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Chapter 31
by RachelDaws
Will they return soon?
Right after Dessert
The stunned look onTrent’s face didn’t stay that way for long. Sensing the moment of weakness, Jessica dove in and latched her lips onto Tiffany’s. Jessica’s long tongue slipped into her partner’s mouth using the element of surprise to give her access. The appendage spent time slowly exploring each and every cavity within it as it wrestled with Trent’s own wet tongue. While she assaulted his mouth with hers, she pushed the feminized man up against the door and took control over the embrace.
Trent’s mind was firing two different signals. The first and certainly strongest of the two, was that his highschool crush was making out with him. This exact moment, well perhaps not exact, had been the fodder of so many jerk off sessions that it felt like he had single handedly kept Kleenex in business through his highschool years. The second signal was that the woman he had been crushing on wasn’t a woman, that statement rang hollow the second he allowed any sort of self-examination to brush against the concept.
Deedee had been firmly categorized as a woman in his mind for the last day at least, and he had been faced with her impending erection only hours ago. Of course the lust that was so pervasive within him helped to silence that malignant thought. The past half hour of teasing at the hands of Deedee and Jessica had his body revving like a track car as he stood there. And while he could certainly feel the cage Jessica had on now that he knew to look for it, he could also feel her soft pillowy lips on his. Her very large and very real breast on her chest as she pushed up against his own protruding chest caught his attention as well. The feeling of her smooth legs rubbing against his own denuded stems sent electric sparks through his spine into his brain. Each shock began eroding any reason his mind could conjure to stop the petting session with each successive feeling.
With his hands around her hips, he slipped them back around the rotund globes and attempted to do as he had been instructed. The tips of his fingers slipped under her skirt in search of any buried treasure. The long nail extensions brushed up against the gem of the metallic plug as he searched her. The blonde moaned into his mouth as he pressed against it lightly. Pulling back from the deep kisses, Jessica smiled as her eyes blazed with lust. “Ohh, I can play that game too!” Her own hands skipped the playfulness she had displayed earlier of slipping under garments and simply pulled his skirt up around his waist as she reached around in search of the plug inside of him.
Staring into each other’s eyes, the two blondes moaned and made out while playing with each other’s plugs. Trent’s breath came hot and heavy as they finally broke the kiss. Jessica spoke up as she pulled away after licking his painted lips in a parting gesture. “You are so much cuter this way.” Her eyes locked onto his to see how he would react as she continued to put subtle pressure through his plug.
Trent’s mind snapped back as he realized what she had just said. The whole truth of his situation, of her situation all crashed back into him. Yet this time, the cushion of lust and desire spread the impact out so much that it was almost non-existent. “Like, you’re just as amazing as I knew you would be Jessica.” The valley girl speak had become pervasive enough that even now he didn’t slip out of it. Or perhaps it had been Jessica’s enforcement of his current appearance that made it come naturally.
The tone of reverence from the cute sissy in her arms made Jessica giggle softly. She didn’t want to hurt his pride much more than she already had. She had explicit instructions on the game she was to play. It was a new one for her. While Rachel and she had played many games over the years, this was the first time she helped in recruiting another person like her. “If you think this is fun, just wait till it is more than a plug.” Leaning in, she began to **** his lips before he could speak up and ruin the moment.
The pair’s hands slipped all over each other as they continued to use their tongues like they were seeking buried treasure in each other’s mouths. Trent could feel his cage as it limited his feeling and kept him as soft as it could. The worst moment of dealing with his lack of ability to show his excitement physically was when he finally got his hands on the beautiful woman’s breasts. Slipping one out, he tweaked the nipple softly as it hardened in his long nailed hand.
Feeling a giggle in his partner, he should have known that something was about to happen before both of her hands crept from his ass and slid up to grasp his own mechanically sensitized nipples. The computers within his glued on breasts fired up as she played with both of them. Her fingernails and fingers flicked across them. The nubs were already poking through the thin lace bra he had selected and the attention only made them more visible. Moaning into the kiss with Jessica Trent surrendered himself to the feelings that kept crashing into his mind like the waves of a tsunami. The pair of them lost themselves in the touches and caresses. Time became less of a concept as it ticked on.
A sudden knocking at the door shattered the paradigm the pair had allowed themselves to slip into. A deep smooth voice slipped through the locked door. “Excuse me, ladies? I hate to interrupt like this, but Rachel asked me if I could come back and check on you? She said that Jessica was going to want to order dessert and that now would be the time to order it.
The pair were staring into each other’s eyes as they listened to Tony’s voice. Hearing his explanation, it was all Trent to do to keep standing as Jessica grabbed his shoulders and pulled him away from the locked door. Her finger’s opened the latch quickly and she opened the door. Both of Jessica’s prodigious breasts had slipped from her short white strapless leather dress and sat exposed as she gestured for the black man to enter.
“Huh.” The monosyllabic response seemed to be the only thing Tony could get out as he stepped into the room. Seeing the man make his way through the doorway, Trent realized his skirt was still hiked up past his hips and struggled to shimmy it down. Thankfully the light and flowing fabric cooperated well before Tony could get a visual that Trent would do anything to avoid. Once Tony was past the point where Jessica could close the door, she did so quickly and snapped the lock back into place.
“I want chocolate. Creamy, and hard.” Jessica’s voice was thick with lust that Trent had never heard come from her. Looking over at the blonde he noticed something that he had never seen before. Nestled between her breasts was a pair of tattoos. The black symbols stood out against her lily white skin in stark contrast allowing the small spade symbols with the letter Q inside of them to be easily seen now that her full breasts were exposed. Tony’s eyes seemed to have caught the sight as well as he chuckled and shook his head.
“Gotta love a snow bunny.” Reaching out, he hooked one hand around Jessica’s neck and pulled her into him for a deep kiss. Trent stared on as the strong man took control of Jessica faster even than she had taken control of him when they had first arrived in the bathroom. Her long nailed fingers didn’t fumble in the slightest as they shot forward and began to undo his belt and lower the man’s work slacks. “Damn girl, you aren’t shy are you?”
Jessica’s eyes blazed as she shook her head and pushed the man backwards so that he was leaning up against the sink. “Stay.” She giggled as she stepped away while his pants fell around his knees. Moving over to Trent she kissed him softly on the lips. The taste was different than it had been a moment ago, there was a taste of the man on her lips that hadn’t been there. Slipping past the kiss, Jessica leaned in to whisper in his ear. “Deedee will fucking kill me if take her first away from you, but you can’t just stand here. Come with me and you won’t have to do anything ok?” Pulling back from the whispered conversation she stared into his eyes until he responded with a nod in affirmation.
Wrapping her hands around his, she pulled him across the small bathroom till they both stood in front of the large man. Trent only realized just how tall Tony was now that he stood before him in his heels. While certainly not as tall as Tre had been, Tony appeared to be around the same height Jax had been. Only it wasn’t his height that got to Trent the most, instead it was the fact that both Jessica and himself could stand side by side in front of the man and still feel dwarfed by him. A shiver ran through him as he prayed that they would be able to pull this off and keep the large man from becoming upset.
“My friend is shy, so she is just gonna watch ok hun? But I promise, you won’t even notice.” Giggling, she began to crouch down. Squatting down she rested her round ass against her raised heels. Seeing that Tiffany had not followed, she reached up and pulled him down next to her with her left hand. Her right hand reached out and began to pull the boxers that covered his expanding member down. Following Jessica’s lead, Trent crouched down and stared ahead. It was only as the hardening cock flopped out as Jessica lowered the man’s underwear that he realized just how close she meant for him to be to the action.
With only his own tiny cock, porn, and the recent experience with Deedee’s to judge on, the hard meat shaft that flopped in front of him put two of those to shame. The thick shaft looked to already be at least as long as Deedee’s had been at full extension. It was already twice as big around, and appeared to still be growing in length. The dark shaft bobbed in between Jessica and Trent’s faces.
Her eyes locked onto Trent’s as Jessica leaned forward and ran her tongue across the spongy glans. Her eyelids fluttered as she moaned into the air. Still holding onto Trent’s hand, her other hand reached up and pushed the hardening shaft up against Tony’s stomach. Tearing her gaze away from Trent, she locked eyes with Tony and leaned forward. Her long lithe tongue started at the base of the man’s balls and traveled the entire length of his shift as she spread spit across the whole underside of the cock.
Upon reaching the tip she smiled and simply dove down onto it. Bobbing up and down on it, she took it inch by inch deeper. Her pink lips covered more and more of the shaft as she aggressively inhaled the cock in front of her. Her free hand slowly began to jack the base of his shaft off as she worked to pull the entire cock inside of her.
Trent stared at the porn quality blowjob in front of him in awe. The few girls he had convinced to suck his tiny cock had complained the entire time. This was the farthest from that experience that he thought something could be. Jessica moaned with each downward thrust, the sounds that came from her mouth sounding like only the hottest of blowjob videos online. The earlier **** he had endured had heightened every sense Trent could feel and the sounds that drifted into his ears brought even more desire with them. As he crouched in heels and a dress he began to pant and stare at the masterclass blowjob that was happening in front of him.
Trent was in awe as Jessica simply continued to bob farther and farther down onto Tony’s hard cock. When she suddenly stopped bobbing he thought something was wrong before he realized that she had completely taken the rod to the hilt. Her nose pressed up against Tony’s pubes as she stared up into the man’s eyes and reflexively swallowed around his shaft. Tony’s expression of awe was reflected in Trent’s face as the black man spoke up. “Holy shit. You fucking love this don’t you? I have never seen someone do that so fast. Especially a white girl.”
Pulling off the cock lodged in her throat even Jessica’s prodigious skills couldn’t stop the **** reflex as spittle dripped from her large soft lips. “I never miss dessert Daddy. Will you feed me Daddy? Please?” Leaning her face up against his cock so that his balls rested on her chin and the shaft lay along her nose, she looked into his eyes as she begged him to feed her his dick. “I’ve been a good girl all day, and I am so fucking hot for you Daddy.”
Realizing that he didn’t have much time to enjoy the bounty that had been bestowed on him, Tony nodded. His hands settled on either side of her head as he laced his fingers through her blonde tresses. The smile that she bestowed on the man in front of her was so happy that Trent wasn’t sure he had ever seen anything like it from her. “Fuck my mouth Daddy!” The blonde’s words reverberated through the small bathroom as she dove back onto his cock.
“Usually I aim to please, but I don’t have time for that tonight. If I did, I’d show both of you exactly how good this dick is. Instead, I think I’m just gonna aim to feed.” Staring down at the two beautiful women crouched in front of him, Tony slowly began to pull Jessica’s head up and down on his hard shaft. The gluck gluck noises that filled the room as Tony face fucked Jessica rattled around in Trent’s mind. It wasn’t just his hearing that was assaulted either. There was a scent to the room, the smell of sex and saliva filled the air. There was also the feeling of spittle, and perhaps some other fluids that slapped against his face as his front row seat kept him in the splash zone.
Having four of his five senses battered with cock while still riding the high of his makeout sessions with Jessica had Trent reeling. He wanted to be repulsed by the cock in front of him. He wanted to hate this whole thing, crouching down in front of a man as his crush held his hand while she swallowed another man’s cock like a porn star should have fired an anger within him. Instead all it did was fan the flames of lust that had been ignited.
Tony’s hands began to work Jessica’s face up and down his shafter faster and faster. All three of them could sense the impending explosion. Sensing that it was growing closer, Jessica tensed and dove her face to the hilt, once again taking him into her throat. Swallowing her throat to try and coax the cum from the erection inside of her, her hand around Trent’s clenched as the air in her body slowly started to run out. Suddenly Tony let out a groan and began to pump his seed into the blonde’s throat. Slipping up off the shaft slowly as each pulse landed inside of her, the skilled cocksucker managed to collect a number of shots within her mouth without spilling a single drop.
Jessica’s breath raged in and out of her nostrils as she tried to get control of her faculties again. Closing her eyes, Trent could see that she was swishing the cum around inside her mouth as if she was tasting a new wine that had been brought to the table. Opening her pink lips and her eyes, she first showed Trent the large white globs of fluid on her tongue. Turning to look up at Tony she waited expectantly and stared up at him, her tongue dancing through the liquid.
Tony’s voice and lack of understanding showed just how young he likely was. “Do you need me to move so you can spit?” Shaking her head at the young man raised an eyebrow as she continued to wait. A look of confusion rolled through Tony until he realized that she was waiting on him for something. “Are you seriously asking me what to do with it? Swallow it slut.” A visible shiver of pleasure rolled through Jessica as she closed her eyes and lips and swallowed the huge load down.
“Thank you Daddy. You have a wonderful cock! So ummm, can you go now so I can clean up?” Jessica’s playful giggle almost seemed out of place with the aggressive and lustful pornlike performance she had just executed.
Tony’s voice was full of surprise as he pulled his pants and boxers up into place. “You are one crazy slut. But you suck dick like you were born for it.” Jessica’s full throated laugh caught Trent out, every woman he had ever met would have taken that line as the ultimate insult. Instead, Jessica seemed to revel in it. Both feminine presenting people stood from their crouch, their thighs and knees complaining at being locked in the uncomfortable position.
“Cause I was born for it, Daddy. Thanks for your yummy cum!” With those words, Jessica essentially ignored Tony and dove into her purse. Pulling out makeup she began to try and find a way to repair the mess that was her face. “Tiffany, you need to do this too, babes. I kissed off all that lipstick.”
Tony’s head shook in complete surprise at the scenario that had just played out as he slipped from the bathroom. Trent moved up to stand next to Jessica and opened up his purse to see what he had available to him to match what Jessica was pulling out. Looking at the various cosmetics in his bag, he realized how out of his depth he was. “Um, like, Jessica?”
“Yes honey?” The blonde was quickly and expertly washing her face clean and reapplying the lipstick and mascara that she had lost.
“Like, I don’t know how.” Turning to look at Trent, Jessica only laughed before she jumped in to help him out. Looking through what he had in his purse, she pulled a few things out. With a smirk, she leaned in and kissed him deeply. Not even thinking about what had just occurred, Trent opened his lips and accepted her tongue. Now that his fifth sense was brought to the fore, he suddenly realized that the slimy taste and feeling was the residue of another man’s cum as a small amount was pushed into his mouth.
Trying to pull back from the kiss as he realized that the taste was another man’s cum, Jessica’s hands slipped up and locked his face against hers. Slowly becoming used to the sensations and taste, Trent quickly fell back into the lust and desire that her lips inspired within him. Just as he was becoming comfortable with the whole thing, she pulled back and giggled. “No more kissing! We gotta fix our lips, and like everything else.”
Five minutes later saw the pair working their way out of the bathroom. Holding hands, they walked through the hallway towards the restaurant. One of the female servers stood there staring the two girls down. It was obvious from the look on her face that she knew exactly what had gone down and did not approve. Jessica turned to Tiffany and winked before turning back to the other girl. “Jealous?”
Trent’s eyes shot open in surprise, and then the laughter followed as he saw the incredulity and anger spring up on the woman’s face. The bright red shade that crept up from the neck of her collared shirt only made the pair giggle together more as they made their way back to the table.
What is next for our Fearless Foursome?
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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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