An Unconventional Convention

"There's a cabinet in my shop in the basement that I keep locked," he replied. "She never goes down there, anyway. She's terrified of spiders."

They reached the pub, and Casey said, "So, do you have another name you like to go by when you're dressed up and out in public?"

"Kelly," he answered.

"Well, it's a pleasure to meet you, Kelly," Casey said as he extended his arm for her to take. "What do you say we leave your boring friend Rich out here in the mall while you and I go in and get to know each other better?"

Rich smiled--still amazed at how easy it was to be so open and honest with this stranger--and said in his Kelly voice, "Thank you. I think I would enjoy that very much. And I'm sure that Rich will be all right by himself for a while. If he gets lonely, he knows the way home; he can call an Uber."

Kelly took Casey's arm and they walked into the pub.

They took seats at the bar, and when the bartender came over, Casey said, "A gin and tonic for me, and the lady will have..." He looked at Kelly as he thoughtfully rubbed his chin, and then went on, "I'm guessing either Chardonnay or a sidecar martini."

Kelly smiled and said, "Chardonnay is my go-to, but I'm feeling like I should step outside my comfort zone tonight." She turned to the bartender, and told him, "Sidecar martini, please." She turned back to Casey, and added, "I've never had a sidecar; thank you for the suggestion."

"So, tell me a little about yourself, Kelly," Casey said as he turned toward her on the swiveling stool and put one arm up on the bar. "Married? Kids? You live here in Springfield?"

"Divorced," Kelly replied. "One daughter. She'll graduate high school in June. I'm so proud of her." Kelly had often thought about her alternate life when she was dressed up, but until now, it had all resided in her head. Talking about it was unbelievably freeing!

"Really?" Casey said. "When the heck did you have her? You don't look old enough to have a high school freshman, let alone a senior."

Kelly smiled, and said, "Thank you. I was pretty young; just a senior myself. She was conceived on prom night on a blanket under the stars."

"Romantic," Casey commented.

"Horny," Kelly replied. "It was the first time I'd ever gone all the way with a boy." She chuckled, and added, "I should have stuck to my original plan of just a blowjob."

"Does she take after you?" Casey asked.

"You mean is she horny and dumb enough to get herself knocked up?" Kelly replied.

Casey laughed and said, "I actually meant is she as attractive as you. Which, I guess, could lead to what you said."

"She's a little more curvy than me," Kelly answered. "A little wider hips and a bigger bust. Same round ass. But she's smarter, too. When she decided she wanted to become sexually active, she came to me and we got her on the pill. Like I said, I'm pretty proud of her."

"Is her father still involved in her life? Your life?" Casey asked as the drinks showed up.

"No. We divorced after just a few years," Kelly said. "He actually went on to become a doctor, but he couldn't keep his dick in his pants. By the time we split up, he had fathered two more kids--both to married women. Aside from the child-support checks--which have ended, now--and Christmas and birthday gifts he wasn't involved at all."

Casey lifted his gin and tonic, and when Kelly had picked up her martini, he said, "Well, here's to you, Kelly, for raising a daughter who can make you proud all on your own. The world needs more strong intelligent women like you, and apparently, her. Cheers!"

"Thank you," Kelly said as she clinked glasses. She took a sip, and said, "Oh, that's nice! I may have a new favorite. Or at least a new back-up."

"I'm glad I didn't lead you astray," Casey said. "I'm not sure I could finish both of these if you decided you needed to go back to Chardonnay."

"Not at all," Kelly said. "Thank you for the suggestion."

"So, what do you do for a living, Kelly?" Casey asked.

For the next half hour they shared pleasant conversation, mostly about her, but she asked about his life, as well.

Talking to Casey made her imagined life seem somehow more real, and the fact that he was playing along--allowing her to be Kelly--took it to a level he had never even hoped for.

Wearing women's underwear had always made Rich feel free of the male shackles that he felt society put on him. When he donned his first dress it only enhanced that feeling. The first time he dressed up with a wig and full makeup, and went out in public, he thought he had reached the zenith of what crossdressing could possible deliver. The glue-on breasts did take that a step further, but none of it prepared him for the feeling of being talked to, treated like, and appreciated as a woman. And far more than normal when just crossdressing and walking around in public, he felt aroused.

"I have to tell you, Casey," Kelly said, "that you make me feel more like a woman than I've ever felt before. And I deeply appreciate that. But it also makes me kind of want to act more like a woman than I ever have, too." She looked Casey in the eyes, and went on, "I swear I have never said this to anyone before in my life--and just say no if you're not interested--but I would really like to go back to my room with you and give you a blowjob. I would like to feel your hard cock in my mouth, and I'd like to suck the cum right out of your balls and swallow every one of your wiggling little sperm."

Casey looked at her for a moment, and then said, "Well, I guess I should have seen that coming."

Kelly wasn't quite sure how to take that, but she said, "If I've offended you, Casey, I apologize. It's just that you've taken me to a whole new level with the way you treated me and talked to me. As well as actually wanting to do it, I thought maybe I could give you something appropriate in return for making me feel so much like a woman."

"Yeah, again, I should have seen that coming," Casey said with a little sigh. "The see-through blouse, the half-naked tits being held up on display by the black bra, the ass-hugging skirt. I should have known you were a slut!" He let that hang for just a moment before adding with a smile, "I like that in a woman!" He waved at the bartender, and said, "Check, please!"

Kelly gave a relieved laughed, and said, "I hope you have as big a prick as you are one."

"I'm looking forward to you being the judge," Casey said as he put his credit card on the bill. "Shall I call a ride-share?"

"I have a rental car," Kelly said.

As Kelly drove, she said, "So, um, you want to go into the hotel separately? Just in case there's some other artist in the lobby who recognizes ears."

Casey gave a dismissive, "Phfft!" and added, "They'll all be looking at your tits, anyway. No, we'll go in right through the front door, arm in arm, they way a lady should be escorted."

Kelly smiled as she drove, and said, "Thank you. You're making this whole thing pretty damned special for me. I hope I'm able to adequately show my appreciation." She looked at him for a moment, and asked, "Is this, um, your first time, you know, going this way?"

"If you mean have I ever sexually batted from the other side of the plate, yes," Casey answered. "A long time ago, in high school, a buddy and I did some sexual exploration. We started off jerking off together to looking at dirty magazines, then jerked each other off, and eventually graduated to giving each other blowjobs. He moved away the summer after graduation, and I moved on to girls, and my switch-hitting has just kind of set on the shelf ever since. But I'd be lying if a said I haven't thought about it over the years."

"Well, I wasn't lying before when I told you this was my first time taking things this far," Kelly said as she turned into the parking garage. "I'm so nervous and excited that I feel like a freaking virgin!"

Casey laughed. "Maybe like your mom did on prom night," he said. "Relax. The consequences can't possibly turn out the same."

Walking through the lobby on Casey's arm, Kelly held her head high, and her shoulders squared. After getting out of the car, she had re-tucked her blouse, so the light fabric was now prominently tented by her stiff nipples. Catching glance in her peripheral vision, she wore a wide grin. She had never felt so pretty and sexy in her life.

As the elevator arrived at the lobby, they heard, "Hey, Casey!" called out by a male voice from behind. "Hold the elevator!"

They turned to find a handsome bearded man hurrying toward them.

"Oh, hi, Ken," Casey said as he allowed Kelly to step into the car first, and then held the door with his hand. As the door closed, he made introductions. "Kelly, this is Ken. We used to work together, but he moved off to Arizona for the dry heat. Ken, this is my friend Kelly."

"Pleased to meet you," Ken said. "Are you here for the graphics convention, too?"

"No. I'm in town visiting family," she replied. "Casey and I know each other from our college days. We happened to run into each other at the mall."

After Ken got out on his floor and the doors closed, Casey laughed, and said, "See, I told you not to worry. Did you catch him checking out your tits? I'm sure he thinks that you're a hooker that I'm taking back to my room."

She laughed, too, and said, "I'm torn between being insulted by that and feeling off-the-charts sexy because of it."

"Take the sexy," Casey said, "You earned it."

At her room, Kelly handed Casey her room-card so he could open the door for her. "You'll have to excuse the mess," she said as he pushed the door open, "I certainly wasn't expecting company when I left earlier."

The room was bigger than Casey's; sort of a mini-suite. He wondered if that was a perk that speakers at the convention got.

Casey sat on the edge of one of the two queen-size beds as Kelly put Rich's pants and shirts back into the suitcase to neaten the place up. "Oh, hey, how about some music?" she asked when she noticed the light blinking on the Bluetooth speaker on the dresser.

"Sure," Casey said, amused at how nervous Kelly seemed. It was like she was a virgin. "Would you like something from the mini-bar?" he asked her.

"Oh! Yeah, that would be nice," Kelly said as she opened her music app and restarted her smooth jazz playlist. "I think I'll have that Chardonnay, now, please."

As Kelly put her makeup into her kit, Casey found a couple of wine glasses in the kitchenette and poured the single-serving bottles of wine. Chardonnay for her and cab for himself.

He got her to stop primping the place and handed her her glass. "If you're having second thoughts about your offer to show your appreciation, Kelly, I'm okay with that," Casey said. "I've already enjoyed the unique circumstances of this evening more than I could ever have guessed I might." He raised his glass, and added, "Here's to unexpected meetings."

Kelly smiled as her nervousness waned a little, and clinked his glass. "Thank you. And here's to new experiences." They each took a sip, and she added, "No second thoughts. I may never get this chance again. Maybe a little performance anxiety, though. This is my first time going this far down the road."

"Relax. You'll be great," Casey said and they each took slightly longer sips of their wine. "It's not like I have much experience here, either, and what I do have is a long way in the rear-view mirror."

Kelly wasn't sure what Casey meant by that. Was he prepared to return the favor? Kelly wasn't sure she wanted that. Getting oral sex from him would stick a pin in the whole make-believe bubble that she was enjoying so much.

As they sipped the wine, The Nearness of You, by Rod Stewart, began playing over the speaker. "Would you care to dance?" Casey asked.

Kelly smiled, and said, "Oddly, in all of my imaginings, I've never thought about that. Yes, I think I'd like that very much."

They set their glasses down, and Casey took her in his arms. She put hers around his neck, and snuggled her body against his. He was just under six feet tall, and she was five-eight in her pumps, so she had to look up at him just slightly. She enjoyed the pressure of their embrace through her breasts, but also felt a little disappointment that she couldn't feel his chest against her hard nipples as they moved.

As they swayed gently to the music, Casey began to sing along softly; a habit that he had while dancing with anyone. "... It's not your sweet conversation that brings this sensation; oh no, it's just the nearness of you..."

Contented in a way that she had never experienced while dancing before, Kelly laid her head on Casey's shoulder and lost herself in the moment.

When Casey and Rod both sang the final lines of the song, "... to hold you ever so tight, and to feel in the night, the nearness of you..." she raised her head, looked him in the eyes, and said, "Will you kiss me?"

"Your first kiss?" he replied with a small smile.

"Kelly's, yes," she answered.

"Well, I'm honored," Casey said and leaned down. He pressed his lips to hers, and for several seconds they moved their mouths against one another while gently rocking their heads. It had all the makings of a warm, passionate kiss, but when their lips parted, Kelly looked up at him with a slightly quizzical look. "Curious," she said. "I had expected to enjoy that a lot more, because I certainly have enjoyed every other new thing tonight. It was a wonderful kiss--and thank you--but it really didn't do anything for me, if you know what I mean."

"Yeah, I can't say that I got much from it either," Casey said. "And I had wondered if I would. My buddy and I had tried kissing back in the day, with pretty much the same result. Maybe it takes two different kinds of spit to get anything percolating."

Kelly gave a small chuckle, and said, "Maybe. But now I'm nervous that I won't be able to get you percolating at all, and this whole wonderful evening that you've given me will crash and burn for both of us."

Casey smiled, and said, "Oh, I have complete faith in you!" He took one of her hands from his neck and guided it to the front of his pants. "See?" he went on. "You've had me percolating since you first told me your name, Kelly."

She rubbed his pants gently, easily feeling the outline of his cock. She could feel enough flexibility that she knew he wasn't fully erect, but just that touch renewed her confidence and injected a shot of arousal through her own body.

She smiled up at him, and maintaining eye contact, she slowly lowered herself to her knees on the carpet. She unbuckled his belt and then slid his zipper down. She eased his pants off of his hips, and lowered them to the floor. Looking up, again, she said, "Do you want to take them off? No sense letting them get all wrinkled."

Steadying himself with a hand on her shoulder, Casey pried off his shoes and then lifted one foot at a time letting Kelly get his pants off. She laid them out on the floor beside her, and folded them into thirds.

She turned back, smiled up at him, again, and then dropped her gaze to his black boxer shorts. She ran her fingers gently over the bulge of his cock, and felt it move under her caress. His reaction to just her light touch renewed her confidence and made her smile. It also doubled her own arousal.

She slid her hand into the fly of his shorts, and wrapped her fingers lightly around his dick. It was a first for her, and she smiled broadly at the feeling of the smooth, warm skin, and its twitching reaction to her touch.

Knowing that she probably would not have long before Casey's inflated penis became a full-fledged boner, she gently pulled and maneuvered his still-flexible member out through his fly while she still could.

Gently holding his quickly-stiffening cock in one hand, she reached in through his fly with the other and delicately extracted his balls. She then let go of him with both hands and looked at the boner just inches in front of her face as it bobbed slightly in time to Casey's heartbeat. The contrast of the pinkish-flesh tone of his cock and balls against his black shorts, almost as if it was sticking out through a glory-hole, was surprisingly arousing--for both of them--all by itself.

Looking down at his protruding dick, Casey took his shirttails and tucked them up inside his shirt so they wouldn't be in Kelly's way... or in his way of the view.

Kelly put both of her hands back on Casey's now-fully-erect cock and ran her fingers up and back feeling the warmth of the taught, smooth skin stretched over his blood-inflated muscle. She explored its shape, narrowest at the base, increasing in diameter a little beyond the middle to where her finger and thumb would barely touch around it, and narrowing back down just behind the pronounced ridge of his cock-head.

She slid her finger tips back along its length, tracing the twisting bulges of the engorged veins, and then forward, again, drawing both thumbs along the contrastingly-supple urethra that extended the length of the underside of his otherwise rock-hard cock.

Once again reaching Casey's cock-head, Kelly stopped as her fingers came against its fire-helmet ridge and simply held his erection in front of her face. Its tip glistened with Casey's pre-cum, and its shimmer gave Kelly another jolt of arousal knowing that she was responsible for that. She desperately wanted to stick out her tongue and taste the clear fluid, but she managed to resist the urge... for now.

She extended one thumb onto the sensitive triangle of skin that formed the underside of his cock-head and gently caressed the spot. When she did, Casey let out a low moan, his whole cock throbbed, and a fresh droplet of per-cum oozed from the tip. At that point, Kelly lost the battle with her self-control.

Before the new pearl of dick-juice could drop off onto the floor, Kelly extended her tongue, leaned in, and ran it from her thumb up across Casey's pee-slit, catching the escaping drop just in time. She then pursed her lips and placed a gentle, sucking kiss against his cock-head.

Holding the kiss, she extended the tip of her tongue between her lips and his knob, replacing her thumb at the little underside patch. She then slid her hand back along the length of his cock, and when she drew it forward, again, she increased the pressure on her thumb causing a milking action along his urethra.

As her hand moved forward, she sucked a long stream of warm, salty pre-cum into her mouth--easily more than she had ever tasted if she combined the many times she had scooped a glistening droplet from a cock-head with her fingers and transferred it to her mouth.

She savored the taste for just a moment before sucking Casey's entire cock-head into her mouth and closing her lips tightly around its thick ridge. Held captive, she ran her tongue all over its surface, through its underside-cleft, up through it's pee-slit, and even as deep into Casey's pee-hole as she could wiggle the tiny tip.

While she sucked and tongued his knob, thoroughly enjoying that new experience, she stroked his still-dry cock with a circle made by her thumb and finger applying only very light pressure. Casey let out a low, "Oh, Lord!" and Kelly had to fight to keep from breaking into a wide smile and losing the suction she had on his cock-head.

With every square millimeter of his knob thoroughly explored with her tongue, she leaned forward, and with her lips still tightly fixed around his stiff cock, she slowly took as much of it into her mouth as she could.

She felt her lips expand over its thickest part and felt his squishy, fat knob press against the roof of her mouth while she rubbed her tongue along its underside.