This story is a work of fiction and contains descriptions of explicit sexual acts of a young man discovering his sexuality. It contains graphic scenes of sex between a man and his adult son as well as depictions of the consumption of various illegal substances. If this type of content offends you or you are under the age of 18 do not read it.
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Chris and Zesty: Playdate with Mom and Dad
A Match Made in Pervert Heaven
Chris had known about his dad's homosexual desires for a while now. He had been using the old man's computer one day and when he happened to look through the browser history, he found his dad had been visiting a lot of gay and tranny porn sites. Poking around in the contents of the hard-drive soon revealed a clumsily hidden trove of sexy selfies in women's lingerie.
The young man had
become perversely aroused by the pictures of his dad dressed like a
cheap whore. The man had a very small penis, barely three inches
erect and just a clitoris-like nub when it was soft. Clearly
submissive and clearly in need of a good fucking, Chris was surprised
to find himself seriously turned-on by his old man. It wasn't long
at all before he started contemplating giving his sissy dad exactly
what he so obviously longed to receive.
Things might never have progressed any further but for a chance meeting one night on a porn sharing website. Wanting to explore his new feelings and desires Chris had begun spending time surfing porn sites looking for transvestites and cross-dressers. He eventually created a profile of his own and came to know a particularly filthy and outgoing sissy slut with the unlikely nickname of misszestymordant. She had encouraged him to open up and he had immediately shared his father's sexual habits.
Zesty had been really turned on by the young man's revelation and expressed her newfound desire to fuck his sissy dad with him. They hit it off immediately and spent hours the first night role-playing together. Arousing and exciting each other until, despite being over a thousand miles apart, they had experienced practically simultaneous orgasms.
Their camaraderie and sexual complicity grew quickly. They found themselves growing fast friends despite the fact that middle-aged Zesty was about thirty years older than young Chris.
Fantasizing together about having sex with their respective parents and various others was good fun for the pair and Chris was growing more comfortable with his own attraction to sissies and transsexuals as well as his desire to explore other homosexual experiences, complicated as it was by his small town life. The more he opened up the hornier he got and the orgasms were absolutely dynamite, but the fact remained he was still a virgin and he was dying to feel his cock penetrate something for fucks sake. His next big surprise was to discover within himself a desire to feel a cock in his hands and mouth.
Sharing his frustration with Zesty she promised to help and began making plans to get out to Saskatchewan from the West Coast where she lived to help the young man seduce or otherwise overpower his dad so they could have their way with the closeted fag.
Accessing his father's PC again, Chris found out his dad had a number of interconnected online profiles on porn-sharing websites where he posted his pictures. John, as Chris's dad was called, went by the name Jenny when he posted his sissy photo's. Chris was surprised to find they actually had accounts on the very same site but Zesty had suspected from the first that this would turn out to be the case. She was hip to that whole reclusive closet homo lifestyle, having lived it herself after all.
His online activities provided a convenient opening to become acquainted and eventually set up a meeting. Zesty made contact and proceeded to chat him up and in a sense "groom" him over a period of time. It proved almost pitifully easy to befriend the sex-starved sissy dad. By asking leading questions she had learned he had a more than passing interest in incest and had at least contemplated bestiality. She had a deep desire to be dominated and subservient, which Zesty cultivated. After about six months of getting to know each other in what seemed a natural way with cam-chats and cyber-sex, Zesty judged that he was primed and ready for physical intimacy of the BDSM kind. Eventually under pretext of a trip to Montreal to see some family, Zesty proposed a real life hook-up as she drove across the country.
The night finally arrived. Zesty had rented a motel room outside Regina and arranged a meeting there with the young man's sissy dad. Seductive saxophone music by Euge Groove was playing on the laptop she had brought and a camera on a tripod was set-up to capture the night's festivities. All dolled up in leather dominatrix gear that left her hard cock and soft ass bare and ready for action. Smooth all over, Zesty was wearing a long haired, bright orange wig and make-up. That's when the submissive slut knocked at the door.
The camera was obliquely pointed at the door as she pressed the record button before moving to answer. Legs firmly planted, a riding crop in her hand, Zesty opened wide.
As instructed, the bitch was in drag. Wearing a tight, short, slutty skirt with a slit up the sides. It barely covered her bare ass and little clitty-cock. Garter belt straps held up fishnet stockings on her too skinny legs. Her fat saggy man-boobs rested on the round belly that poked out under her halter top. She had on a long blond wig and slutty make-up, inexpertly applied. Despite her nervous glances, Zesty could tell that she was extremely turned on by this strange new experience and anticipating a real life sissy experience.
"Come in bitch. I've been expecting you." Zesty said.
She scuttled in and uttered a strangled yelp when Zesty switched her ass lightly and playfully as she passed.
Zesty giggled and shut the door. "I wasn't sure you'd show up."
"I wasn't sure either. But here I am."
"Here you are. I just love that thrift-store-chic outfit, bitch." Zesty approached slowly, her hips swaying. She grabbed the plump sissy's face and kissed her full on the lips as the other hand dipped under her skirt to squeeze her little package. The slave bitch who was Chris' dad moaned like a bitch in heat and responded enthusiastically, thrusting her junk into the grabbing hand and opening her mouth to let in Zesty's probing wet tongue. "Yeah. You like that don't you? Fucking cheap whore." Her hand came away wet and sticky with seminal fluid, indicating the extremity of the repressed sissy's arousal.
When she tried to touch her, Zesty swatted the bitch's hand away and said. "I didn't say you could do that! You will call me mistress and never show any initiative or you will be corrected. Understood bitch?"
"Yes Mistress." She answered docilely.
"That's right. You are just beginning your training bitch but trust me you will not regret coming here tonight. And you will never be the same after this. We have something very special in store for you."
"What?" She asked. Beginning to look a little worried.
Zesty swatted her ass again. Harder this time. "I told you to call me Mistress! And no fucking questions whore. You'll find out in due time. Now let's take a few pictures before we get you tied up on the bed." Grabbing her arm Zesty led her toward the bed. She stumbled slightly in the high heel boots she was still unaccustomed to wearing. "Stand here and do as I say."
"Yes Mistress." The sissy answered, unsure but obedient regardless.
Zesty went to the camera that had captured the arrival and greeting and swung it around toward the sissy. She was holding her hands together in front of her belly and fidgeting nervously.
"Now give me some sexy poses bitch, show me what you got."
A little hesitantly at first but gaining confidence as Zesty encouraged her, she started posing and twirling, flashing her ass, bending over and squeezing her cleavage at the camera like a sex symbol.
"Thats it bitch, keep it up." The dominant sissy said as she let the camera roll and went over to the desk. She loaded a little glass pipe with a little rock of crack cocaine, primed it and smoked a quick hoot, drawing deep and holding long before she blew out her breath in a long rush of funky smelling smoke. She reloaded the little pipe and went over to the bitch who was looking at her intently, frozen and staring. "Smoke this, bitch." Zesty said plainly but with authority as she poked the pipe into her mouth.
"Yes Mistress." She answered around the pipe.
Zesty's lighter clicked and the bitch drew her first hit of crack. "Now hold it in until I tell you to blow out and I'm going to suck your little clitty for you. This alone is worth the price of admission and it's only the beginning." She knelt and took the wet little cocklet into her mouth. Sucking hard as she kneaded her slave's chunky ass, Zesty gave her pleasure sensations that she had no idea even existed.
Pausing a bare second, she gave the signal. "Now exhale bitch."
The rush was incredible and Zesty caught and swallowed a thick load of cum. The slave bitch moaned and collapsed backwards onto the bed behind her, swooning like a Victorian Dame in a too-tight corset.
Zesty stood and spit the load into the passed-out bitch's face. Turning, she adjusted her outfit and wig before facing the camera. "And that's how you do that." She said simply.
Turning the stereo volume down slightly, she repositioned the camera and zoomed out to capture the desk as well as the bed and the space in front of the door and let it roll as she got out her cell phone and made contact with Chris, her young co-conspirator. He sounded nervous but very excited at the prospect of this evening's activities. Zesty gave him the address and room number and told him his slave would be ready for him. She snapped a few pics of the passed out whore on the bed with a load of cum drying on her face and sent them to him.
Zesty knew she wasn't quite done yet, the presentation needed to be perfect. Smiling gently, she turned the volume back up, got some leather straps and cuffs from her bags and went to work. She hummed along to the sexy tunes pouring out of the speakers. It was a labor of love to her, it truly was.
When he entered the motel room Chris was almost vibrating from the incredible waves of sexual energy that coursed through his body. His cock had immediately gotten rock hard when Zesty called to let him know their plan was on track and his raging erection had not left him since. The wicked correspondence with that nasty sissy had been feeding his twisted appetites for months and now he was finally going to get some real satisfaction. All unknowing, the man who had fucked his mother was trussed up in bed, dressed like a cheap whore, begging to be bred by his son's throbbing penis.
Crouched on the bed, the slave bitch was bound wrist-to-ankle and blindfolded, with her ass facing the door. The knock on the door of the hotel room followed by sounds of entry and quiet greetings unseen behind her, ratcheted her sexual tension up another notch, something she would have thought impossible at this point. She felt a blob of pre-cum force it's way out and hang for a second on the tip of her puny clitty-cock before dripping to the already soaked sheets on the bed. She heard her new Mistress and the young man making out behind her, the sounds of clothing being hastily removed and dropped to the floor. He reached out tentatively and caressed a penis for the first time, marking the first of many fantasies to come true for him that night. The bitch on the bed couldn't see but the naked boy was remarkably hairy and Zesty enjoyed the feel of it against her own smooth depilated skin.
As yet unaware of the identity of the man Zesty had arranged to fuck her,she only knew that he was a much younger man who would be having his very first sexual encounter with a sissy. It pleased her to think that her anal cherry would be popped by a young virgin stud.
Now the sounds coming from behind her were unmistakably those of a blow-job. The boy was moaning softly accompanied by slurping sounds of mouth on cock. Her new Mistress had told her the boy was hung, too and now it seemed she was taking advantage of her position to exact a salty toll. Never in her wildest imaginings could she have conjured up as filthy an experience as the one Zesty had cooked up for them all from over a thousand miles away.
The drugs were a completely new thing to her. Mistress had given her a sniff of poppers after the crack and it had made her feel like her skin was on fire and every touch a raging inferno of sexual desire. Behind her the young man gasped as he shot his load into Zesty's talented mouth. She found herself drooling with anticipation. Fully aware that she had crossed the point of no return, she was a sissy slut now and she found herself loving it; craving the final step that would make her a full-fledged sissy-slave. A real man breeding her like the bitch she was.
Taking care to not reveal Chris' identity, Zesty refrained from using his name. "There you go loverboy. Now you can be sure the experience will last and both of you will enjoy it. If I had let you go charging in there you would have cum right away. And where's the fun in that?" Zesty said as she stood up.
"That was absolutely amazing baby. And I guess you do know better." The young man answered with a slight tremor in his voice as his knees quaked visibly.
On the bed, the blindfolded whore found the voice oddly familiar but dismissed his first thought as ludicrous. There was no way that could be Chris. He was so obviously straight after all.
"Let's smoke a joint and do a few hoots on the glass pipe. This bitch can await your pleasure, that's what a good slave does." Zesty slapped her ass playfully before running her finger around the highly sensitive sphincter, eliciting startled squeals of mingled fear and anticipation. Grabbing the young man's semi-hard penis she pulled him willingly towards the little desk where the drugs were laid out.
They made an effort to remain quiet as Zesty proceeded to get them all into the zone. Without forgetting the slut on the bed of course, who took every puff off a joint and sucked greedily on the glass pipe whenever it was pressed to her lips. She rounded it all off with a round of stiff Black Russians. She put one drink down in front of the bitch and stuck a straw in her mouth.
Chris was once again showing signs of arousal and Zesty judged the time to deflower the whore had arrived. She had been slowly caressing and kissing him back to readiness as they imbibed. She knew what she was doing and Chris was now aflame with ardent passion.
Grabbing his pulsing member she pulled him toward the waiting sissy. Chris followed willingly.
Zesty rubbed the nob of Chrissy's cock with her thumb, pressing hard to squeeze out precum and spreading it all over the head. The young man shuddered and they kissed again, standing directly behind the bitch.
Pulling him closer she rubbed the tip of Chrissy's cock in the crack between his daddy's chunky cheeks. All three of them moaned in unison as Chris and his dad shuddered. If she hadn't blown him when he came in the boy would have shot his load right there. As it was the flow of seminal fluid increased and the crack quickly became slick and slippery.
The bitch had never had an actual penis inside her but she had been dildoing herself for more than a year so there was no question of breaking her in. When she guided it to the sloppy hole, Chrissy's cock just slipped right in all the way to the base. Again they all moaned in pleasure and delight.
Zesty left them to their own devices and went to man the camera. Taking it off the tripod to walk around and take close-up shots of the crazy homosexual incest action she had whipped up in their Saskatchewan motel room.
"There you go bitch. You are really and truly a sissy now. How does it feel?" Zesty inquired.
"Oh Mistress it feels wonderful! I can't believe it's finally happened. I've dreamed of this since I was young man. More than thirty years."
Chrissy was shocked to hear his dad had been a closet sissy since before he was born but he just kept fucking, his hands caressing the sissy body crouched under him. Resting on the broad back that had once given him horsey rides, Chrissy's hands reached around to caress her silk covered tits and belly. Squeezing and rubbing as his hard cock thrust and ground into soft pliant ass.
"Your ass-cunt is a pleasure to fuck, bitch. Nice and loose. Your Mistress has offered to sell you. Do you want me to make you mine?" Chrissy whispered into his sissy-dad's ear.
"Oh my god Master! You are fucking me so beautifully. I would do anything at all you wanted Master if it meant you would fuck me like this." The slut answered breathlessly.
"And what about your wife, bitch? Does she come as part of the package? Are you gonna be my sissy cuckold slave-whore?"
"YES! Of course you can fuck her as much as you want." She had until that moment completely forgotten that she was married but she would have said yes to anything right about then. "I'm sure she is starving for a real cock after so many years married to a tiny limp dicked sissy like me. She knows I'm a sissy, too. I got caught all dressed up a few months ago and she has been threatening to divorce me."
"I think we're going to have a whole lot of fun my fat little whore." Chrissy reached down and unshackled the bitch's wrists from her ankles, freeing her to move around. "You belong to me now and so does mom."
"What?" The bitch froze but Chrissy just kept plowing into her.
"You heard me. You are my bitch now daddy and so is mom. Now turn over on your back so I can slap your useless clitty as I finish cumming all over you."
Her hands free now, the sissy reached up and removed her blindfold, turning to face her son. Shock on her face as she looked at Zesty and the camera.
"SURPRISE!" Zesty yelled out cheerfully with a wild giggle.
"Oh Chris... I am so ashamed." The whore blushed crimson and closed her eyes.
But Chrissy was still hard as steel and raring to go so he reached out and pulled her roughly into position at the edge of the bed. He rested her ankles on his shoulders and slapped his fat cock into that puny little dick a few times before sticking it back into her pussy whereupon the bitch's eyes flew open and she murmured her son's name as her lust overcame all reason.
Chrissy had been rehearsing these scenarios for months with Zesty and he knew exactly what he wanted from his sissy-dad. He was in control. "Yeah bitch, things are going to be very different now. Wait `til you're watching me fuck mom. She will love it, too. We are taking this family to a whole new level. You dad, you will be my dutiful sissy cuckold bitch and mom will be my sex-slave and you will both learn to fucking love it." His cock deep inside, grinding hard into her soft ass-cunt. Making her moan and groan loudly. So close now to shooting his load deep in her bowels.
The bitch who had previously been his dad looked up at him, speechless. The camera captured every moment of amateur porn gold as Zesty flitted around. "You are both so fucking hot." She said with passion. Putting the camera back on the tripod, she moved to join them on the bed.
Crouching over the bitch's head she inserted herself into that hot moist mouth. Bending forward she and Chris kissed as they had so often dreamed of doing during their fantasy chats online. Their cocks spit-roasting the bitch between them, until the urge to ejaculate could no longer be resisted. They pulled out together and jerked until they both sprayed their sperm all over the prone whore, who now thought she had surely died and gone to pervert heaven. She had so long desired to be dominated and her reaction today seemed proof that she was a natural born submissive. So if that was the case, why fight nature? This is how she found herself easily embracing this lifestyle change that her son was offering her. Regardless of what happened next, Chris and his mom and dad would never see each other the same way ever again. For good or ill, the days of denial and repression were truly behind them now. All that remained to be seen was mom's reaction to her son's immodest proposal.