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Chapter 57
by grimbous
What's next?
The Date Finale
You turn on the wipers and cruise the highway back home again. No singing this time, both of you now just sitting quietly and watching the road flow by. The slap of the wipers and the rapping of rain filling the dark silence. This night sure as hell didn't go the way you had hoped it would.
The rain gets harder and harder as you go. The pitter pat on the drops drum down on the soft top of the Queen. The tension was unbearable.
You clear your throat. "So...uh...how does it work? If you don't mind me asking."
"Work?" Casey's honey sweet voice asks from the darkness.
"Yeah. Like...are you trans or like...I dunno. Why do dress like that?" You shift uncomfortably, this was awkward but your curiosity was getting the better of you.
"Do I really need a label?"
"Uh...no, I guess not. Just...it's different ya know."
"I know. My parents are what you might call free spirits Jesse. All of their friends theater people, most quite eccentric. We moved a lot. I was home schooled and tutored when I was younger, not many other kids around. I grew up just...being able to express myself. However I wanted, whenever I wanted. It was never a big deal. Until high school anyways." She goes quiet, there were unspoken volumes in that pause you were sure. She finally says. "That's when it really hit me that I was different. It hit me hard if I'm honest. If it wasn't for Felix...well..." He sighs. "...let's just say it wasn't easy."
"I bet." You say.
"I eventually found it better to just settle into one thing. It was easier for people to deal with. People don't like uncertainty and blurry boundaries. I embraced my femininity and haven't looked back. I like softness and compassion and gentleness. I don't think there is anything wrong with that. I like beautiful things Jesse. I like to feel beautiful. I want to be beautiful." Her voice was quiet, but there was a strength to the words. Casey knew who she was and she wasn't ashamed of it.
A distant flash of lightning illuminates Casey's fine boned face for an instant.
"You are...beautiful." You admit. It was the truth.
"For a guy?"
You nod. "Yeah. And...ya know...just in general."
"Well...thank you."
Drip.
You feel something hit your hair.
Drip. Drip.
Reaching up you run you run your hand over your well groomed head to feel a spot of wetness.
Drip. Drip. Drip.
"Your roof has a leak!" Casey says. "Oh geez, right over the driver's seat."
Drip. Drip. Drip. Drip.
"Fuck." You grumble. "Par for the course for this night."
You hear Casey unbuckle and slide across the the big bench seat toward you. Reaching up she places a hand over the small leak above your head. You stiffen in spot, tensing up uncomfortably. Casey was right up beside you. His arm just behind your head. His chest against your shoulder. You could feel the heat of his body, the moisture of his breath, the intoxicating aroma of his perfume.
He was looking around for something to staunch the drip. Your car being new however you had nothing in here yet. Also, it being so dark it was hard to see anything. You drive for a time, your eyes locked straight ahead. The rain was escalating fast, now coming down in sheets. You remember how nice it had felt having Casey on your arm. Holding her soft hand. You remember the otherworldly sound of her crystal clear voice.
"Hmmm." Casey says. "Maybe we can patch this or something. I have a little sewing kit in my purse." His arm was tiring, forcing him to shift a bit closer to you. His hip presses into yours, his chest pushing even tighter into you. He is looking up. "I think it's just a small hole. Pull over, let's see what we can do with it."
You nod. Thankfully the highway had wide shoulders along this stretch. You pull the Queen off to the side and slowly bring her to a stop. You put her in park.
You turn to look at Casey just as another flash of lightning illuminates her face once more. Wide green expressive eyes, perfect ruby lips, an elegant nose, flowing natural hair. Even up close, only a few short inches away, she was simply one of the most beautiful women you had ever seen...
He shifts his eyes from the leak down to meet your gaze in the ultra dim light. "In my purse there's a...there's...a..." Her voice fades as she sees how you were looking at her. "Jesse?"
In one swift motion your hands come up to cradle her face, your palms just below her jaw, your fingers curling in behind her ears, your wrists against her soft slender neck. Her hair like strands fine silk over the outsides of your hands. Twisting in your seat you pull her to you and you kiss the luscious red lips you had been dreaming of since that night in the diner. They were even better than you had imagined.
You kiss her tenderly but with passion. Your partially open mouth pressing softly into hers.
"Mmmmm." She hums softly as she melts in your hands. Her arms come down, her delicate hands resting lightly on your shoulders.
Drip. Drip. Drip. Drip. Drip.
The leak patting down on your head once more. You didn't care, you barely felt it. You slide your arms around her and pull her to you, holding her tight as your kiss goes on and on.
You had told El once that if you hadn't been her brother, and if you had been interested in her, that her unique condition wouldn't matter to you. You told her that the heart had a way of ignoring the unimportant stuff and letting you see the truth. You liked Casey...you really liked Casey. She was kind, she was classy, she was talented. She was a lady through and through. She was all woman as far as you were concerned. So she had the same equipment as you...who cares?
Some part of you admits that thinking about your family in certain forbidden ways since the big reveal had surely weakened your resistance to certain things. If so, it just meant that this was meant to be. Your path had lead you here for a reason.
Reaching down you unfasten your seat belt then take Casey back in your embrace, your lips never leave her. You push her back toward her side to get out of the dripping rain water.
"Mmmmmm." You let out a low growl into her mouth.
"Mmmmm!" She responds in a light voice.
Her hands gripped your silk covered chest as yours stroked across her back. You kiss her deeper and harder. To your enflamed senses she tasted so much better than any woman you'd kissed before. Her womanly aroma fills your nostrils sending you to new heights. The tips of your tongues meet and begin to flick and dance together.
You wanted to go further, you wanted to go all the way, but not tonight. You knew it wouldn't be tonight. Casey was an old fashioned lady and you respected that. Besides...you had a wager to worry about. It may have only been first base but for now it was enough!
Your hunger and anticipation would stay at a fever pitch until...hopefully...a next time.
In the front seat of your old Cadillac Eldorado on the side of the rain soaked highway you and your Irish rose Casey Devlin make out for a long and wonderful time. Kissing, feeling, caressing, pressing your clothed bodies together. You kiss her lips and her cheeks and down her long neck. She runs her hands through your hair and lets out sighs of pleasure. Cars pass by and thunder rolls through the sky. Lightning flashes and rain drums on your roof. You notice none of it. For now the whole world consisted of you and this fire haired angel.
You finally part, both of you breathing heavy. "Ohhhh Jesse." Casey moans softly.
You run a hand through her hair and kiss her yet again. And again. And again. Her kisses like the most addictive of ****. This starts a new round of making out. You didn't want to let go of her, not even for second.
Just then your phone rings. You ignore it.
After it finally stops...it starts ringing again. You glance at it in annoyance. You wanted to launch that phone out onto the rainy highway. You try to stay focused.
Again it rings!
"You should get that." Casey whispers, her fingers trace down your stomach. "Might be important."
You let out an irked sigh. "Yeah."
You fish it out and look at the screen. It was your mother. You consider ignoring it but your mother knew about your big date tonight and what it meant to you, she wouldn't call unless it was important. You answer. "Mom? This really is not a good time."
You hear loud music and strange noises in the background. Your mother's frightened voice responds. "Jesse? Jesse...sorry...it's Fiona. She's out of control." You hear something crash and your mother screams at your sister. "FIONA! STOP IT!" She returns to you. "I...I didn't know who else to call...she won't listen to me. She's been drinking and she's acting crazy and she's got these weird friends of hers over. I don't want them here." Your mother sobs. "I don't want to call the police. I...I didn't know who else to call. Could you come talk to her Jesse? Maybe she'll listen to you."
In an instant the mood of the magical moment was spoiled. Fucking Fiona!
You sit there wondering what you could say. You wanted your mother to treat you like an adult...well, she just started. Time to step up. You straighten up. "Mom, go over to Peggy's for the night. I'll be home as soon as I can."
"Okay Honey." She says, her voice at a sudden whisper. "Thank you. Please hurry."
You hear raucous laughter then your sister's slurred voice. "Who's that you talkin to Ma!? Invite em over!" More laughter follows.
"I love you." Your mother says to you hastily.
"Love you too Mom."
She hangs up.
You slump down in your seat. "Fuck."
"Trouble at home?" Casey asks.
"Yeah...my sister."
"Not Elsie?"
You shake your head. "No, my big sister Fiona. If there's drama in my family Fiona's in the middle of it. Fuck!" You look over to her. "Sorry, I gotta go home. I'll drop you off."
She strokes your shoulder. "Sure Jesse. I understand."
She understood? You didn't even understand.
"Jesse?" Her hands were now folded on her lap, her head down and her eyes glancing toward you in short unsure looks.
"Yeah?"
"This...this wasn't just a one time thing, was it? A moment of madness? A...um...a mistake?" She asks nervously.
You hook your hand behind her neck and pull her in for one last long kiss. You look her in the eyes. "Casey Devlin. Would you do me the honor of going on another date with me?"
She smiles sweetly and breathes a sigh of relief. "I would love to Jesse Bailey!"
You grin back, your heart aglow with joy. "The next one will be better. I promise."
She giggles and strokes your cheek. "This will be hard to top."
You hug her.
You wipe your seat off with your jacket. Casey gets in beside you and covers the leak with her hand once more. Her other hand sits on your thigh, her head resting on your shoulder.
You put the old car into gear and roar off toward home.
What's next?
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Runt of the Litter
You've got the smallest cock in your family...and you're the only man!
You're family has a few BIG secrets. A Futa-SPH- Story.
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Updated on Jun 28, 2025
by grimbous
Created on Apr 20, 2023
by grimbous
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