tagTranssexuals & CrossdressersHelen and Jim Vol. 02

Helen and Jim Vol. 02


The Next Morning

Jim woke up with the sun lancing through his skull. The curtains on his window were open and the sun that normally shone across his feet was shining in his face. That was due to the fact that his feet were enjoying the comfort of his pillow at the moment. Craning his neck he looked at the bedside clock. 7:18 am. Jim let his head flop back onto the bed and the room swam. His stomach swirled in sympathy with his head and Jim assessed the chances of a successful dash to the commode. They weren't very good, so he lay still and in time things settled down. He pulled a corner of the bed cover over his eyes and with it enough darkness for him slip back to sleep.

Hours passed. The sun no longer tormented Jim, but his bladder had decided to pick up where the sun had left off. Stretched to the bursting point it demanded that he drag his abused body to the bathroom for relief. With a Herculean effort Jim levered himself into a sitting position. He waited a moment for things to settle down after changing the direction of gravity on his aching brain. Things calmed more quickly than he had expected and with a small glimmer of hope he stood and made his way across the bedroom to the bathroom. He was intently focused on his goal and only peripherally realized that his clothes, except his under shorts, were folded neatly on a chair.

Jim half collapsed onto the john and sweet relief washed over him as the pressure began to dissipate. The relief was so intense that tears came to his eyes. He put his elbows on his knees as he dropped his head in his hands and released a heavy sigh. He remained in that position for a few minutes until his stomach grumbled. Thankfully it was a grumble of hunger.

Back in the bedroom he pulled on sweat pants and a tee shirt. As his head popped through the shirt he actually noticed that his clothes were folded neatly on the chair. Alarm bells began to go off because he knew damn good and well he couldn't have done that last night. He looked around and didn't see any other evidence that anyone had been in the room. He made his way out of the bedroom and across the living room into the kitchenette. There on his retro 50's diner booth table was a business card. One of his actually, and it was propped up against a Betty Boop pepper shaker. On the back, printed in small neat letters, was the following message:


You owe me pretty big. I don't usually help drunks get home and into bed, but there was something different about you. If you would like to pay your debt, (and I really think you should) call me. 555-8726.


Jim laid the note on the table as bits and pieces of the previous nights exploits began to bubble to the surface of his brain. Was Helen one of the twins or was she some other woman he'd danced with that night. There had been a bunch of them and they had all been friendly. He kept trying to remember the later part of the evening, but wasn't having much luck. There had been two tall women that had sandwiched him for a dance...and during the dance he'd...holy shit! Pulling his waistband out he saw the evidence of how much he'd enjoyed his dance with the women. After all that, and seeing him in his underwear, one of them still wanted to see him tonight? That was very cool, but which one?

Helen had Willie's legs pinned against his chest. A position that Willie generally abhorred, but for whatever reason he seemed to be fine with it now. More than fine actually, he was moaning like he couldn't get enough and that was something that Helen loved. She found it extremely erotic when the guy she was making love to was vocally enthusiastic about it. She dug a good moaner.

"Oh Baby! You're in me so deep! I love how you fill me up so well"

Hearing that made Helen double her efforts and lowering her body onto his she snaked her arms under his so she could grip the tops of his shoulders. She couldn't see his face in that position, but her ear was right beside his mouth and each little grunt and groan sent a shiver through her throbbing penis. She pounded his ass with total abandon as she ramped up to what was going to be a titanic orgasm. His hands were on her ass squeezing and pulling on her, encouraging her to ever greater heights.

"Oh Helen! Ooooooh Helen! Oh my beautiful Helen! I can't take anymore!" Willie liked to call her baby, but Helen was so intently focused on what was going on she didn't even notice he was calling her name. "OH HELEN! I LOVE YOU HONEY!" She felt a sudden warmth spread between their bodies and knew he'd come. Seconds later she joined him and sprayed her own joy deep inside him.

Just as she finished it dawned on her that he'd told her he loved her. She pushed up off of him so she could look in his eyes and said,

"I never thought I'd hear you say..." Her voice trailed off to a stunned silence. Because the eyes looking so adoringly up at her were Jim's.

Helen woke with a start, her face buried in her pillow. She rolled onto her back and sat up. She was alone in her king sized bed and the small slit of sunlight on the floor told her it was late morning. She raised the edge of the cover and peaked down to where she'd just been laying. There she found her come soaking into the bed sheets.

"Great." She said with a sigh. "Now I gotta wash the sheets!"

She couldn't remember the last time she'd had a wet dream. High school maybe? Not that it mattered now because she was the one that did the laundry. No sidelong glances from her mom anymore. Helen flopped back onto her pillow as she replayed the dream through her head. Dreaming about Willie made sense to her. After all she'd been with him for almost a year, but to have dream Willie morph into Jim was something that confused her. She'd only met Jim last night and other than the incident on the dance floor hadn't done anything sexual with him. She had enjoyed undressing him last night and even though she had been sorely tempted she'd refrained from taking his underwear off. He was nicely muscled and she was guilty of letting her hands linger over his body as she undressed him. She had run them over his chest and abs until her panties started to get tight and she became afraid she wouldn't be able to resist the temptation of having him.

As she thought about Jim her hand stole beneath the sheets to grip her half hard penis. She imagined Jim laying beside her with his hand around her cock stroking her as he kissed his way around her nipple. She imagined him squeezing her and making the head of her prick swell, turning it purple. His mouth is now covering her nipple and she can feel his hard on pressing into her thigh. He's flicking her nipple with his tongue as he humps her thigh, rubbing his excitement against her gets her even more excited. Her hips meet the thrust of his hand as he strokes her from tip to base, the pre-come dribbling down to add its lubrication to the swelling enthusiasm. Helen is breathing hard, swept away by the pleasure Jim is giving her.

When the phone rings on her night stand Helen almost jumps out of the bed as the fantasy about Jim implodes. Her cock is tingling with excitement, but the mood is broken. She lies there as the phone rings a couple of more times and finally picks up just before it goes to voice mail.


"Has he called yet?"

"No Angel." A long pause.

"Did you do him last night?"


"Ok, Ok...don't' get so defensive. You were gone awhile so I thought that as horny as you were you might have...you know...slipped him a little something to remember you by."

"In the shape he was in I doubt if he could have remembered anything anyway. All he would have known was that his butt hurt."

Angel let out with an evil snicker on the other end of the phone and said,

"Helen sweetie, I'd bet money that if you'd have done him, he would have remembered it. You're not the kind of girl the boys forget!"

"Well I didn't do him and if he doesn't call I won't get the chance. Do you think he remembers us rubbing our hard-ons against him?"

"Who knows? Give him some time to call and that may tell you. I know one thing for sure; he was really getting into that whole scene of us 'doing' him on the dance floor. He's got some great potential as a lover if he's not too uptight to be with a girl like you. Or me for that matter!"


"Alright, alright! I'll leave him alone. Geesh, you act like I'm some horny girl that's got to have every cute guy sees!"

There is only silence on the other end of the phone.

"Oh whatever Helen! Let me know if he calls you."

"I will. Talk to you later Angel."


Angel hung up and Helen rolled out of bed. She padded into the bathroom on bare feet and stood over the toilet bowl to pee. There were lots of mirrors in her bathroom and she could see herself from behind. She thought she looked pretty good with long legs flowing up to make a nice round ass (all hers!) and dark hair hanging down to just above the light tan line that announced where her bikini strings cut across her back. She had full hips and just enough fat to give her a soft curvaceous figure. She liked what she saw and thought that she looked like any other woman other than the fact that she was standing there pissing in the toilet. She shook the last drops into the toilet and then pulled on some panties, jean shorts and baggy tee shirt to work in around the house. The only sign that she wasn't like every other woman cleaning house that Saturday was the prominent bulge in her jean shorts.

Jim was doing the dishes from his early afternoon breakfast. A couple of slices of whole wheat toast and two eggs over easy fried in just a bit of butter seemed to have stopped the grumbling of his gut without causing it to reject the peace offering. Try as he might he couldn't seem to peer through the fog that obscured what had happened last night. The last thing he could remember was being sandwiched between those two beautiful women and them holding him up and grinding their crotches against him until he came. In his head it was as if he'd been the girl and they'd been dry humping him, but that couldn't have been what happened. Could it?

He gave up trying to remember and slid his feet into an old tattered pair of dock shoes and went down the inside stairs to his garage/workshop. He looked at his car projects and decided that he was way too hung over to deal with tools, loud or quiet ones. He needed to run over to the west side of town to pick up some swap meet parts he'd bought and decided that he was more likely to survive a soothing drive than anything else. He went back up stairs to get some shorts and the keys to his truck. Thank goodness he'd at least had the good sense to take a cab to the club last night!

Jim changed his clothes and grabbed his keys. He was just about ready to head down to his truck when he noticed Helen's note again. He stood and looked at it for a moment. He liked the name Helen. It had a retro sound to it and that was when it clicked that Helen was the brunette bombshell that he'd faced when she and the blonde sandwiched him. He picked up the card and stuffed it in his pocket with his cell phone.

Later That Day

Both Helen and Jim got some of their work done while they dreamed and wondered about each other, but their fantasies were way off the mark. Jim Imagined Helen moaning in ecstasy as she sat on the front tire of his street rod and he pleasured her with his tongue. Helen imagined Jim grinding his big (but not bigger than hers) hard on against her thigh in eager sexual agony as they made out.

Jim had opened his phone several times and even put Helen's number in once, but so far he hadn't hit the send button. Throughout the day Helen would pass her phone and each time she found herself willing it to ring. She didn't know why, but Jim had really gotten to her. Finally the phone rang, but since she was running the sweeper she didn't hear it. As soon as she saw the message light blinking she pounced on the phone. Her heart hammering in her chest as the mechanical voice muddled through its directions. As soon as she heard the voice her heart dropped into her stomach.

"Helen where are you? Has your Prince Charming called and whisked you away for the evening? If not, why don't we go out again tonight? Give me a call and I'll pick you up around 9. Later babes!"

Angel. Helen sighed as she realized that she should just stop hoping for Jim to call. Maybe he remembered last night too well. Maybe he remembered the two hard girl cocks that had brought him to orgasm on the dance floor. Yep, that might do it.

Across town Jim was sitting in the parking lot of a burger joint that had opened for business about the same time Jack Kennedy was taking up residence in the oval office. He was alone in the cab of his Dad's '68 Dodge pickup in the shade of the Drive In awning. A hot dry breeze was blowing through the cab and making the ice in his sweet tea melt all the faster. In one hand he held a deliciously greasy double bacon cheese burger that was guaranteed to erase his hangover. In the other was his phone with Helen's number already typed in and his thumb was hovering over the SEND button. He pushed SEND and after a few seconds it started to ring.


"Hi. Is Helen there?"

"This is Helen."

"Hi Helen. This is Jim, and I think I owe you both an apology and a thank you. I don't usually drink like that, but I've been out of the dating scene for a while and I guess that I was relying too heavily on liquid courage. So for the apology part, I'm sorry for being a burdensome drunk."

Helen laughed and he continued.

"Now for the thank you part...will you please allow me to take you out this evening?"

"After such a sincere apology how could I refuse?" Jim could hear her smiling through the phone and that made him smile too.

"One last thing. Are you willing to ride topless in a car?"

"Isn't that a little forward for the first date? I usually don't take my top off till at least the second date!"

"NO, NO! I meant the car! Not you!"

Helen laughed out loud and Jim thought he now understood the line in that Cake song Short Skirt, Long Jacket about her voice being dark like tinted glass.

"I know. But if you set them up that easy you have to expect me to knock them out of the park!"

Jim let out with an overly animated groan.

"Let me explain. I have an old car, a hot rod if you like, that does not have a roof. I was wondering if you would be willing to ride in it with me to a cruise-in down by the board walk. We'll get something to eat while we wander around amongst the other cars and then who knows? Whatever we think of next."

"Is your car a Rat Rod?"

"Well, I don't call it that, but some folks may think that's what it is. It has flat black paint and skinny tires. I consider it a traditional rod, but what's in a name. It's a cool old car to me and I like it."

"Is this cruise-in one where people dress like back in the 50's?" Was that interest he heard in her voice?

"Some do, but it's not required or anything, you can pretty much wear whatever you want."

"Oh. Would you mind if I dressed like that?"

"Hell no! That would be great! How about I pick you up at 6?"

"It's a date!"

Helen gave Jim directions to her house which he wisely wrote down in a note book he kept in the glove box. When they hung up both of them were grinning like the cat that ate the canary.

First Date

Jim pulled up in front of Helen's house at precisely 6 pm. He left the car running as he went up the front walk and just as he was getting ready to ring the bell the door opened. There standing before him was a beautiful 1950's pinup girl. Jim hadn't really known what to expect, but this was far more than he could have hoped for. Helen's dark hair cascaded down onto her bare shoulders where a red and white striped halter top held an impressive bust line. A white pair of Capri pants and some wedge heel sandals rounded out her outfit. Jim could only stare at her with his mouth open. Helen laughed and said,

"That's the same look you gave me last night at the club!" She reached out with a soft hand and once again closed his mouth.

"You look incredible! Why if I didn't know better I swear that you're Betty Paige's little sister!"

Helen smiled at him and his soul brightened.

"Awww, thank you Jim! That's so sweet of you! She's one of my inspirations."

She looked past Jim to where his car was crouched by the curb. Now it was her turn to be impressed.

"Wow, a '32 Ford roadster. Very sweet!" She walked slowly toward the car drinking it in. The early evening sun glinted off of the few chrome pieces and the rest was all flat black, except the wheels which were bright red wire spokes. The engine compartment didn't have a hood and the engine right there for the world to see. "What? No flat head V8? The Ford guys must give you a lot of crap about not having a Ford engine in it."

"You seem to know quite a bit about cars! You even got the year right. I've never had a woman that could tell me what year this car is actually ride in it. And to top it off you're asking me why it doesn't have a flat head! I can't believe this!"

"Oh don't take it too hard. I don't mind the fact that you're running an old Hemi. I think that it's a nice twist and back then there were quite a few guys that put different engines in their '32s."

"You know that's a Hemi?"

"Well yea. There're easy to spot with the plug wires disappearing into those wide valve covers."

Without another word Helen hopped over the door and settled into one of the bomber seats. She looked at Jim who was still standing beside the car with an awed expression on his face.

"Are we going?"

"Oh yea baby! We're going alright!"

Jim hustled around the car and hopped in beside the beautiful pinup girl. Helen put on her big dark sunglasses and said.

"Show me what she can do."

Needing no further encouragement Jim dropped the hammer on the ole girl and did a burn out away from the curb that would have made any high school kid proud and one red M3 convertible green in envy. Helen let out with a, "Wooohooo!" as they shot off down the street.

They didn't talk much on the way to the cruise-in, they just kept stealing glances at each other. Jim couldn't believe how beautiful this woman was and to top it off just how perfect she looked in his car. Helen thought that Jim was looking pretty darn fine too. He had on a pair of peg leg blue jeans and a simple white tee shirt that fit snug along his body. He was built nicely, muscular but not overtly so. He looked strong and lean. She especially enjoyed watching his hands on the wheel and shifter. She imagined how they would feel on her body. Caressing down along her sides and onto her hips, then around in front to grip her growing girl cock...this began to make her pants tighten so she turned and watched the world go by as she took a few deep breaths.

Jim wanted to have the normal fantasies about Helen, but every time he got to the part where she saw his penis the fantasy came crashing to a halt. He shook his head to clear it and concentrated on driving the car.

They rolled into the cruse area going nice in slow. The big Hemi announced to the crowd that not only had they arrived, but they were ready and willing to take on anyone who wanted to go head to head in a quick street race. Jim saw his usual group of guys parked at one end and guided his roadster to join them. He tried to ignore how his buddies were nudging each other and nodding his way when they noticed Helen in the car.

Once he got parked he put a hand on her leg and said,

"Let me get the door."

Helen had also spied the guys nudging each other and understood that Jim wanted to put on a show for them. He hopped out of the car and hurried around to her door. Opening it with a flourish, he took her hand and helped her out of the car. Every eye turned to watch this tall beautiful woman unfold from Jim's car. Helen looked more like a movie star arriving on the red carpet than a pinup girl at a cruse-in. Jim offered Helen his arm and with a huge smile she took it and leaned in against him as they started off down the line of cars.

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byruwild© 19 comments/ 66169 views/ 58 favorites

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