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Chapter 32
by RachelDaws
What is next for our Fearless Foursome?
Driving home
Rachel’s back was to the approaching figures as Jessica and Tiffany made their way back to the table. The pair were thick as thieves leaning on each other and giggling like they shared a joke that no one else on the planet could take part in. The mirth on Tiffany’s face made Deedee’s heart soar. Her thoughts centered on the conversation she had just finished with Rachel and a new plan formed in her mind.
Standing up as their dates approached, both Rachel and Deedee took their respective partners in hand and kissed them. Deedee had planned for her kiss with Tiffany to be softer, more benign. Instead, Tiffany’s lips parted with almost no thought, the building pressure in Trent’s mind was searching for any means of release. With no resistance, Deedee’s tongue dove into his mouth. The pair pushed into one another, losing themselves. Only a giggle by Jessica and Rachel clearing her throat brought the two back to reality.
“Well ladies, I think this party may have surpassed the public portion. Perhaps we should retire to your house Deedee?” Rachel’s smile was that of a wolf staring down her prey. “It seems Jessica has already skipped ahead of the rest of us and had her dessert. I think I could go for something as well, but I tend to prefer a different type of delicacy.”
The comment on dessert brought to Deedee’s mind that Tiffany’s mouth had carried a small taste of something she hadn’t expected. Looking her son in his eyes, she asked him directly. “And Tiffany baby, did you have dessert too?”
The look of confusion on Tiffany’s face should have been an answer, but Jessica jumped in and spoke up. “Nah! We just made out after. So it’s all dessert by proxy!” Rachel and Deedee’s eyes met and both women shook their heads in fascination at how much Jessica enjoyed the slut that she was now.
Trent’s cheeks flushed red as it finally dawned on him what exactly dessert was a euphemism for. Of course, that meant that he also realized that it meant that Deedee had just tasted another man’s cum on his lips. A deep swallow caught in his throat as he realized that meant that he was swallowing the taste of another man. Reaching down to his half empty wine glass, his manicured nails wrapped around the stem and he drained it quickly. Setting the glass down he saw that his recently painted lips left a bright red imprint on the glass and he felt his reality shake again.
The rest of the party seemed to ignore Trent’s sudden crisis and laughed amongst themselves as they made their way out of the restaurant. Rachel had settled the bill while Jessica and Tiffany had been in the restroom, allowing them to proceed directly out. The sight of all four feminine figures walking out of the store, the two different pairs holding hands to show they had coupled up, certainly drew a number of stares from everyone. The four different sets of heels sounded like a rapid fire machine gun as they struck the hard ground at different intervals.
Trent began to feel the wine hitting his system, realizing he had not had much to eat in the past day. Swaying slightly more than he intended, Deedee took notice and pulled him closer, her arm wrapping around his shoulder in a protective manner. “Careful hun. Your wine going to your head?” The nod that Trent returned sent his platinum blonde hair bouncing around him.
The pair of couples separated, agreeing to meet back at Deedee’s. With Rachel and Jessica walking off to slip into Jessica’s bright pink Mustang. Trent did notice that Jessica slipped into the passenger side instead of the driver seat and he thought that was odd considering he was sure that Jessica had imbibed less wine than the other had. Shrugging, he suddenly realized that Deedee was holding the door open for him at her own car. As he slipped carefully into the seat in a practiced manner, Deedee stepped over to her own side and sat down as well.
A sigh of relief escaped Deedee’s throat as she could finally let her control slip now that the door was closed. Turning the car on, she looked at Tiffany, Deedee smiled and shook her head before pulling back out of the parking spot. “God damn babygirl, you have no idea how much you have been teasing me do you?” One hand on her steering wheel, the other fell down to her skirt and massaged the hardon forming in her incredibly tight short dress.
Tiffany, having just gotten done with a close encounter of another cock, turned and looked over Deedee. Where Tony had been a statue of masculinity, Deedee was something totally different. The bulge in her skirt was the only thing masculine at all about her. The tent that was beginning to grow drew his attention in. Deedee glanced over and saw that Tiffany’s eyes were locked on her lap and a smile grew. Reaching over she took a hold of his hand and brought it to her smooth thigh. If either had been able to see themselves in a mirror it would have caused more than a hint of laughter as they both chewed their bottom lip in efforts to keep their moans stifled.
“Do what you want baby, we have a short drive then we can see if we can have some fun together.” Her own free hand left his there and slipped over to settle on his own knee, her nail tips drawing lazy circles in the soft flesh just below the hem of his soft skirt.
Trent studied his own long nailed hand on Deedee’s thigh, much higher than hers was on his own leg. His own fingers mindlessly began to stroke her skin. Because his gaze was locked onto Deedee’s engorged member hidden by her skirt, he failed to notice that Deedee aimed the car for a speed bump as they pulled towards the main street. The sudden bump **** Trent’s body deeper into this seat and shoved his plug deeper inside of him at the same time. His jaw dropped open as it hit a spot that felt new. Deedee took the distraction as a chance to slide her own hand higher up under his skirt.
Recovering from the bump, Trent looked over to realize that his hand was no longer gripping Deedee’s thigh. The white cloth covered joystick throbbed in his hands. Freezing as he realized that he was gripping her cock again, he sat there just staring. Pulling up to a stoplight, Deedee’s hand on the steering wheel fell down to grip his wrist off her cock. To his surprise she didn’t give it back to him, but simply wiggled her hips. The motion slipped her already short skirt up enough that her cock slipped out from under it. Placing Tiffany’s hand on her now exposed dick, She groaned out. “Oh god yes baby.”
Trent’s lips parted as he felt the heat of her exposed member in his delicate hand. Her own hand toying with his cage began a rhythmic stroking. The rhythm seemed to take over his soul, and the next thing he knew he was sitting there slowly jerking off the cock of his feminized father as she drove him home. His breath began to speed up as he realized how good it felt. Stroking Deedee’s cock was a completely different experience than his own tiny dick. He was lucky to get his thumb and two fingers on his, while on Deedee’s he was able to wrap his hand around the whole thing and still have room to stroke up and down.
Still stuck at the light, the roar of an engine pulling up next to them stole Deedee’s attention long enough for her to let out a giggle. “Wave hi baby! It’s Rachel and Jessica.” Deedee pointed across to the bright pink muscle car sitting next to them. Somehow, Trent didn’t even think to pull the hand off Deedee’s cock to wave, instead raising his other hand. Turning to look, he saw Rachel’s smiling face, but Jessica was nowhere to be seen. As he waved, Rachel looked over and noticed who was in the car next to her.
Instead of returning her own wave, she reached down and grabbed a fistful of the blonde hair in her lap and pulled Jessica’s face up to look directly at Deedee and Tiffany. Jessica’s smile was marred with spit that dripped from her plump lips, the makeup she had carefully reconstructed after being face fucked by Tony had all but disappeared. Jessica’s eyes slid into focus and she smiled and blew Tiffany a kiss before her head disappeared down into Rachel’s lap. As the light turned green, both cars pulled off the line carefully.
Still stroking Deedee’s cock, Trent tried to puzzle out how eating a woman out as she drove would work out. Not that he had the most experience using his tongue. Still, it seemed a difficult and odd proposition. It wasn’t till he looked back at Deedee’s stiff cock and noticed his pink nailed hand was still stroking it that he realized just how crazy his night was about to become. “Like, is Rachel like us Deedee?”
“More like me than you baby. She would never be caged up.” Sitting there, Trent let that thought percolate in his mind. He still couldn’t believe he had asked for all of this. Deedee had sworn to him that he had begged for her to do this to him. Even now that he was finding parts of this life as things that he didn’t completely hate, he had no idea how that sort of situation would have happened. His wandering thoughts kept him preoccupied enough that he simply kept rubbing on Deedee up until they pulled into the driveway. Suddenly realizing that any sharp eyed neighbor would have been able to see that, Trent ripped his hand back like something had bitten it.
Deedee simply pressed the button for the automatic garage door and pulled the car inside. Pressing the button to close it, she leaned over and kissed Tiffany on the lips softly. “Come on baby, let’s go greet our guests.”
Who else wishes they could be in that room?
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Sins of the Father
From father and son to couple.
Trent comes home to find his father Derek is now Deedee, his crossdressing sissy father. After a fight, Deedee decides to show Trent that maybe he isn't as manly as he thought he was.
Updated on Oct 4, 2024
by RachelDaws
Created on Apr 13, 2024
by RachelDaws
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