An Unconventional Convention Pt. 03

The other two couples at their table were acquaintances of the Morgans but Harry had never met them. At Carl's insistence, Kelly sat next to him with his wife on the other side, and in boy-girl, boy-girl fashion, Harry was on Kelly's right.

As dinner was served and a string quartet played light background music, the conversation around the table was pleasant, and Kelly fit in beautifully. Harry found himself amazed and impressed with Kelly's ability to answer every question asked of her without hesitation, even though he knew her answers were all fiction. Was she really that good at thinking on her feet or had she rehearsed this alternate life in her head the way she had practiced with her heels? Maybe she would make a good spy. Something to consider for that novel.

After the dishes were cleared away, a more lively four-piece band came on and began playing dance music. Not sure how comfortable Kelly was going to be dancing in her heels, Harry asked her—loud enough for others to hear—"How's your ankle? Are you going to be able to dance or do you want to just let it rest?"

Kelly smiled at him, and said, "Oh, it's fine now, Harry. Thank you for asking. I would love to dance!"

Holding her right hand in his left, with her left hand on his shoulder, and with his left on the small of her back, they danced in the old-fashioned way. As they glided across the floor to "Moonlight Serenade," Kelly said, "Thank you for offering that excuse not to dance in my heels, but I've been practicing since I got your email about coming here tonight."

"And it's paid off," Harry said. "You're like Ginger Rogers; she said she could do everything that Fred did but backwards and in high heels." They did a flourishy little turn, which she executed gracefully and flawlessly, and he went on, "Carl is going to ask you to dance; I know him. Are you going to be okay being that up-close-and-personal with him?"

"I think I'll be okay," she answered. "We've been shoulder-to-shoulder at the table for the last hour; I think I can deal with cheek-to-cheek." She chuckled, and added, "And you're right about him being an old lecher; I don't know how many times he's commented on my lovely gown while staring at my cleavage. I'm a little surprised I haven't felt his hand on my leg under the table. But I think he's just having fun; I think he's probably pretty harmless."

The song ended, and the band went into the much more lively "Chattanooga Choo-choo." Hardly missing a beat, Kelly went right into swing mode and executed spins and turns as they danced that had others besides Harry impressed.

They sat out the next song, "Harbor Lights," but when the vocalist started singing, "My love must be a kind of blind love; I can't see anyone but you ..." Kelly took the initiative, turned to Carl, and said, "Oh! This is 'I Only Have Eyes for You!' I love this song. Dance with me!" She looked across at Sylvia and added, "You don't mind if I borrow your husband for a dance do you?"

"Just don't hurt the old goat," she replied. "We'll swap partners. I haven't danced with Harry since we were here last year."

On the floor, Kelly clasped her hands together on the back of Carl's neck, allowing him to put both of his on her lower back ... her lower lower back.

"Your friend Kelly is certainly charming," Sylvia said as she and Harry swayed across the floor. "Or should I call her Tootsie?" she added with a little chuckle. "You do know that she's a drag queen, don't you?"

"Crossdresser," Harry replied. "If she was a drag queen she'd be dancing with you, not Carl, just to show off."

"I stand corrected," Sylvia said with a laugh. "I actually knew she wasn't a queen; I was just trying to get a rise out of you. I was guessing transgender, though."

"Nope," Harry said. "She's just like your run of the mill super-hero with an alter-ego-secret-identity. Only she can't get changed in a phone booth."

"So, are you turning gay?" Sylvia asked.

"Nope. And neither is Kelly," Harry replied. "That's not what crossdressing is about, normally. Although I had that same misconception when we first met six or seven months ago."

"Educate me," Sylvia said. "I grew up in the 60s, so I'm as open minded as anyone and probably more than most. Hell, I'm happy to see my husband dance with another man and put his hands on his ass."

"Well, I'm probably going to use a character based on Kelly in my next novel," Harry said, "so as usual, I've done some research into crossdressing."

"So, drag queens fall under the category of fashion crossdressers," he went on. "They don't even try to pass themselves off as women. With the exaggerated wigs, the garish makeup, and the loud clothes, it's all about the show for them; it's theater.

"Then there are those for whom female clothes are an erotic fetish," Harry continued. "The sight, feel, even the smell of a woman's clothes—especially undergarments—is sexually arousing. Sometimes they just handle and smell them, other times they wear them, but it is almost always for the purpose of masturbation. But that's not Kelly, either."

Sylvia said, "You really have done your research. Go on professor; I'm intrigued."

"Well, since the band's not playing 'In-A-Gada-Da-Vida' I'll cut to the chase," Harry replied. "Kelly has no desire to not be a man; he'd just like a respite from it once in a while, and that's probably the most common reason that men give for their crossdressing. They want to feel sexy in the way that a woman does; they want to openly cry when Jennifer says, 'Love means never having to say you're sorry.'" He nodded toward Carl and Kelly, and went on, "They want to feel appreciated by an old guy slipping his hands onto their ass while they dance. It's about leaving the pressures and demands of their masculine side outside and just enjoying life for a while."

As the band reached the final notes of the song, Sylvia asked, "So, there's no sexual piece to Kelly's puzzle at all, huh?"

Harry grinned at her and said, "A gentleman never tells. But it's not unheard of for a crossdresser's feminine side to want to explore the pleasantries of womanhood beyond dancing backward in high heels."

She laughed, and said, "Oh, to be a fly in the wall when you two get home."

"So, what tipped you off?" Harry asked as they walked back to the table.

"Her wedding band," Sylvia answered. "Or lack thereof. She told us that she's been divorced for four years, but there's a fresh mark on her finger where a ring had been recently and for a long time. And the mark is a lot wider than a typical woman's wedding band." She laughed, and added, "From there, I just took a wild-ass guess and you confirmed it for me because you thought I already knew."

Harry laughed, and said, "And that's why I'd make a terrible spy regardless of how good I look in a tux." Then he asked, "You're not going to out her, are you?"

"Oh, good heavens, no!" she answered. "It's all the more fun for me being on the inside and seeing her fool all the others! Especially Carl! He'll probably want a blowjob when we get home after dancing with her and touching her behind."

"Will he get it?" Harry asked.

Sylvia grinned and answered, "A lady never tells."

He replied with a laugh, "Yeah, I had that coming!"

The band took a break and the MC began talking about the charity that everyone was there to support. Next, a comedian came on and did a roast sort of routine taking humorous and often ribald shots at a number of the well-heeled men and women who attended the gala every year and whose donations were well appreciated.

"And there's Carl and Sylvia Morgan," the comic said and the couple waved while they got a round of polite applause. "Just saw Carl out there dancing with his daughter. We haven't seen Carl moving that erect in years!" The audience laughed and applauded, and then the comic went on, "Who else would like to dance with his daughter? What do you say? Fifty dollars a dance for charity?"

The crowd laughed, but also voiced their approval.

Kelly's mouth hung open and Harry leaned in close to her ear, and said, "Hey, I'm sorry about that! They've never done that here before. You want me to give him the ankle excuse?"

Before she could answer, the comic then said, "But I've obviously gotten ahead of myself, haven't I?" Looking at Kelly, he said, "What do you say? You danced with Carl for free, how about taxi-dancing for charity?"

Kelly smiled at Harry, and said, "In for a penny, in for a pound." She turned to the comic, and answered loudly, "Since it's for charity, let's make it a hundred dollars a dance."

The audience approved the rate increase, and the Comic called out, "Who else can we get to dance for charity?" Several women's hands went up, and he added, "Come on, guys! The women here have hundred-dollar bills, too! Or they can get them from their husbands."

When the band came back, there were half a dozen good-looking young men in tuxes and attractive women in gowns gliding and swinging around the floor with the other attendees, and they collectively brought in another twenty-six hundred dollars for the cause.

At the end of the night, after they had all said their goodbyes and Kelly and Harry were waiting for the valet to bring up the convertible, Harry said to her, "I didn't want to make you self-conscious in there, but Sylvia figured out your secret."

"I know. We met on the way to the lady's room," Kelly said. "She's really quite sweet, isn't she? She made Carl pay for his dance even though it was before they were charging." She looked at him, and added, "She said she was going to give him a blowjob when they got home, and asked if I was going to do the same for you."

Harry laughed and said, "Yeah, Sylvia can be a little bold. So, what did you tell her?"

Kelly smiled, and said, "That a lady never tells."

***

When they got home and before she went to freshen up, Harry told her, "Don't change, okay? Don't even take your jewelry off. I want to dance some more just the way you are."

When she came out a few minutes later, he had cued up an LP on his turntable, and he let the needle down onto the track. He took her hand and as Johnny Mathis began singing "Misty," he led her into the middle of the living room floor. Holding her closely in the old-fashioned way, they began swaying gently to the music while he sang along softly next to her ear.

As they moved, Kelly could feel the hardness of Harry's erection against her leg. She had felt it earlier in the evening when they were dancing at the gala, and it had made her feel sexy to know that she excited him by just dancing with him. His erection was much more pronounced now, however, and she was sure he had taken off his underpants while he was waiting for her.

He slid his hand down her back and onto her ass. Earlier, in public on the dance floor, he had given her ass a brief, but deliberate brush. The simple naughtiness of it had made her smile and had aroused her. Oddly, she hadn't had the same reaction when Carl had touched her behind while they danced. Perhaps because he was just a dirty old man acting out some fantasy. With Harry, it had been a promise of things to come. She ground her hips harder against his, enjoying the feel of his nearly unrestrained erection.

They were cheek to cheek and he moved his head so he could kiss her ear and trace its curves with the tip of his tongue. She purred and moved her hand from his shoulder to the small of his back to pull him tighter. He hummed contentedly as she squeezed his boner between them and rocked her hips to stroke it.

He let go of her hand, and as she moved hers to his back, he raised both of his to hold her head gently between them. With their hips pressed together, trapping his erection between their bodies, he gave her a ravenous, passionate kiss. Their lips moved hungrily against one another and their tongues danced while the music played.

When they broke the kiss, he separated his body from hers slightly, and said in his Bond voice, "Pull down my fly, Moneypenny. Take out my cock. We've waited far too long for this."

She smiled at his playfulness but had been thinking about doing the same thing, herself. But she liked it when he told her what he wanted; what to do. Not needing to be always in control, being able to be a bit submissive, to be dominated just a little bit was one of the things she enjoyed about being Kelly. Her arousal increased as she leaned in and kissed him while she reached for his fly.

She pulled it down and reached in to take hold of his erection. It was hard and hot to the touch, and when she slid her fingers forward, she felt the wetness of his pre-cum. She smiled knowing that she had caused it; that she could get him that aroused while still fully clothed.

With her fingers over his knob to protect it from the zipper, she maneuvered his unbending erection out into the open. He had loosened his hold on her head, and she looked down between their two bodies while she slid her hand up and down the length of his now-exposed boner.

"My balls, too," he told her. "Take out my balls, as well."

She gently drew them out, and as she had the first night they'd been together, she found the sight of his white cock and balls displayed lewdly through the fly of his black tux pants to be erotic beyond all logic. She wanted to go to her knees and take him in her mouth, but even more, she wanted him to tell her to do it.

He tightened his hands on her head once more and held her so he was looking directly into her eyes. "Suck my cock, Kelly!" he said quietly but firmly. "I want to feel your mouth, your lips, and your tongue all over my stiff cock!"

He kissed her hard, and then let go of her head and she lowered herself to the floor.

Kneeling, she looked, once more, at his rigid cock sticking out with his fat balls through his tuxedo fly. She imagined herself about ready to give James Bond a blowjob, and her arousal spiked, yet again.

She opened wide and leaned forward, taking two-thirds of his cock into her mouth, but not touching it with her lips or even the insides of her cheeks, but only allowing her tongue to slide along its underside to keep centered. She took a couple of breaths, forcing warm air over it as she exhaled, and cool air across it when she inhaled.

While he looked down at her, she closed her lips and sucked, causing her tongue to press harder and her cheeks to hollow against the fat cock. As she pulled her head back, drawing her mouth off of his dick, he let out a low moan, followed by "Oh, fuck, yes!"

She reached her hands around him and held onto his ass, then looked up at him, and said, "Guess what else I've been practicing." Without waiting for an answer, she leaned forward, and in one slow push, she shoved his cock all the way down her throat.

"Oh, Jesus!" he moaned. "Holy shit!"

She pulled just as slowly off of his dick and tilted her head back to look up at him again, and with its wet cock-head resting against her chin, she asked, "Do I get a star for keeping up with my lessons?"

"Fuck, Kelly, you get a star, the sun, the moon, and all the frigging planets!" he replied. "No one has ever done that to me before!"

She smiled, and said, "I've come to like being your first at things." She then took his cock back down her throat and as she gently massaged his balls, she bobbed up and down the full length several more times.

After a little while, switched up, and she wrapped her hand around his cock and began to slowly stroke him while she sucked on his fat knob and played with it with her tongue.

She glanced up at him and saw that he was looking down at her with a smile on his face, enjoying her "knob-job." As she sucked his cock-head, he reached down and lowered the zipper on the back of her gown about halfway. He then spread the two halves over her shoulders and pushed the top of the gown down her arms. He pushed it far enough that she was forced to release his cock and balls from her hands as her arms became trapped at her sides in the bunched-up gown. It was also far enough to fully expose her bra and her natural cleavage. In all of that, she never let his cock slip from her mouth.

With her arms "restrained" by her gathered gown, he reached down and took over stroking his cock while she serviced its big squishy head with her mouth. As he jerked off, slowly but with a tight grip, his fist pressed against her lips with each forward-stroke, and she sucked harder and clamped her lips even tighter to make sure her mouth wasn't pushed off of his cock-head.

As he stroked his cock clamped in her mouth, he reached down with his other hand and gently caressed her cleavage, tracing a finger through the cleft between her tits.

As he explored her tits he picked up the pace of his stroking to full-on jerking off, and she hungrily sucked and lapped his cock-head helping to draw out the hot cum that she desperately wanted to feel squirt into her mouth, then taste and swallow.

Suddenly, though, he pulled his cock from her mouth with a pop! and said, "Not yet! Let's save that for a little later." He seemed to be talking as much to himself as to her.

He gently cradled her head with both of his hands and helped her back to her feet. He kissed her hard, swirling his tongue with hers, looking for a taste of his own cock; his pre-cum. If there was any lingering in her mouth, it was barely perceptible; he would have to wait if he wanted more.

When they broke the kiss, she looked at him and noticed that he had untied his black bowtie and unfastened his top shirt button. It was a sexy casual look that reminded her even more of James Bond.

She slipped her arms from the gown gathered around her waist, and reached up to play with the dangling ends of the tie. "It looks like someone is getting ready for some action," she teased.

He kissed her, again, and then said, "Take it off. Pull my tie off."

She did, and as she dangled it from her fingers, she taunted, "Looks a little like a blindfold, doesn't it?"

"Among other things," he replied. He took her wrists, and as he leaned in to kiss her, again, he moved both of her hands down and around behind her back. He slipped the tie from her fingers, and as he kissed her, he wrapped it around her joined wrists and knotted it.

When he broke the kiss, she asked playfully, "Am I in trouble?"

"That remains to be seen," he answered. He turned her around, and said, "Into the bedroom."

When she got there, she turned to face him and smiled to see that his cock, sticking out through his fly, was still as stiff as when she'd been sucking it.

"Over next to the bed," he told her. "Face it and bend over."

It was a high king-size bed, so when she bent at the waist—with her arms tied behind her— she was able to rest her head on the bed and keep her legs straight. Her belly remained off the bed by a few inches but her bra-constrained tits pressed against the comforter.

He stepped up behind her and lifted the hem of her gown and wadded it up with the top half already around her waist. He then stepped back and admired the sight of her ass covered by the delicate fabric of her red lace panties and framed by the sexy black garter belt and its straps holding up her dark stockings.

He looked in silence for a moment, and then said in pretend anger, "Tell me, Kelly, how many men have had their hands on your ass tonight? Jesus! I take you to a nice party, and you dance with half the other men there and let them fondle your ass! Were you trying to humiliate me? What the hell kind of woman would do that to her date?"

Aside from Carl, several of the older men had given her ass an exploratory feel while they danced. Rather than being offended, it had made her feel sexy as hell!