The Deal

Carolyn slowly slid her full lips from the base of her husband's cock to the tip, letting it pop from her wet mouth. "Well, what's it going to be?" she asked.

Freddy's eyes rolled back in his head. He had been pleading with his wife for anal sex for over a year. She had always flat-out refused but today she proposed a deal.

"Seriously?" he asked, "you want to dress me up like a woman?"

Carolyn painted a long, slow lick along his shaft. "Yes," she grinned, "you let me dress you up and you can have whatever you want, baby. Ass-fucking, role-playing, anything!" She licked him again. "Deal?"

Freddy groaned. The thought of his hard cock buried in his wife's ass would be worth it. Besides, what harm could there be in dressing up?

"Yes!" he exhaled, "yes! Whatever you want!"

Carolyn smiled. He has no idea what he's in for, she thought.

Dressing Up

Carolyn insisted that she go first. She would dress her husband up however she wanted, and if he cooperated he would get a hot ass-fuck.

When Freddy walked into the bedroom his jaw dropped. The bed was covered in expensive-looking silky and lacey garments and accessories. "Come on baby," she called from the bathroom, "we're going to start in here."

Carolyn directed Freddy to strip down and step in the tub. After getting the warm water running she poured hair remover into her hands. "No way!" Freddy protested when he saw the label and stepped away.

Carolyn glared at him. "Listen!" she shot back, "remember our deal? No arguments or it's off! Understand?"

"But-"

"No buts! I'm not going to negotiate on every little thing. You promised 'complete cooperation,' remember?"

Freddy nodded.

"Right," she confirmed. "Do as I say or kiss that ass-fuck goodbye. Are we clear?"

"OK," Freddy agreed sullenly.

"Good," she affirmed as she began to rub the cream over his hairy chest. Freddy closed his eyes, thinking of the ass fucking that was going to take place. Carolyn began on his upper body, gentle but firm, working her way down to his feet and back up. After the cream had time to soak in she turned the spray on her foamy husband and washed him smooth with a washcloth.

Freddy' eyes went wide and Carolyn gasped as the water revealed Freddy's bare skin. She had never seen him like this. Freddy couldn't remember when he didn't have body hair. It looked strange. Carolyn smiled as she ran her hands over his smooth chest. "You look sexy baby."

After the hair remover Carolyn carefully shaved her husband's balls and down to the crack of his ass, applying shaving cream and gently running the razor over his most sensitive areas. To his surprise, he started to get hard as his wife worked the razor over his balls. "Careful baby," she giggled, concentrating intently on the sharp metal against his wrinkled scrotum. After she shaved his armpits and face she applied a fresh-scented powder. "You're smooth as a baby!" she declared.

Freddy shuddered as Carolyn dropped to her knees, toweling off his legs and applying more powder. She couldn't get over how smooth he was. She couldn't resist running her tongue along the smooth skin of his belly, licking him softly as she kneeled before him. Freddy couldn't believe how sensitive his hairless skin was - her tongue felt hotter and wetter than ever before.

"Mmmm," Carolyn purred as her tongue reached his freshly shaved pubic area. She took his growing cock in her hand as she painted soft, little licks along the length of his shaft and down to his hairless balls.

"They're so smooth" she moaned. Freddy moaned too. Her licks sent jolts of electricity through him. "Mmmm, it all looks so pretty," she cooed, inspecting her handiwork. "Unfortunately baby, you can't come until later. We still have lots of work to do."

"But-" Freddy began but then remembered their deal. Carolyn giggled and led him into the bedroom.

Dressing Up

Everything was laid out for him. Carolyn had been secretly planning, taking note of his measurements and carefully selecting his outfit. Freddy was mortified. Here he was, in his own bedroom, completely nude, clean-shaven, and about to dress up in women's clothes.

Carolyn picked up a pair of frilly red panties and handed them to her husband. Resigned to his fate, Freddy slipped the silky garment up his legs and snugged himself into them. To his amazement they fit and even had a pocket to tuck away his semi-hard cock. Freddy looked at his reflection in the mirror wearing nothing but red panties. He took a deep breath.

Carolyn helped him step into a pair of sheer stockings, then slipped him into a short white skirt with ruffles. Carolyn zipped him up and smoothed it out, hiding his tell-tale bulge in the ruffled fabric.

"Not bad," Carolyn said. Freddy had a slim runner's build and looked wonderful in stockings and short skirt. "Not bad at all," she said again, admiring the smooth curve of her husband's well-toned calves. Freddy looked from the mirror to his wife and saw fire in her eyes. She was loving this. He took another deep breath and prepared for his fate. He figured he'd prance around the house a bit and she'd be satisfied.

Freddy was intrigued when he saw that Carolyn had purchased top-of-the-line silicon breast forms. He hadn't considered that realistic tits would be part of the outfit. "These will make you about a C cup," she explained. "Now hold up your arms."

Freddy did as he was told, getting strangely aroused as he stood there in a short skirt and stockings while his wife applied adhesive to his hairless chest. She pressed the silicon forms against him and held it for a few minutes. When she let go it was like he had real female breasts. They were full and firm, with perfect shape and pointy nipples poking out from each mound. They felt and looked like part of his body, moving with him in a perfectly natural way. Carolyn smoothed out the edges with makeup and clasped a sheer, lacy bra around her husband's new boobs, clipping it in the back.

Carolyn pulled his arms out and slipped him into a sheer, light blue ribbed cotton top with buttons down the front. It was tight, revealing every contour of his new bust.

Carolyn undid the top few buttons to expose a hint of her husband's lacy white bra. "There!" she exclaimed, "what do you think?"

Freddy couldn't believe it. He marveled at his new shape, looking down at the cleavage rising from his chest and hard nipples poking through the thin blue shirt. He turned to the side, looking at his new curves in the mirror, then another turn to look over his shoulder at his rear, the frilly white skirt framing his now-shapely ass and his long, lean legs. He gasped, loving the feel of being dressed in women's clothes, of having a womanly shape.

Carolyn was feeling the same way. Her husband looked even better than she had imagined. They were both incredibly excited now, the kind of excitement you get only when experiencing something for the first time.

Next Carolyn began on her husband's makeup. She lightly brushed the skin of his face and added blush to highlight his cheekbones. She did his eyes, making his lashes long and thick and adding color. She painted his lips a wet, glossy pink, then stood back to study her work.

"Can I see? Can I see?" Freddy asked.

"Not yet," she whispered as she pulled a wig from a box. It was strawberry blonde and shoulder length, increasing Freddy's level of delight. He was always dropping hints for Carolyn to color her hair but she never did. It never crossed his mind that he would be the one to make his fantasy come true. Freddy was going to be a hot, sexy redhead.

"Almost there," she cooed. After brushing the wig out just right she picked nail polish to match his pink lips. Freddy sat patiently as his wife pressed long nails onto his and began applying pink polish to each of them. His cock was as hard as a steel pipe under his skirt. Carolyn took her time, carefully painting each nail. With his smooth skin and pink fingernails his hands struck him as looking quite feminine, like a girl's hands. He had always loved watching a woman stroke his cock with long, painted nails. Carolyn had stroked him to many an orgasm with her manicured fingers.

Caught up in the moment, Freddy wondered what his pretty hands would look like stroking his own cock and then, to his surprise, he wondered what they would look like stroking a really big cock - someone else's cock. Freddy imagined a long, thick shaft wrapped in his dainty, polished, pink fingers. He shuddered.

His thoughts were broken when Carolyn clapped her hands in delight. "Beautiful, baby! Almost done!" She clipped large, silver hoops to her husband's ears and studied his face, touching up his lipstick and getting his hair just right. Finally, she smiled. "Done!" She led her husband to the mirror and he almost had a heart attack.

"Oh, my God!" he gasped, "I can't believe this!"

"You like?" she giggled.

"Wow," he responded, "if I wasn't married I'd try to fuck me!" Carolyn laughed, proud of her work.

Freddy couldn't believe what he saw. He was hot. The eye makeup and highlights gave him a sensuous, feline look and his hair was luxurious. His lips were wet and plump, shimmering in pink gloss, just waiting to be kissed. He had ladylike curves and full, firm tits tightly encased in the thin shirt, leaving nothing to the imagination. It was amazing. His nipples were poking out. His makeup was just right.

Carolyn pried him away from the mirror and strapped his feet into a pair of sexy shoes with ankle straps and two-inch heels. She had decided not to go too high on the heels as she had big plans for the evening. She didn't want him falling down every time he tried to walk.

"Here," she said, "practice walking in these and try talking in a high voice. I'm going to go get ready as fast as I can."

Ready for what? Freddy thought. They weren't really going out, were they? But before he could protest she was already in the bathroom with the door closed behind her. Freddy remembered he wasn't supposed to protest anyway, so he resigned himself to follow his wife's instructions.

Freddy put the shoes on and they fit perfectly. He looked at himself in the mirror again, amazed at his appearance. He noticed a bottle of perfume on the dresser and thought, why not? He game himself a tiny spritz on his neck and in his cleavage. Freddy was beginning to embrace his new persona and couldn't wait to take the next step, whatever that might be.

Carolyn soon came down the stairs wearing a short black skirt, tight white top and 4" heels. Her legs seemed to go on forever and her firm tits were clearly visible through her thin white blouse.

"How do I look?" she asked, giving a quick twirl for Freddy who nodded his approval.

"Well," Carolyn giggled, "I didn't want you get all the attention."

Freddy laughed, drinking in his sexy wife. Standing next to him, she pointed to their reflection in the large mirror in their hallway. She hooked her arm in his and leaned into him, purring seductively, "well, baby, two hot ladies like us can't just stay home, can we?"

Freddy looked at her dubiously. "You're joking, right?" he replied, hoping she was only kidding.

Carolyn bit her lip and shook her head. "Uh-uh, baby. Trust me. It'll be fun."

"Really?" Freddy responded in a panic. "You want me to go out like this?"

"Of course, baby! That's what hot girls do, right? What's the point of staying home?"

"But-" Freddy began before Carolyn put her finger to his lips, cutting him off.

"Don't worry baby. You look hot! Everything's going to be just fine, trust me . . ."

The Club

Carolyn handed the keys to the valet as they strode toward the bustling entrance of the club. She heard about it from one of the divorced women in her office. It was part of a large downtown hotel and was supposedly the wildest place in town.

When the doorman saw the two hot ladies he opened the velvet rope and the crowd parted like the Red Sea. "Follow my lead, honey," Carolyn said as she took her husband's arm and stepped through the door.

Heads turned when they entered. Freddy could feel eyes roving over his scantily clad body, not just the men but the women, too. Even in a room full of hot ladies Freddy and Carolyn stood out - tall, fit and dressed to thrill.

"Two gin and tonics," Carolyn ordered as they stepped up to the bar. Freddy stood awkwardly, surveying the scene. "Ready to party, baby?" she giggled when the bartender set two large glasses in front of them.

Freddy welcomed the alcohol, taking a long gulp. The club was dark and crowded with loud, pulsing music and flashing lights. Everywhere he looked Freddy was receiving furtive glances and outright stares. He was very aware of his skimpy outfit.

Carolyn noticed her husband's discomfort. "Don't worry baby, you look hot. Own it!" Freddy tried to relax, downing his drink quickly. When the bartender brought a second round he took another big swig and felt himself adjusting. He was getting lost in the alcohol and music and swirling lights. He was starting to get used to the feel of eyes on him, taking in his long legs and flowing hair.

"I think that guy likes you, honey," Carolyn giggled, pointing across the room. Freddy shushed her, but from the look on the guy's face he thought she might be right.

"If he only knew," Freddy replied, and they both laughed. That was all the encouragement the stranger needed and he quickly moved toward them, joined by his friend.

The men were young, tall and handsome. They wore stylish slacks and fresh button-downed shirts with their biceps bulging. They looked like pro athletes. One had blonde hair and the other a shaved head. Even with Freddy and Carolyn in high heels the men stood a full head taller than them.

"Buy you ladies a drink?" the bald one asked.

"Sure!" Carolyn blurted out before Freddy could respond, "we'd love a drink!" Freddy shot daggers at her with his eyes but she just smiled back, raising her eyebrows encouragingly.

"I'm Cal and this is Jake," the bald one said as he gently took Freddy's hand. Freddy shuddered when he looked down and saw his dainty, painted fingers engulfed in Cal's strong paw. He had never felt this way before. With Cal towering over him and his pretty hand in Cal's grasp he felt . . . feminine. Not knowing what else to do, he smiled at Cal and brushed his hair back from his face.

"Nice to meet you guys!" replied Carolyn as Jake took her hand. "I'm Carolyn and this is - Freddi!"

"Freddi?" Cal asked.

"Short for Fredrika," Carolyn explained.

Jake held up his glass. "To Freddi and Carolyn!" he toasted.

"Would you ladies like to dance?" Cal asked.

"Ummm," Freddi began in his high voice, searching for an excuse.

"We'd love to!" Carolyn gushed, setting her empty glass down on the bar. She offered her arm to Jake who smoothly led her toward the crowded dance floor.

Freddi stood there like a deer in the headlights, scrambling to finish his drink as Cal took his arm and followed behind Carolyn and her new partner. "You look beautiful tonight, Freddi," he said, leaning down to Freddi's ear to be heard.

"Ummm - thank you," Freddi replied, stepping awkwardly on his heels.

With his wife leading the way, Freddi had no choice but to dance. He was incredibly self-conscious at first, but three stiff drinks were wearing down his inhibitions and he soon lost himself in the music, swayingS to the beat in the shadows. He noticed that Cal was a very good dancer, strong and graceful, a big smile on his face as he focused all of his attention on "Freddi."

Freddi realized Cal was genuinely attracted to him. Suddenly it was very exciting to be dressed as a woman, wearing jewelry and makeup, long hair and high heels, dancing with a large, handsome man, being admired.

Freddi and Cal danced two songs, and when a slow song came on Freddi was shocked when Cal pulled him close, wrapping his arms around him and swaying affectionately. Freddi was buzzed from the gin and his feet were hurting in his heels, so moving slowly in Cal's grasp actually felt pretty good, he realized. Freddi took a deep breath and decided to go with the flow, draping his arms around Cal's shoulders and melting into his grasp.

With his head resting against Cal, Freddi looked over and saw his wife slow dancing with her partner, too. She smiled at him. Freddi was getting comfortable now, starting even to enjoy slow dancing with Cal, but alarm bells went off in his head when he felt the large man's hands sliding down his back all the way to the ruffles of his skirt. Cal was holding Freddi firmly in his arms and boldly fondling his ass right there on the dance floor.

Freddi looked to his wife with alarm. He was hoping she would somehow extricate him from this situation, but he saw only excitement in her eyes. Freddi didn't want to cause a scene so he decided not to protest, and after the momentary panic subsided he realized Cal's hands on his butt felt good. It was sexy being dressed as a woman and fondled by a strong, young man. He shuddered and buried his face in Cal's shoulder, delighting in the feel of the pulsing music, his body pressed up against his partner, and Cal's soft touch on his behind.

Freddi turned to look up at Cal. The big man looked down at him and tightened his grip on his ass cheeks, pulling him closer and pressing something long and stiff into Freddi's belly. Freddi was shocked. He couldn't believe Cal was grinding into him, but again, instead of pulling away he just nestled his face into Cal's neck and continued swaying to the music, adjusting his body to snuggle up against Cal's erection.

Freddi felt deliciously naughty pressing himself against Cal's boner, imagining what it looked like, when suddenly he remembered that his wife was dancing close by. When he raised his head to look for her he got the surprise of his life. Carolyn was grinding against her partner and craning her neck up to him, their lips pressed together in a deep soul kiss on the dance floor. Freddi's eyes went wide as he saw his wife's mouth open against Jake's, their tongues dueling together, their groins moving in sync. Jake was practically dry-humping her right there on the dance floor. Cal saw it too and held Freddi even tighter.

When the song ended the two couples stood side by side, the air crackling with sexual tension. "Look!" said Jake, "there's a booth opening up in the back." The men took their ladies by the arm and led them to the dark corner of the club. Cal ordered another round of drinks as the foursome slid into the round booth, with the ladies in the middle flanked by their new friends.

Carolyn held up the conversation with the boys, who explained they were college buddies who played on the football team and were back in town to watch a game. Freddi was now pretty buzzed, and he found himself having a good time listening to the guys' funny stories.

Carolyn's was snuggled up against Jake in the dark booth, and when she saw she had Freddi's attention she deliberately placed her hand on Jake's knee. Cal noticed it too. He slid closer to Freddi and draped his hand around his shoulder. As Carolyn rubbed Jake's leg Cal pulled Freddi toward him and slid his fingers along Freddi's neck, sensuously caressing his smooth, perfumed skin. Freddi was speechless, looking desperately into his wife's eyes for something - shock, outrage - but instead he saw only excitement. She nodded encouragement and leaned into Jake for another wet kiss.

The booth was heating up, with Cal massaging Freddi's neck and Jake and Carolyn making out. Freddi could see Carolyn's tongue swirling against Jake's. At the same time, he noticed how erotic Cal's touch was - his strong hand moving gently over Freddi's skin, his large body looming over him in the dark booth. Cal was holding Freddi tight and rubbing his neck, then he raised Freddi's hand to his lips and kissed it sweetly. Cal looked deep into Freddi's eyes as he massaged his neck and covered his hand in tender kisses. Freddi was melting under Cal's touch. He was even more aroused than he was on the dance floor.