Bus Stop Blackmail (Long)

"You got a point," Kevin said.

Anthony took a couple of bites of his taco and dropped the plate back onto the table unable to eat. He was shaking his leg causing the whole table to bounce and Kevin placed a hand on Anthony's thigh stopping him from bouncing his leg. Warm waves of pleasure shot up Anthony's thigh, right into his groin and his dick twitched enough for Kevin to notice. Anthony gasped and sucked air in sharply.

"I can't stop thinking about you in women's lingerie. You looked so fucking sexy with your mouth around that dildo dude!" Kevin said looking at Anthony sideways.

Kevin's hand crept toward Anthony's crotch and Anthony did nothing to stop his friend from proceeding.

"I haven't had sex in so fucking long!" Kevin said, still creeping his hand further up Anthony's leg.

"Mmmph," Anthony grunted.

"How would you like to suck a real dick, Anthony?" Kevin whispered into Anthony's ear.

All he could do was moan and open his legs giving his friend better access to his throbbing cock. Anthony was beyond horny from being denied that morning and not finishing himself off. He couldn't deny his arousal.

"Have you ever sucked a real man's cock, cum slut?" Kevin's growled.

"Mmmhh... no, never!" Anthony whispered.

"Do you want to suck a cock, cum whore?" Kevin growled.

"Mmm...I don't want to cheat on Hailey!" Anthony whispered.

Kevin rubbed Anthony's dick through his suit pants. Anthony throbbed in his friend's hand and neared ejaculation. He wanted to cum so bad but he wanted to taste his friend more. He needed to finally find out what it was like to have another man's dick in his mouth, more so it would be Kevin's dick! Anthony looked around the park for somewhere more private. There was a bathroom across the park and he nodded his head toward it.

"Meet me over there!" Anthony said standing up and walking off toward the public restroom.

Kevin was right behind him watching his ass the whole way.

"Swing those hips more slut!" Kevin demanded.

Anthony switched his walk and placed each foot directly in front of the other while popping his hip out side to side as femininely as he could.

"That's it whore!" Kevin said slapping Anthony's ass as they entered the bathroom.

"Just get on your knees, right there for the whole world to see," Kevin said as he pulled his large cock out.

Anthony grabbed Kevins dick and stroked it like he would do his own. He had never even touched another man's junk before that moment and excitement surged through him making his head swim.

"It's soooo big; I can't believe I'm really doing this!" Anthony said looking up at his friend.

"It's not going to suck itself!" Kevin said, pushing his hips forward.

Anthony opened his mouth and allowed the head of Kevin's cock inside. He tongued the underside of the head, marveling at its softness while being fully hard. His friend tasted good, so natural, like velvet sugar on his tongue.

Kevin pulled Anthony's head further along his cock, forcing himself deeper inside Anthony's mouth, more and more until it stopped at the back of Anthony's throat when he gagged. Anthony, being the god little slut, forced the cock deeper, inside; his throat constricted around the cock head. Kevin's head rolled back and he moaned, gripping Anthony's hair.

"Fuuuck, that's so nice! Keep it up slut!" Kevin growled.

Anthony started bobbing his head on the dick just like he'd seen in every porn movie of his life. He used one hand to Jack his friend off while the other toyed with the balls and anal opening. The cock throbbed when he touched Kevin's asshole. Anthony pushed his middle finger into Kevin's shit hole and searched for his friend's prostate. All he could think about was how much he wanted to taste Kevin's cum. He wanted to eat his load for lunch!

Anthony massaged Kevin's prostate. He could feel it swell up around his finger and he knew Kevin was about to shoot cum all down his throat. Anthony pulled back and sucked hard on the tip of Kevin's cock. The first shot filled Anthony's mouth with a salty liquid that stirred Anthony's loins. He could feel slight wetness inside his pants. Then three more shots burst in quick succession, causing little spurts to escape his mouth and dribble down his chin.

Anthony swallowed his friend's load and slurped the cum up from his chin. His tongue licked his lips searching for more cum as Kevin forced his deflating cock back into his pants. Anthony was still on his knees licking cum from his fingers.

"Are you sure you've never done that before!" Kevin exhaled.

"That was nice, but yeah... first time ever!" Anthony said, still on his knees.

"I can give you a daily supply of that if you want slut!" Kevin said adjusting his toe in the mirror.

"Mmm... that sounds nice!" Anthony cooed.

"I want to see you in lingerie... tomorrow. You'll come to work wearing panties just for me. Do you hear me?" Kevin said.

Anthony squeezed his thighs together against his cock and felt it squish around his wetness. He had cum in his boxers while sucking Kevin's cock and couldn't think of anything sexier than to wear panties for his friend.

"Okay, I'll do it," Anthony said.

"Just call me whenever you need cock from now on slut." Kevin asked.

"Mmm... I kinda like it when you call me that," Anthony replied.

"And I'll get Hailey out of the house on Saturday so you can go do your thing at the bus stop," Kevin said turning to leave.

"Oh my god, thank you so much! You're a lifesaver, Kevin!" Anthony said as his friend walked away.

By the time Anthony walked out of the public restroom, Kevin was nowhere to be seen. Anthony meandered his way back to work licking his lips and thinking about Kevin's wonderful cock and the request to wear panties the next day. Before he knew it, he was sitting at his desk absentmindedly rubbing his dick through his slacks.

The remainder of the day breezed by and he was on autopilot until he pulled into his driveway at home. He'd been thinking about his relationship with Kevin, and his wife of ten years. He wondered how everything would pan out with the three of them.

Anthony took a quick shower to refresh his mind and clean the dried spunk from his crotch. He stepped into his bedroom wearing only a towel and found his wife sitting in the bed waiting for him.

"We need to talk babe, come sit down please." Hailey pleaded patting the bed beside her.

Anthony sat on the bed and placed his hands on his lap. He was sure it was going to be an uncomfortable discussion on why he shouldn't wear her panties and she would likely force him to promise to never do it again. He was surprised when she held a pair of blue thong panties in one hand and his plaid boxer shorts in the other though.

"Which of these would you rather wear Anthony?" Hailey said holding the underwear up in front of her.

Anthony eyed the thong panties. He could tell immediately they weren't Hailey's. Her panties were much larger. The panties she held were much smaller and looked brand new. Anthony's heart fluttered as he started speaking. Nothing would come out and he stuttered.

"I... um... the... a... the blue ones," Anthony said, dropping his head in shame.

"OK, put them on. Let's see how they fit," Haley said handing him the panties.

Anthony took the patties and started walking towards the bathroom. Haley stopped him before he made it to the door.

"If you want to wear women's panties, you're going to have to put them on in front of me," Haley demanded.

Anthony's face flushed red with embarrassment. He turned to face his wife; the blue thong panties hooked around one of his fingers and hung loosely by his side. He looked shamefully at the ground as he dropped his towel to expose his wet shriveled penis. He was becoming aroused but his penis was still somewhat small.

Anthony stepped into the thong panties and pulled them up his thin legs. The string at the back nuzzled its way between his cheeks and he pulled his ass cheeks apart to allow the fabric to seat itself where it belonged. The panties fit perfectly and completely covered his cock and balls.

"How do those fit honey, do they feel OK?" Haley asked twirling her finger around indicating that you should spin for her.

"They feel great!" Anthony said spinning a new circle for his wife.

He didn't notice her holding the bra until he stopped spinning. It was the same color blue as the panties he was wearing. His heart stopped at the sight of it, and she held it up for him to see.

"Do you... do you want to wear this too?" Haley asked looking unsure of herself.

Anthony didn't answer, all he could do was stare at the small cups of the bra. Haley crossed the room and stood behind Anthony. She flipped the bra around in front of him and held it up to his chest. Anthony pushed his arms through the straps of the bra and Hailey pulled it tight around him.

"I wasn't sure what size to get. I hope this fits you, it's so cute." Haley said clipping the bra together at his back.

Haley fiddled with the back of the bra for a moment pulling, tugging, and readjusting the straps until it looked right.

"It's just one size too big, but it will work for right now," Haley said pulling the band down and adjusting the cups over his nipples.

"That's a 36A, you'll need a 34B, but we should probably have you measured just to be sure," Haley said walking around in front of him still adjusting his bra.

Anthony stood there stunned. He didn't know where The woman standing in front of him came from. He wasn't even entirely sure she was his wife. Everything was so surreal for him. His wife had just dressed him in a brawl and panties and he was acting so natural, so nonchalant about everything.

"OK get dressed, I don't feel like cooking tonight so we are going out to eat tonight," Hailey instructed.

Anthony stepped into the closet and started unhooking his bra so that he could get dressed. Haley stopped him and said,

"You need to keep your boobies covered when you're out in public from now on okay Honey!" Haley instructed.

Anthony stopped trying to unhook his bra and left it in place. His head swam as he tried to decide what color shirt to wear to hide his bra lines. Anthony grabbed a dark blue button-up shirt off the rack and pulled it from the hanger. Hailey pulled a light pink button-up shirt he bought years ago but never wore and handed it to him.

"Here dear, wear this for me tonight please!" Hailey insisted taking the dark blue shirt out of his hands.

Anthony held the pink shirt up to the light. We could see the light pouring through the shirt and worried it would be far too see-through to hide anything. It was still quite warm outside, but if he dressed like he was going to work... he might be able to get away with wearing a sportcoat too.

Anthony stepped into his pants and put on his shoes, then grabbed a jacket and followed his wife out to the car. She had dressed up for dinner as well and wore a black body-hugging dress that ended just above her knees. She wasn't wearing a bra or panties. She simply stripped nude and pulled the dress over her luscious body.

Anthony pulled a shawl out of the closet for Haley in case she got cold later. He sat down in the passenger seat as Haley insisted on driving.

"You look very pretty in that shirt honey, thanks for wearing that for me," Haley said as she pulled out of the driveway.

"Thank you, dear, you look sexy like always!" Anthony said smiling at her.

"Thanks, baby!" Hailey replied.

They drove in relative silence for the rest of the trip into the city. Anthony had no idea where she was taking him for dinner but they had both dressed up somewhat. He just sat there enjoying the feeling of fabric nestled tightly against his asshole, and how the bra straps dug into his shoulders like a constant reminder that he was wearing a bra.

Call Halle parked in front of the local steakhouse. The parking lot was packed so he knew they would likely have to wait a while before being seated. Anthony handed Haley the shawl as he stepped out of the car.

"I'll go get us a table, you can just wait out here if you like," Haley instructed.

Anthony buttoned up his sport coat, drove his hands deep in his pockets, and milled around the entrance to the steakhouse waiting for his wife to return. Within five minutes she was standing back at his side wrapped in her shawl snuggled up close to him. The summer airhead cools considerably as the sun started setting.

"It's just a 15-minute wait, they'll buzz us when they have a table," Haley said holding a disk that looked like a hockey puck.

Hailey unbuttoned Anthony's sport coat and drove her bare arms inside his coat searching for body heat. She left one arm between their bodies and the other pulled Anthony tightly against her body. Anthony wrapped his arms and coat around Hailey's body, shielding her from the cool evening air.

Hailey played with Anthony's bra straps as he held her. She lightly pulled at the band letting it snap him on the back as she cupped his chest where the bra cup sat.

"Are you sure you're OK with this, me wearing these things?" Anthony whispered.

"Here's the deal babe, you're my husband and I love you. If that something you want to wear and who am I to tell you no?" Haley said looking up at him.

"OK," Anthony replied.

"Besides, I like women too. I can handle it if my man wants to wear lingerie, and feel pretty." Hailey added.

"It just turns out I like men who are slightly smaller, thin, and a little effeminate like you!" She clarified.

"I'm not effeminate!" Anthony protested quietly.

Haley didn't say a thing, she just looked up into his eyes well she tugged on his bra strap letting it snapback hard against his skin.

"I'll bet money that you would shave your body, paint your fingernails, and even wear makeup!" She challenged.

The puck buzzed to life, beeping and flashing in Anthony's hand indicating their table was ready. It was a welcome distraction from the direction of their conversation. It was true... he did want all of those things too. He just didn't want her to know that already.

The steakhouse was dimly lit and packed. Servers jostled past each other with trays of food and drinks. The kitchen was bustling, noisily calling out orders and dishes. They were seated in a booth near the bathrooms where the foot traffic was slightly lighter. Hailey pushed herself into the booth to sit right next to Anthony. They had a view of the whole restaurant.

"Will you give me your coat, please? It's way too cold in here for what I'm wearing!" Hailey asked.

Anthony's face must have held a look of horror because Hailey just looked at him sternly.

"Oh, you're worried about someone seeing your bra? Calm down... no one pays attention to that sort of thing, and those that do, don't care! Now I'm freezing!" Hailey demanded.

Anthony pulled his coat off and wrapped it around Hailey's shoulders. She immediately warmed up and gave him a big smile. His reward was a soft kiss on the cheek.

Their server brought a round of drinks and since Anthony wasn't driving Hailey insisted he have a cocktail to help him relax. Their service was quick with the drinks but slow with the food. Anthony loosened up after only two drinks and relaxed in the booth like he normally would as he forgot he was wearing lingerie.

"So Anthony... I'm curious!" Hailey started saying.

"Yeah, what's up babe?" Anthony asked.

"Just what kind of man do you find attractive?" Like when you see him, do you want to jump his bone?" Hailey asked pointing to a young dark-haired man thin and somewhat feminine.

"Hailey!" Anthony protested.

"What? I want to know! What kind of guy makes you horny?" She whispered in his ear.

Anthony felt good but he didn't want to go over the man he found attractive with his wife. It just felt weird to discuss other people's sexual attractiveness. He did spot a guy that he could see himself servicing. The man was walking right toward them, obviously on the way to the restroom.

He was tall and fit. The man's forearms were thick and strong. There was a tuft of hair poking out the top of his V-neck sweater vest and his slacks were fitted down to his light brown Oxford's with no socks. He looked straight but gay at the same time.

"Twelve o'clock! V-neck sweater vest!" Anthony blurted out.

He felt ashamed pointing out men that he would like to fuck to his wife, but the alcohol had loosened his tongue and he couldn't help but imagine the things that man might do to him. He would get pinned to the wall and the man would stick his tongue into his mouth while undressing him. V-neck would choke him with his cock just to get warmed up before he fucked his ass!

"Mmm... good choice, he's sexy as fuck!" Hailey cooed.

"Another question... when you're looking at the images of guys dressed up as girls, do you imagine doing things to them, or being them?" Hailey asked with a devilish smile.

"Being then mostly." Anything answered quietly looking at his lap.

"It's okay Honey, you can't control what gets you going!" Hailey reassured.

"This isn't a conversation I ever thought I would be having with my wife," Anthony answered.

"I like big Tomboys that like to take control and dominate me like one might imagine a man doing to a cute young girl. I find that to be the most appealing thing when I'm with another woman." Hailey said.

"Men, on the other hand, I like them to be like you? You're exactly my type, and I love you for it!" Hailey professed.

"Okay," Anthony said.

"So what have you done with men before?" Hailey asked smiling again.

When Anthony didn't immediately answer she asked another question.

"Have you ever had a crush on someone I know, maybe one of our friends?"

Anthony was shocked she would ask something like that! Why would she want to know something that real, that close to them?

"Oh my god! Who is it? Who do you like? Do you like Kevin?" She asked.

Anthony just looked at Hailey. He refused to answer her question, but he didn't have to say a thing. His answer was all over his face. She could tell by the smile he was trying desperately to hide. The third mixed drink had broken down any inhibition He thought he had left.

"I've always thought Kevin was hot, but I'm not gay!" He protested.

"Are you sure you aren't even a little bit gay honey?" Hailey said looking at Anthony as though she were calling him on some bull shit.

"I chose not to be gay when I met you!" He said, trying to save a little bit of face.

"We don't have to be unhappy anymore, we don't have to be unfulfilled anymore Honey, that's the whole point of all this!" Hailey offered.

"You were unhappy?" Anthony asked.

"No, I was fine but if you were happy, that would have been the first thing you said. Not questioning why I wasn't happy." Hailey said.

"We just need to establish some ground rules if you want to experiment with men." Hailey offered.

"Okay," Anthony said.

"Do you want to have sex with Kevin?" Hailey questioned.

"Who knows he even wants to have sex with me, Hailey?" Anthony asked, shocked he verbalized the question in the first place.

"You're Kevin's type to a "T!" Hailey exclaimed.

The food arrived and they both dug in obviously far more hungry than either thought. It didn't take long for both to nearly finish their plates and the conversation to continue down an uncomfortable path for Anthony.

"Kevin asked me to come over to help him with his taxes Saturday night. I'm sure I can ask him if he wants to..." Hailey leaned in close to finish her statement, "I can ask him how he feels about having sex with you!" Hailey whispered into Anthony's ear.

Anthony's heartbeat excitedly in his chest. He could barely contain his excitement and fear at the same time. What if he let it slip that they had already become sexually active? What if she found out that he already sucked Kevin's dick!