The Elevator Hook Up

WARNING!! THIS STORY IS NOT FOR EVERYONE!

It contains oral and anal sex between a man and a transsexual. If that in anyone offends you, move on! There are other great stories and authors on this site.

Chapter 1

It was after 11 pm, Allen Crain slid onto the barstool and set his briefcase on the floor. Allen was an attorney for a white shoe law firm on the 60-65 floors of this office building. Although long days were the norm for a litigator like him, working this late was unusual. With the COVID 19 quarantine restrictions, he had the option of working from home. He chose to come into the office after a fight with his wife.

"The usual, Mr. Crain?" Joe, the bartender, was the eponymous owner of Joe's Dinner Club, located on the building's 30th floor.

"Yes, Joe, Thank you! Things must be really slow if you're working tonight."

"Yes, Sir, this COVID 19 thing has darn near put me out of business. What with limited capacity and most of the people who work in the building working from home, business is slow."

"It's the same with my office. But I came in to get away from the wife. You can handle just so much togetherness."

They shared a laugh and a knowing head nod before Joe went to pour Allen's drink. Seven months of forced confinement was exacerbating all of the minor irritations of Allen's 20-year marriage. Their sex life was on the rocks, and they were considering divorce.

The only other customer was a tall willowy blond sitting at the bar. The blond caught Allen staring, smiled, and nodded.

"Here you go, Mr. Crain," Joe said, sitting Allen's drink in front of him.

"Thank you, Joe! Give the beauty over there a cocktail also. Put it on my tab."

"Uh! Yes sir,"

Joe hesitated, thinking he should alert his long time customer that the blond was a regular and a transsexual. Then he figured what the hell. They were his only two customers this evening. Besides, he planned on closing after they left. He prepared the drink and took it to the blond.

"From the gentleman down the bar."

"Thank you, Joe. I've had two already and promised myself I was leaving after this. But I guess one more won't hurt." Heloise Kravet, nee Harold Kravet, took the drink and raised it in a toast to Allen.

"It's none of my business, but you're here late tonight," Allen said, flirting.

"Yes," Heloise sighed, shrugging her shoulders. Her drug and surgically enhanced breasts jiggled as she did. "I have a model agency on the 50^th floor. Most of my models were late because of the damn malfunctioning elevators, so my photoshoots ran late."

"The building manager was in for lunch," Joe chimed in, "he told me he cut his maintenance shifts because of low occupancy. There are fewer guys on days to troubleshoot problems and none overnight."

"It's a sign of the times, Joe! Give the gentleman a drink."

Heloise eyed Allen speculatively. He was middle-aged, grey-haired, and in reasonable shape. He was a little older than her usual hookups but attractive.

As Joe walked over to offer Allen the blond's drink, he rethought his original decision to stay out of the budding relationship between two of his best customers. He again decided to stay out of it.

"The, uh, lady says thanks, and she would like to buy you one."

"Okay! I'm beat, but I guess one more won't hurt." Allen turned on his barstool, smiled broadly, and said, "Thank you!"

"You're welcome! Look, instead of yelling at each other down the bar, why don't you sit with me?"

Allen hesitated, then figured, what the hell. He checked his watch and saw that he had an hour to catch the last train. A drink with a sexy blond would liven up the evening and maybe improve his mood.

Joe watched Allen move and sit next to the blond. He shrugged and decided they were both grownups and would work it out.

"I've never seen you in here before." With a lawyer's practiced eye, he put her in her late thirties to early forties, 5' 7" to 5' 8", 38C, probably 140 pounds. She was a stunner!

"Is that a version of the old pick up line, "Do you come here often? What next? Are you going to ask me about my astrology sign?"

"Do I sound that trite," Allen chuckled?

Heloise considered telling Allen she was transsexual but decided against it. She was leaving after this drink, and a little flirting might brighten her mood.

"Allen, Allen Crain." He offered his hand. "And no, I'm not trying to pick you up," Allen laughed, "you're the one who invited me over. Maybe I should ask your intentions."

"Heloise Kravet," she said, taking his hand, chuckling, "and my intentions are honorable!"

"That's a shame. An old guy like me gets his hopes up when a sexy lady buys him a drink."

"Well, don't get your hopes or anything else up; I was just being sociable. And you're not that old!"

Allen caught the double entendre and decided to ignore it. Heloise was sexy and a great conversationalist. However, he didn't want any entanglements. His personal life had enough challenges.

"At my age, your honor is safe." Allen finished his drink and checked his watch. "Wow! I didn't realize it was that late. I have to catch the last train."

"Thank you for the drink! Could I ask a favor? Could I walk with you to the elevator? We're probably the only ones on this floor, and I'd feel better with some company."

"Certainly," Allen said, standing and pulling Heloise's chair back. "Are you catching the train also?"

"No," Heloise stood, smiling when she caught Allen staring at her legs when her skirt rode up. "I have a condominium on the 70^th floor."

Allen was impressed. Heloise was smart, sexy, and her business must be doing well to afford a condo in this upscale building. He watched the seductive sway of her hips as he followed her to the exit.

"Have a good evening, Joe!"

Chapter 2

Heloise and Allen were standing at the bank of elevators, only one of which was working. Allen felt the effects of fatigue, the drinks, and the captivating presence of this very sexy blond. Impulsively, he embraced her and tried to kiss her.

"Whoa, Cowboy! Where are you going with my waistline?"

"Come on, Heloise! One little kiss won't hurt."

"Allen, we just met, you're married, and we've both had too much to drink! Besides, I'm not THAT kind of girl!"

Allen stumbled back, chastened and embarrassed. He missed the emphasis on the word 'that.'

"You're right! And I'm sorry!"

"Here's the elevator."

Heloise looked at Allen speculatively. He looked interesting, and it might be fun, but he didn't know who she was. That could cause things to get nasty when he found out. She'd been there before and had the emotional scars.

Heloise had a nasty encounter with members of the building cleanup crew who discovered her secret. They forced her into a storage closet and intended to force her to give them blowjobs. They had ripped the top of her dress down, exposing her tits, when the night security heard the commotion and came to investigate, saving her from the unpleasant experience. The building management was outraged, promptly terminated the crew, and pressed charges with the police, but the incident made her leery.

"Shit! It's going down. Do you think you'll be okay waiting for it to come back up?"

"If you promise to behave, I'll ride down with you. That would be better than standing in this hall alone."

"Scouts honor," Allen laughed, raising two fingers in the scout salute.

"Were you a Boy Scout?"

"No," Allen laughed, "but I'll behave anyway!"

Allen ushered her onto the elevator with his hand on her lower back. He pressed the button that would take him to the ground floor where the commuter train terminal was. The doors closed, and the elevator started down. He was about to resume their conversation when the elevator suddenly stopped.

"What the...?" Allen stabbed at the button several times, and nothing happened.

"Shit," Heloise exclaimed, "building maintenance has gone downhill since this virus hit." She pressed the Emergency button and waited for maintenance to respond.

"I don't think that will do any good! Joe, the bartender said they laid off the overnight maintenance crew."

"Ah, yes! I recall that discussion at the last condo owners' meeting. It looks like we're stuck."

Allen dropped his briefcase and pulled out his cell phone. He intended to call his wife to let her know he was stuck in an elevator.

"That won't do any good. There's no cell service in the elevator."

"What the hell are we going to do then?"

"We wait and hope Joe calls someone. He was closing when we left, and this is the only elevator." Heloise sat demurely on the floor, tucking her legs under her. She took off her 5-inch heels and rested her head on the elevator wall.

"You're right!" Allen sat down on the adjacent wall and loosened his tie. "At least the lights are on."

"I don't know, it might be more fun in the dark," Heloise said, playfully leering at Allen.

"I promised to behave! Do tempt me."

"Do you get high? I've got my marijuana vaporizer in my purse. We could toke and relax."

"I haven't in years! My job gives me minimal downtime. Fire it up!"

They passed the vape back and forth, making desultory conversation. The alcohol mixed with the reefer gave them an instant high.

"Are you married, Heloise? Or do you have a significant other?"

Heloise could see where this conversation was going and decided to fess up.

"No, Allen, I'm not married, nor do I currently have a significant other. "I'm trans."

"I'm sorry! You're what?"

"I'm a trans woman." Heloise let the phrase hang in the air while Allen absorbed the significance. She wasn't sure where it would go, but it had to be said.

"So, you're actually a guy dressed as a woman."

"No, that's a crossdresser. I was born a man but never felt comfortable with my assigned sex. I started crossdressing in my teens then took hormones to feminize my body."

Allen took a puff on the vape and handed it back to Heloise. Sober, he might have been taken aback. High, he surveyed her body, marveling at her curves.

"How far are you in your transition?"

"I still have a cock," Heloise chuckled, "I haven't decided to transition totally. Yet!"

Allen unabashedly stared at her, taking in her facial features, her big tits, curvaceous hips, and long shapely legs. He whistled softly. "You could have fooled me!"

"That's exactly what I didn't want to do," Heloise laughed, "We might be stuck here for a while, and I want to be honest with you and not get your hopes up?'

"Get my hopes up?" Allen paused and collected his thoughts. "oh! I see what you mean! I might have thought you were a woman and hit on you."

"Yes, like you did while we were waiting for the elevator," Heloise said, "so I've shared my secret. What about you? Any secrets?"

"Nothing like that," Allen chuckled, "I'm a 50-year-old attorney, married 25 years with two kids in college and a mortgage! No secrets!"

"I'm younger than 50," Heloise said coyly, "Never been married, no kids, but I do have a mortgage!"

"Well, at least we that in common. We both have a mortgage," Allen laughed.

"And one other thing!"

"Ah, yes! We both have a cock!" Allen paused. "Can I ask a personal question?"

"Sure! And look, we're going to be here a while. So let's treat each other like old friends. We can ask or say anything!"

"Okay! Where do you put your dick when you wear a dress like that? I mean, it hugs every curve!"

"I tuck it back between my legs, and my thong holds it in place! Want to see," Heloise asked devilishly, reaching for the hem of her dress?

"No! No," Allen said, laughing and semaphoring with his hands, "I'll take your word for it!"

"I dated an attorney once. He was about your age but married and divorced twice. He said the nature of the job and the long hours you worked put a strain on any relationship. How have you managed to avoid divorce?"

"I don't know. We're going through a rough period now, what with the virus and the quarantine. That was why I decided to come to work in the office today."

"And look at what happened! Instead of being stuck in this elevator with a sexy blond ready to jump your bones, you got me!"

"Don't put yourself down like that! You're hot! Even if you do have a cock. I'll bet you have to fight the guys off."

"Not exactly! But some guys are attracted to trans women. An attorney I was dating said it was my looks, the kinkiness of dating me, and the fact he liked sucking cock."

"Did he and you do anal also? And if I'm getting too personal, say so!"

" Not a problem! We agreed to treat each other like old friends. I was and am hooked on anal even before I began my transition back when I thought I was gay. Back then, I loved sucking cock and getting fucked in my ass. My attorney boyfriend liked for me to fuck him also. It was a match made in anal heaven!"

Allen was taken aback by her honesty. "I've seen anal sex in porn when I surf the web. What I mostly saw was guys doing women. However, there were quite a few with guys doing guys. But it all seemed staged." Allen inhaled the vape and passed it back to Heloise. "My wife and I tried anal years ago. She didn't like it."

"Lubrication," Heloise said, waving the vaporizer, "lost of lube!"

"I'm sorry," Allen asked, "Lube?" the elevator was getting warm, and the heat accentuated the effect of alcohol and reefer. He loosened his tie.

Heloise fumbled in her purse, found the tube of Astroglide, and triumphantly held it up. "Ta Da!"

Allen stared owl-eyed at the lubricant. "Perhaps I should get that for the wife and me."

"She'll love it! But go slow at first. Give her a chance to get used to your cock in her ass. Start with a finger when she is really aroused. Over time fuck her ass with your finger. She'll love that and be anxious for your cock to replace your finger.

" Heloise took a deep drag, held it, then slowly exhaled. "And turn about is fair play. Have you ever experienced a prostate gland massage?"

"Lord, no! I mean, my doctor does a prostate gland exam annually. But nothing more than that."

"Try it; you'll like it! It'll add a little spice to your sex life."

Allen looked at Heloise doubtfully. He doubted if he could convince his wife to let him fuck her ass, let alone give him a prostate massage.

"We had better go easy on this stuff. We don't know how long we'll be here." Heloise inhaled then turned the vaporizer off. A blue haze hung in the elevator. She tried to reach behind her and unzip her dress.

"What are you doing?"

"Don't worry, Heloise snickered, "I'm not getting naked. It's getting warm in here, and I need to loosen my clothes some."

"Turn around! I'll get the zipper for you."

Heloise turned her back to Allen. As she did, her dress rode up until it barely covered her sex. She was aware of Allen staring at her thighs.

"I know this is not a ladylike way to sit, but I'm warm, and it's uncomfortable sitting on this hard ass floor."

Allen pulled the zipper down, revealing her red lacey demi-bra and matching undies. Impulsively he slapped her ass and immediately regretted it. "I am so sorry! I shouldn't have done that!"

"OUCH! That's okay! I like being spanked. But usually, I'm on my knees with a dick in my ass."

Allen's eyes widened, and his mouth gaped open. He stared at Heloise, opened his mouth, then started laughing and couldn't stop. Tears rolled down his cheeks.

"What's so fucking funny?"

"I suddenly had this image of you on your knees with some guy fucking you and spanking you with your cock swinging as he did."

"What's so funny about that? Don't knock if you haven't tried it." Heloise rose to her knees, playfully placing her hands on her hips. The bodice of her dress dropped to her waist, exposing her lacey bra.

Allen stopped laughing and stared boggle-eyed at a perfect set of tits. Heloise looked from him to her breasts.

"Oops! Sorry about that." She pulled her bodice up. "Look, this might be pushing our new friendship, but I have a request. I have a bad back. Sitting against the wall is killing it. Could I sit between your legs and rest my head on your chest. It would help my back."

"I don't know..."

"No funny business! I promise," she lied. Heloise's breast jiggled when she raised her arms to emphasize her point.

"Okay, I guess. Let me take my suit coat off. It IS getting warm in here."

Heloise settled down between Allen's legs and wriggled her ass to settle in, smiling to herself when his hard dick pressed into her butt. She giggled when he awkwardly placed his hands on his legs, palm down, unsure of where to put them. She grabbed them and wrapped them around her waist.

"You'll be more comfortable with them here. But if you squeeze my tits, I'll slap your face!"

"What? I wouldn't...! " Allen stammered and stuttered, trying to defend himself.

"I'm teasing you! But if you want to grab a feel, go right ahead!"

"You are terrible," Allen laughed, "do you treat all your guy friends like that?"

"Most of my guy friends know I'm a tease. Now go on! Squeeze my tits. Satisfy your curiosity."

Allen hesitated, then cupped her breasts and squeezed. He was surprised to hear her moan.

"Are they sensitive?" Allen pushed her bra up and slid his hands up to her nipples. He grabbed them and pulled hard on them. "How's that?"

"You keep that up, and I'm going to make a mess in my panties!"

"Seriously? You can cum from having your tits played with?"

"Yes! They became even more sensitive when I started taking hormones," Heloise said, grinding her behind into his hard cock.

Allen released Heloise's jugs and wrapped his arms around her waist.

"Why did you stop?" She turned in his arms and looked up at him. "Did you remember that a few feet below these tits is a cock and that disgusted you?"

Allen felt the pressure of her hard nipples through his dress shirt. He looked down into her luminous green eyes and resisted the urge to kiss her.

"You don't disgust me. But what we're doing is foreplay. Where would that end up?"

"It could end anywhere we wanted it to end. If I were cisgender and a woman, you'd have me on my back with your cock so deep in my pussy I would gag on it. But I'm a trans woman, and your manhood gets caught up in the taboo of fucking another man in the ass."

Heloise snuggled into his arms. She liked him! He was older than her usual guy, but his intelligence and acceptance of her were compelling.

"Look, this is all new to me. I'm not sure of what I'm supposed to do or say. If that hurts your feelings, I'm sorry!"

He looked at his watch and was surprised to see barely an hour had passed. It seemed longer. In that time, he went from a 50-year-old lawyer contemplating divorce to making out on an elevator with a trans woman. He again caressed her breasts as they talked.

"Mmm! That feels great," Heloise said, grinding her butt into his hard dick and stroking his thigh. "Not bad tits for a trans woman, huh," she said, teasing him and slapping his thigh.

"Not bad, not bad at all. Turn around."

"How do you want me? On my knees or my back," Heloise said, teasing Allen.

"You're impossible!" Allen held her tit in his hand, then took it in his mouth. Her breasts were soft and pliant; her nipples were hard as a rock.

"Oh my God, that feels good! Don't stop!" Heloise's hips pumped as she caressed Allen's head. She managed to ruck the hem of her dress up, pulled out her cock, and started stroking.

Allen was astonished at first, watching her stroke her cock. He watched, intrigued, as Heloise stroke her cock while he caressed one big jug and sucked on the other. In little more than an hour, he went from a Managing Partner in a prestigious law firm to making out with a transgender woman in an elevator. The scene was unreal, something he had never considered in his everyday life.