The Rendezvous Ch. 02

(Author's note: I have tried to get an editor for this story but failing that after over a week of looking I'm publishing it.

Please be aware this work has some fictional coercion and other sissification elements.)

Nick tried to hold back as tears welled in his eyes but the finally started to stream down his cheeks in black rivers. His make-up was already messed up from the deep throat lesson, eyeliner running into blush and foundation as he had struggled with the cock down his throat. The breast forms in the bra heaved as sobs started even as he tried to struggle to hold it in, not wanting to give the man the satisfaction. He wasn't even sure if he was crying because of what was done to him or because of how his body had reacted, deep down perhaps enjoying it.

Wyatt was suddenly there next to him and grabbed him by the shoulders, bringing Nick up on to unsteady legs. The man's fingers caressed his wrists tenderly for a moment before they moved to the steel handcuffs. Metal scraped against metal for a moment before he heard the loud clicks as his wrists were freed from the tight binds. Nick brought his hands in front of him to rub his wrists though he knew he wasn't free as long as the man threatened him with the video.

"Go into the bathroom and redo your make-up," Wyatt said, handing him his purse.

Nick shuffled into the small motel bathroom and was surprised to see it looked like the other man had set some things up. Glancing over his shoulder, he ignored the plastic jug and tubes before he got in trouble and moved over to the sink with the mirror above. Wetting a wash rag, he wiped the mess from his face before pulling out his make-up kit from the purse. Doing his best to steady his hand, he reapplied the make-up until he was back to how it had been before the man's lessons.

As he finished, Wyatt appeared behind him in the mirrors reflection smiling at him. "Very good. A sissy should always look her best for her Daddy. You may find the night better if you think of yourself fully as Nikki. That's what you've been striving for all these years after all."

He felt the man's strong hand on his pushing him forward to lean over the sink and forcing him to stare into his own eyes. A small gasp left him when he felt Wyatt's hands sliding up his stocking clad thighs and pushing the dress up over his hips. He told himself it didn't feel good but it was the first time anyone had touched him like that while dressed up so that was why he felt a thrill. Once his skirt was up, the man pulled down his panties sending a sharp panic through him even as his erection pressed against the cold porcelain of the sink. "Please," he begged. "Don't do that. Don't stick it in me."

A laugh came from behind him before Wyatt pressed along his back, the man's cock rubbing along his bare cheeks. "Don't worry, sissy. I'm not going to yuck you now. But before the nights out you will beg for me to fuck you hard. All we are going to do is get you ready for that moment. A good sissy should always be ready for her Daddy."

The man pulled away and for a moment he thought he was ok. Then, he felt something cool dribbling down between his ass cheeks followed by the loud snap of latex that made his whole body tense up. Latex covered fingers began to massage the strange fluid into the tight ring of muscles before slowly pushing into his anus. As he resisted, a hand slapped his ass hard causing him to yelp and suddenly a finger was sliding into him. He grunted as the invader slid in and out of him a few times. Another finger was added and he grunted louder but as it pressed deeper into him it hit something that sent ripples of pleasure through him. The fingers massaged at the spot until a moan slipped from his lips without thinking.

The fingers left him as he leaned against the sink in a stupor never having felt such a thing before. Before he could regain himself, something plastic was shoved into him and seated firmly. Nick tried to stand up but a strong hand was at his back again, holding him in place. He looked over to see Wyatt reach over to the container that hung from the shower curtain rod and twist something. His eyes widened as he realized what was happening as he felt the fluid rushing into his rectum, warming him inside. It was a weird sensation at first, a rushing of fluid that tickled almost but slowly pressure grew until it started to get a little painful, but all he could do was squirm his backside which brought another slap. After what felt like hours, the man turned the thing off and the fluid stopped filling him.

Breathing shallowly, he thought his ordeal was over when he felt the man take the nozzle out of him. But a moment later, something was pushing into him stretching the ring of muscles farther open then they had ever been before, making him cry out. He noted how feminine the echoes were as the stretching suddenly ceased as he felt the butt plug settle in, held in place by the wide ends on either end, a small piece of rubber keeping the muscles slightly apart.

"That will give you some time to let the solution clean you up since you are a virgin down there," Wyatt told him, letting him stand up. He guided him to the toilet with the lid down and set him down while he didn't resist, feeling any fight gone from himself. As he settled down, he found himself at eye level with the half hard cock of the man who inched closer until it was almost at his lips again. "While we wait, clean me up. It will give you some time to practice your skills."

Taking a deep breath, Nick looked up at the man helplessly but knew there was no pity there to be found. So, he slowly extended his tongue and licked at the head once before swirling his tongue around it, bringing an appreciative moan from the man. He could feel the smug satisfaction of Nikki in him, having made a man cum and now having made him moan some more, but it had always been a fantasy and never meant to be a reality. Reaching a hand up, he wrapped his one hand around the shaft to straighten it out as his lips enveloped the head, swirling around it and bathing it to taste the strong taste of cum still clinging to the crevasses. He bobbed his head a little as his other hand came up and cupped the man's balls, remembering how he liked to have them played with.

As he sucked on the tip of Wyatt's cock, he heard a cellphone ringing for a moment before the man reached into his pocket and pulled it out. Answering it, he was shocked when he heard who the man was speaking with.

"Hey, Barb," the man said cheerfully. "Oh, don't you worry. Me and Nick are having a ball. We just got done watching some sports at the bar and pushing back some beers. You should see him suck it down." The man winked down at him before slapping Nick's cheek because he'd stopped, the sting making him suck again. "I'm going to take him down to the strip club next, show him who should be the only one in high heels." He laughed loudly suddenly, the motion vibrating the dick in Nick's mouth. "Ok, I'll get him a lap dance on you, darling. You just enjoy your girl's night and leave the boys night up to me, I'll show your hubby the right way of things."

The call ended thought it took Nick a moment to realize he was done, his mind torn between the strange thoughts in his head and the urgency of his bowels filled with water and the embarrassment of it all. Suddenly, Wyatt pulled his head back off the now clean and shiny cock, a string of spit hanging from the head to his lips. "Well, looks like you are all mine for the night," he said, smiling at him. "I suppose you are ready to get going."

The man pulled the plug from his ass and let him empty the enema from his gut as he reapplied his lipstick once more. He packed his purse and thought he was going to get out of the bathroom when he was forced to bend over again. Despite his protest, the plug was lubed and shoved back into place before being told to take the panties off and lie on the bed. He didn't want to, but he did, glad that the ordeal had at least softened his erection so he didn't feel so messed up inside.

Laying back on the bed, Wyatt returned with some metal contraption, and moved to lay across him, his body weight pinning Nick to the bed. He couldn't see what the man was doing but he could feel him taking his soft cock in his hand and the embrace of cool metal. First there was a tightness around his sack and the base of his cock and then along his soft shaft as he felt himself man handled into something. Something clicked and when the man moved, he found himself wearing a chastity device over his cock, locked firmly in place, steel encasing his small dick except for the open slit at the end.

"Seeing as how hard you got being a cock sucking slut," Wyatt sneered. "I figured I had to take measured to keep you in check. I wouldn't want you playing with yourself and cumming in your panties. You'll get relief when I say so. Now, pull up your panties and let's get ready."

If it was possible, Nick felt more humiliated than ever as he sat up and pulled the soft panties up. The metal encasing him and the rubber plug inside of him reminded him constantly of his ordeal and his helplessness in the matter. "Get ready for what," he asked, straighten his skirt.

"Well, first we need to get you some proper heels. Those boots are not proper sexy sissy wear. Then, well, we'll see." The smile on the man's face didn't fill Nick with confidence and he felt the dread sitting deep in his stomach at the thought of having to go out dressed up and at this man's mercy. He would have protested but he knew there would be no use.

Nick started to follow Wyatt as he let himself fall into Nikki mode, putting a little more swivel in his hips with each step. The night felt cooler than when he'd gone into the motel room but it was more because of how warm he felt inside. The tight confinement of the chastity device and the constant movement of the plug distracted him enough that it was hard to be worried about anyone seeing he was a man. Worse, he kept remembering how the man's fingers had hit the special spot with every jostle of the plug, feeling a mix of guilt and wonderment.

Wyatt led him to a black Lexus sedan that honked and flashed its lights as he hit the buttons on the key fob. He put his bag in the trunk before opening the passenger's side door for him, his intense gaze on Nikki. Thanking him in a soft, higher toned voice, Nick slid into the seat as his hands moved down the back of the skirt so it was smooth and didn't wrinkle. Wyatt shut the door before getting into the driver's seat and starting the car.

Relaxing classical music streamed from the speakers as they drove through the night with Nick looking over at Wyatt every so often. He'd not had a lot of dealings with the man so he couldn't understand why he wanted to do this to him. It didn't make any sense why he wanted to force him to do these things and humiliate him like he had.

"Something on your mind," Wyatt asked without looking at him.

"Why," he managed to stutter.

"My roommate in college was a closeted sissy like yourself and I helped him explore that side of himself. After he had to move away after school was over, I deepened my interest in the subject via Craigslist. Then, at my first job I found one of my coworkers was a sissy too but he was all hung up on not being gay. So, I showed him like I'm showing you that there's a difference between being gay and being a cock craving sissy. I helped him accept what he was instead of fighting it."

"I don't crave cock."

"Please, Nikki. I saw how you reacted. You wife would destroy Nikki, destroy who you truly are, so I knew I had to act. Plus, selfishly, it's been a while since I've gotten to play with a pretty sissy."

"You think I'm pretty," Nick asked before he could stop himself.

A bright smile pulled up the corner of Wyatt's lips making him look much more handsome then his previous scowl. "I think you are gorgeous, Nikki."

They drove in silence for the rest of the way. The panic started to come back as the car pulled into the lot in front of a DSW store and parked. Wyatt slipped from the vehicle and walked around to open his door, looking at him expectantly. Taking a deep breath, Nick slipped from the seat and followed the man into the store. It was almost closing time and most of the customers were at the checkout where a pretty young woman and a handsome black male were ringing people up.

Wyatt led him down the aisle with a bunch of lovely high heels were on display, stuff he'd only dreamed of owning. He pointed out a few pairs he wanted to see on Nikki and he grabbed one of each in his size. The man surprised him by kneeling down and pulling off his boots and putting on each pair of shoes. He finally seemed to really like the black heels with ankle straps that had gold, five inch stiletto heels. Buckling the ankle straps, he stood up and took a step back.

"Can I help you," the clerk from up front asked. She had long brown hair and a lithe figure that was outlined in a tight fitting dress, though the hem wasn't high enough to call slutty. While she didn't have ample breast the dress displayed her B-cups rather nicely. She wore strappy black sandal heels on nylon clad feet that was enough to give Nikki envy. "We are closing up here."

"Sorry," Wyatt said, flashing her a smile. His words were as sweet as honey as he stepped closer to her, his eyes carefully looking her up and down. "My friend here is trying on some heels for the first time and I'm just trying to help support him. Seeing as how well you wear yours, perhaps you could help and get us out of here faster."

The woman looked at Nick with wide eyes as she looked him over as he teetered on the heels. She stepped closer until she was almost in front of him, a strange smile coming to her lips. "So, are you two..."

"Oh, no," Wyatt answered. "I like my women. But you have to support a friend no matter what he's into, right."

The woman beamed a smile as she looked over at the man and looked him over with a new appreciation before returning her attention to Nick. "Well, the thing to remember is it's a balancing act and a matter of how you put your foot down. Walk with me." She took his hand and helped him struggle down the aisles as she instructed him what to imagine for balance. He could see the man's snarky smile as he watched the two dressed up so lovely walking back and forth until it seemed like Nick got it and was walking without holding onto anything or looking like he was going to break his leg.

"What's going on, Missy," the black clerk asked, walking back after locking the front doors. "We need to shut up." He looked impatiently at the two women before realization slowly came over him, sparing a glance over to Wyatt.

"Sorry, my friend needed some instruction," he started, walking over to the man. "I think we are ready to take these shoes. But if you'd like a tip for being so patient, I'm sure Nikki here would be glad to make your extra time enjoyable. He confessed to me how he has sucked off a few guys but has always wanted to enjoy a black cock."

A long silence hung in the air between them as they all looked at one another, the muscles in Nikki's jaw jumping but not saying anything as he remembered the tape. All three men were surprised when it was Missy that finally spoke up. "Come on Harris," she said in a warm voice. "You always complain about how your girlfriend won't blow you and look at her, ready to please you. Let's have some fun."

Harris looked towards the front but the shades had all been drawn over the glass front windows and the light turned off at the entrance. With the doors locked, they wouldn't be disturbed or spotted. "Ok, the cameras are off anyway out front here." He reached down and unbuttoned his black slacks and slid them down his muscular thighs, stepping out of them and his shoes. With just black socks and a button up lavender shirt, he took a step forward as he reached down and wrapped his fingers around the growing erection. "Come here, baby, get your first taste of black meat."

Nick started at the growing thick club of a cock the man held, her eyes wide as she thought about having to tackle that. She glanced over at Missy who smiled and motioned for her to go ahead. Then she looked at Wyatt and saw the expectant look, knowing he didn't have a choice. Slowly, he walked over and knelt down in front of the black man, reaching out to wrap her polished fingers around his cock, amazed at how soft it felt as it slid into his grip.

It pulsed and grew harder as he moved his hand up and down the length for a moment. Leaning forward, he lapped at the head as fluid began to leak from it, surprised at how different it tasted from Wyatt. Slowly, her lips slide up over the helmet until her lips were wide and finally slipped around the rim, her tongue struggling to swirl around it as it stretched her jaw. He had to concentrate more on the glans on the bottom as his lips wrapped tight around the shaft, moving slowly up and down. Her hands started to slide more aggressively up and down the shaft as she did, wanting to get this over with as her gut twisted inside.

A moan left Harris as his cock grew as hard as steel in his mouth, bringing up her other hand to play with his balls. The texture was so different he thought as her tongue pressed along the bottom and her lipstick covered lips sucked at the shaft. The brown shaft glistened like mahogany he thought when he'd pull back and it was coated with his spit, gathering it to help her hand jerking him off.

Out of the corner of her eye, he saw Missy with her dress hiked up and Wyatt with his hand down her panties as she leaned back, her lips parted and breathing heavily. A blush was on her cheeks as she realized the woman was getting off on watching him suck her coworker's cock. Pain lanced through him as the chastity device grew too snug as he realized his body was growing excited with everything. Keeping him from even getting fully hard, it seemed to only stoke his desire for relief.

"Show him that deep throat technique you always rave about, Nikki," Wyatt called out, smiling over at him.

"Yeah, slut," Harris added, his hips moving more. "Show me your skills." One strong hand cupped the back of Nick's head and pulled him down on the throbbing cock until the fat head wedged in the back of his throat. He tried to remember Wyatt's lesson but the cock in his mouth was only the second he'd sucked and it was even bigger than the first. He tried to deep throat the duck but the helmet wedged in his throat causing him to choke. Saliva coated the shaft and dribbled down his chin as he pulled back, thick strands clinging to the head and his painted lips.

"Such a lewd bitch," Missy said, her eyes half lidded with pleasure.

Before Nick could say anything, Harris shoved his erection back into his mouth and drew it down its length. He worked his hands and tongue more urgently in hopes of getting him off before he passed out. As his lips engulfed as much as he could, he reflected on how much different Harris was from Wyatt in taste and texture. Harris was smooth and soft to his touch like velvet while Wyatt's monster was veiny and rough. Perhaps it was in his mind but the cock in his mouth tasted tangy with a little sweetness where Wyatt has been salty and almost tart, for lack of a better word.

With a groan, Harris shoved his cock as deep as it would go as the shaft pulsed between his lips. He felt the cum spurt against his throat making him swallow it all down and fight his gag reflex. After the first few shots, the man's grip loosened enough to pull his head back and take the remaining streams of seed on his tongue before gulping it down. He could feel eyes on him and didn't want to incur Wyatt displeasure even if he let the white pools of flavor sit on his tongue a little longer than he had to before drinking it down.