sniffed her panties, and visions of self bondage filled his thoughts. He imagined getting caught by a couple sexy police men at the bus stop.

He would already be cuffed when they caught him. He'd be wearing his sexiest lingerie. One would force his cock down Anthony's throat while the other ripped his panties down and raped his ass. It wouldn't really be rape though, Anthony would be a willing participant... well, as far as the fantasy went. He couldn't see himself actually cheating on Hailey, but he could imagine whatever he wanted.

Anthony stepped into his wife's sexy yellow panties and left his cock poking out the top. He was close to cumming already with her only a few feet away as he used her lingerie as a masturbation aid. Anthony laid on his back with his legs against the wall and positioned his cock over his face. He wanted to cum right in his mouth more than anywhere else.

It didn't take long before he felt the tingling sensation between his balls and asshole as his orgasm neared. Anthony opened his mouth and imagined the cop standing over him jacking off. He wanted his creamy reward. Anthony's balls tightened and the first glob took him by surprise when it landed on his chin. He tried to adjust his aim but the next spurt landed right in his eye.

Anthony clapped his eyes shut and stuck his tongue out searching the air for cum. The next two spurts landed right in his mouth. He didn't register the taste immediately, but as the globs dripped to the back of his throat, he sensed his flavor. The cum was sweet and fruity with a hint of metal and dish soap. As Anthony closed his mouth to swallow, another glob landed on his pursed lips and licked them clean.

He played with the cum on the tip of his tongue as his orgasm faded away and his legs toppled his body sideways. He licked his lips again to get the last taste of himself before turning the water on to shower and get ready for work.

The water felt good against his skin and he soaked for a moment before washing the cum from his face. He wondered who the mystery email might have been from. Whoever it was, they were quite sneaky, as he didn't hear or see anyone that night. When he needed self bondage time, he usually got a hotel, but the night in question, he decided to play in an abandoned parking garage. Hotels had lost their excitement and a parking garage was the next best choice for an exhibitionist. Maybe not that parking garage, or that night in hindsight though.

He'd picked the location for its privacy and found the cameras were disconnected. He couldn't think of any that might have still been operational with an angle that matched the pictures or video. Whoever it was had been there in person.

Anthony left for work, kissing his wife goodbye for the day. He insisted on the usual kiss and grope before leaving. Hailey squeezed his ass and patted him on the back during their hug sending him off to work before she left like normal. Hailey worked as an accountant at a large firm and could set her own schedule.