Hard Luck Harry’s First Play Party

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tagFirst TimeHard Luck Harry's First Play Party

This is a work of fiction but my muse, Mistress Ila May, is very real and this fantasy was written with Her permission.
Although Harry was over a decade older, Mistress Ila May was the one teaching him the ways of the flesh. Harry wasn't a virgin, but his experiences had been very limited in scope. Mistress Ila May, still in her twenties, had lived quite a life already. Harry needed a mentor and Mistress Ila liked the idea of molding a pet into a custom made plaything. The story today is just one of hopefully many:
Harry drove his car through the gate. It would be an understatement to say that he was nervous, but he trusted Mistress Ila May. Although she was the dominant member of their dynamic, tonight she would allow him to be dominant as this was part of his training.
The house was magnificent! The hosts for this evening were obviously very well off. Harry felt outclassed, but his companion boosted his self esteem more than enough to make up for it. He knew she was out of his league yet here she was, with HIM.
Mistress Ila also knew he was beneath her station, but there was something different about Harry. She didn't understand it completely, but she knew that he filled a gap in her life. She had other lovers, better lovers even, but they weren't Harry. They didn't make her feel the way that Harry did.
Stepping out of the car, Harry walked around the vehicle to let Mistress Ila out. The theme for the occasion was School Daze. Harry wasn't sure what look exclusively said "teacher" so he opted for slacks and a cardigan over his dress shirt paired with some costume bi-focals. Mistress Ila was dressed like a slutty school girl. Her see-through-white button down shirt at least one size too small and her plaid skirt almost covering her ass. Knee high socks and a high ponytail completed her look.
Harry flashed a nervous grin while Mistress Ila May gave him a reassuring smile. He took out a red collar with a geometric star pattern that shimmered in the light and clasped it around her neck. He held up the leash. She was now officially His plaything for the evening.
Harry led Ila towards the door with a gentle tug. She obediently followed, the leash making sure she didn't fall behind. Harry handed the doorman the invite, the beautiful woman under his command bolstering his confidence. The door was opened and they entered.
There was a TAURI+ReAX Temperature-Check Tablet on the wall in the entryway. They each took turns having their body temps scanned. After passing, they were allowed into the main part of the house. Harry mused, "Group sex in the time of Covid."
The interior resembled more of a museum then the setting for a sex party. They walked through the home towards a cluster of people. As expected there were school girls, cheerleaders, jocks in jerseys, schoolmarms and even what looked like a gym coach. As Harry and Ila walked in Harry caught a few knowing glances aimed at the woman on his leash. This was her crowd and there was no doubt that some of the other patrons knew her intimately. Ila, for her part, did not show any reaction at all. This wasn't her first rodeo.
While Harry half expected to walk into a sea of naked bodies he was relieved that the true party hadn't started yet. He grabbed a couple glasses of wine for himself and Ila. He may be the one in charge this evening, but he was still a gentleman. Since Harry was a stranger in a strange land his anxieties did bubble to the surface. He felt that this would be a good time for Ila to chime in. Harry leaned back and whispered in her ear, "You have permission to speak freely," and it was like a spark was ignited. She instantly set about making introductions and catching up with old friends.
Harry was in awe of her. She was amazing. Truly someone special and he knew it. He'd only known her for a few months but he felt more calm in her presence. She allowed him to blossom.
Ila introduced Harry to a couple women dressed as school girls, Laura and Sara. Their outfits matched each other, but Laura had the cutest face with smokey eyes and a shaggy mane of dark hair that perfectly suited her curvy body whereas Sara was a skinny blonde with piercing blue eyes and an aquiline nose.
And there was Robert and Susan as a jock and cheerleader duo. Robert was far too lanky to be a football player and Susan's buzzcut would be very out of place on most cheerleading squads but you almost got the feeling that that was the point, like it was an inside joke just for them.
There were others Ila knew to a degree as well, sometimes only as faint memories of intertwined limbs. Ila tried to remember who all she had sucked, fucked or broken their hearts and that task started to feel like a fools errand.
After catching up and making small talk the conversation shifted to what everyone was here for. Laura and Sara were hoping to find a new girl to prey on, and Robert and Susan had tentative plans for a full swap with a couple they'd met at a previous party.
Ila explained that Harry was new to the Lifestyle and that she was acting as something of a mentor to him. What she didn't say out loud was that it was also a test. Harry had seen her with other men on her Only Fans page, but how would he react to it in person? She'd had enough relationships fail because men wanted to possess her and contain her sexuality. Deep inside she knew that no one man, or woman, could satisfy all her needs. Not sexually, not emotionally, and certainly not spiritually.
The hosts soon appeared. They were an attractive couple, probably in their early 40s. He looked like a college professor in a crisp suit accessorized with a calabash pipe. She wore a long grey skirt and a blouse that could've been called frumpy if it wasn't for how tightly it wrapped around her breasts. Her hair in a tight bun gave her a sinister look as did the ruler she was lightly smacking on her open palm.
They went over the house guidlines; recommending moderate alcohol consumption, encouraging the use of the free condoms and wet wipes stationed around the play areas and reminding everyone to keep it safe, sane and consensual.
At this point Harry knows it's on. With a glance, he lets Ila know it's time to resume her docile position. She shuts up and he starts to parade her around. He had considered making her crawl around on all fours, but ultimately he decided against it as it seemed to be a touch much.
Harry had an air about him that was unfamiliar to him. He wished that he could feel this way all the time. With Ila by his side, he just might.
Harry sees Rpbert and Susan flirting with another couple that he hadn't seen earlier. Both men still with their significant others, but looking eagerly at the women across from each other.
Laura and Sara have taken up residence on either side of a young blonde with a Greek lettered sweatshirt as her boyfriend grins like a fool. She looks young enough that Harry wonders if she's still in college. Is that sweatshirt authentic?
Harry and Ila discussed earlier what they each wanted to get out of this night. For Harry, he really just wanted to experience something new although he was kind of hoping they could add another girl to the mix. If possible anyway.
For Ila, she had told him that she wanted to be given away freely. Harry didn't realize this was also a test for him, but he adored Ila and he would do anything to please her. If she wanted to be gifted away, so be it, Ila gets what she wants. Ila ALWAYS gets what she wants. Harry makes sure of it.
Harry walked Ila over to a group of people who were still chatting and taking in the sights. This group included the Host and Hostess, a goth cheerleader and jock couple and a girl dressed in a sexy Hogwarts uniform.
"Excuse me," interrupted Harry, "this is my companion, Ila. She will be made available for play later this evening, but you're more than welcome to sample her now if you'd like."
Hogwarts girl smiled and approached Ila. She was a very leggy brunette with a hint of red in her hair. Looking at Harry, "One sample, please." She petted the side of Ila's face a couple times, softly. She wet her lips, as did Ila. Then she leaned down, tilting her head, bringing her lips slowly to Ila. Their lips locked in a magnetic first kiss.
It made Ila float backwards ever so slightly. Hogwarts responded by pulling Ila tighter. Her lips opened to allow Ila's tongue to run along her lips and slip inside of her mouth. Their tongues met as they shared the passionate kiss. Hogwart's tongue danced with Ila's, slipping by to lightly trace the other woman's lips. The kiss grew deeper and deeper as Hogwarts gave into her passions and the tongue of her new friend.
Ila ran her tongue along Hogwart's lips one last time before lifting her head up and looking at the smiling face of Harry. She could tell he was pleased, and her sub side felt pleased as well. As a true switch she reveled in pleasing her Sir, even if she would be the one beating His ass the next weekend.
Hogwarts gave Ila a once over. Looking her up and down one last time, "Maybe I'll see you later," then she walked away to watch another scene unfold.
The hostess watched as the brunette disappeared, staring lustfully at her legs. After a moment of reflection she turned her attention to Ila. She examined her visually. Looking her over from top to bottom, front and back, she finally spoke. "Does IT enjoy pain?" she asked Harry, her eyes never leaving Ila. Harry responded, perhaps too enthusiastically, "Oh yes! Very much so!" He regretted sounding like an over excited child. How would he earn respect if he couldn't control his emotions better.
"Gooood… Samantha, undo this, THINGS, buttons" she said to the goth cheerleader, motioning with the ruler.
Samantha was doing her damndest not to smile, but as she approached, Ila noticed a quiver in her lips that betrayed her. Samantha reached out, her fingers pulling one side of the shirt ever so slightly to her left while her other hand pulled the other side out to allow the button to slip out through the buttonhole. And then the next, and then the next, and so on until the shirt was left hanging open.
The Hostess used the ruler to move each side of the hanging shirt to the outside of Ila's bare breasts. She next used the ruler to lightly spank her left nipple. Then with gaining intensity, and then finally with a loud snap!
Ila gasped, almost squeaking as she attempted to contain herself and show this hostess just what she was made of.
Changing gears, the hostess gently grazed Ila's right breast with her fingernails. Next she caressed the bottom of the breast with the palm of her hand, up and brushing past the nipple. Using her fingertips she then softly pinched the nipple, slowly rolling it around. She lightly pulled it away from Ila's body before letting go and watching it bounce with freedom.
The hostess had one more test. Using her head she looked at Samantha and motioned to the exposed right tit. Samantha leaned down and began licking and sucking the nip. All the sensitive nerve cells firing, it was a beautiful if not intense feeling. Ila was almost lost until she started feeling a growing pain from her other teat. The Hostess was using her sharpened nails to pinch the left nipple with enough force that Ila thought she was trying to draw blood, though she never did. The mix of the two sensations was overwhelming. She would've probably had a wet spot showing on her panties if she was wearing any.
Out of nowhere came a hard smack against her ass! Who did that?
It was the man that Harry had noticed earlier, dressed as a PE Teacher. Ila's mouth hung open; she had not seen him before but she was seeing him now! This was a Man with a capital "M". He was at least 6 and a half feet tall with thick brawny muscles and dark hair covering his arms and chest. Ruggedly handsome with a charming smile and eyes that flashed both Heaven and Hell. Ila wasn't a religious woman but she prayed that he had a cock as magnificent as the rest of him.
The Hostess and her minion took a step back. This wasn't their playtime anymore.
Ila instinctually bent over as he was groping her ass, all the while keeping her eyes on this mountain of a man. He spoke for the first time, his voice a commanding presence, "I heard something about a sample."
His meaty fingers traced the crease of Ila's lips, as his thumb gently placed pressure on her asshole. He refused to put his fingers in her though, taking his time teasing her. From the feel of things Ila was certain that his fingers were bigger then some of the dicks she had taken.
She was desperate for release. Her mouth still hanging open, her eyes wide, She began slowly rocking her body back and forth matching the rhythm of his fingers. He wasn't going to let her have the satisfaction. At least not yet. With supreme confidence he stated, as a fact, "I WILL see you later," before walking away.
This had Harry worried. With men like that in the world, what would any woman, let alone a woman like Mistress Ila, need him for. Still, he knew that if nothing else he had to save face, but he had to do so carefully. If his jealousy was too obvious then she would have reason to leave him behind. Besides, he reminded himself, he wanted to make sure that she was satisfied tonight and he knew that Man could most certainly satisfy her.
"Does my pet see anyone she likes?" Harry asked Ila. She paused for a second, not wanting to seem too eager. "Maybe," she sighed.
The Hostess smirked in such a way that Harry felt like he was on the outside of an inside joke. She walked away with the goth couple following her.
* * * * * * * * * * * * * * * * * * * * * * * * * * * * *
Harry allowed Ila to be sampled by a few others. Making out with a couple here, a few teasing partial blow jobs there… Laura even took some time away from Sara and their new friend to finger fuck Ila and feed Ila her own juices, but nothing turned her on like the gym coach had.
Ila had made her choice, but she needed Harry's permission to act on it. Her body ached with desire. She wanted to fuck the gym coach. She needed him to fuck her.
She needn't say a word though. Harry weighed his options. Hogwarts would be fun to watch Ila with, The Hostess probably had some nasty tricks up her sleeve, Coach would be very pleasing to Ila though. And as her Dom for the evening wasn't it his responsibility to nurture her needs?
Harry was still scared to say the least. He had seen her with other men, sure, but not like this man. Even though Ila was very poly, Harry was still learning about open relationships and still had a lot to learn. He hadn't felt this kind of jealosy for at least two decades, but just like Cassy before, he knew that he'd help Ila get her man. Harry just hoped that it didn't break him like it did last time.
To maintain her submissive state, Ila aimed her eyes at the ground as Harry lead her by the leash. Finding Him in the lounge, Harry locked eyes. "Sir? I would like to offer you the gift of my date. Do you except?"
"That depends," his voice echoing in Ila's soul, "What do you need from me in return?"
"Nothing really. I only ask that you use her in the open so everyone can enjoy the show, and that you treat her well as I will be needing her later," Harry stated plainly, "and yes, condoms are required."
It felt so powerful to be able to do that. He had always assumed that he'd feel like a cuck, but instead he felt supreme. He decided who she fucked, and who she didn't fuck.
Harry removed the collar from Ila's neck, he then placed her hand in the giant mit of the man before them. Ila was now his until he was done with her.
Coach led Ila to a velvet red sofa. He then placed her down into the seat. The material felt impossibly soft on her bare ass. His hulking body above her, he removed his shirt. His hard earned muscles covered by a thick mat of dark hair. He looked her deep in the eyes, my God his eyes! They burned with passion as he slowly lowered his mouth to her neck. His kisses were tender yet intense. Commanding but with a hint of need.
Ila was lost in the sensation, but she also felt a longing wrapped in sadness and pure affection. It wasn't coming from the beast of a man working his way down her chest though. She opened her eyes! Standing with eyes that bored into her heart was Harry.
Ila had seen that look before but she didn't see it often. In fact, she almost didn't recognize it. It was love. Harry was showing Ila that he loved her with his eyes as she was about to be ravaged by a man that Harry could never be.
This turned her on more than she ever would've imagined. Coach was gently kissing her pussy, one giant finger probing inside while Harry shared his heart without saying a word. And there was also lust. Harry wasn't just allowing her to fuck this stranger, he needed to see her fuck him. His eyes so full of love also told her she was a fuck toy to be used. Oh, how she wanted to be used.
Ila almost felt like she was in two places at once. She felt the physical presence of the man licking her open pussy with a rough tongue and the spiritual presence of the man she came with.
Harry somehow felt everything Ila felt, their beings intertwined like quantum entangled particles. Their eyes were locked on each other.
Coach stood up on his knees in front of the sofa as he undid his shorts. His massive member at the ready.
He reached into his gym bag (because of course he had a gym bag) and grabbed a condom. These parties didn't usually have condoms large enough for him so he'd gotten used to bringing his own.
After rolling the condom on, he rubbed the head of his cock against Ila's waiting cunny. She was positively dripping. She just needed to open a little further to fit it in.
Ila, with her eyes still locked onto Harry's, felt the head push past and into her canal. She let out a gasp! It was SO thick! He pulled it back before pushing it in further. Ila gasped again, but for a split second she was fucking Harry in her mind.
Coach kept slowly sliding in and out, each stroke a little deeper. Ila felt every square inch of her pussy filled, but she never lost sight of Harry's eyes. As Coach started to pick up speed, Ila matched his rhythm, her breathing perfectly timed.
Thrust! Thrust! Thrust! Eyes on Harry. Gasp! Gasp! Gasp! Her spirit in sync with Harry across the room.
Coach pulled her off the sofa as he leaned back, his perfectly sculpted ass resting on his feet. He brought her body into contact with his, holding her tight, never stopping his thrusting. Ila wondered if she was taking all of his cock, or was there more? She wasn't sure if she could take anymore of him anyway.
Harry didn't want to appear to be turned on but it was obvious by looking at his pants just how hard he was. Harry wished he could just start jerking off, he wanted to come so badly, but even in this setting it didn't seem appropriate.
Coach moved his hands from Ila's hips and gripped her ass cheeks tightly. You could actually hear how drenched Ila was. The "squelching" noise almost echoing throughout the room. Ila's head resting on his shoulder, making love with Harry's eyes.
With one hand holding Ila in place, the other reached in his bag and found a bottle of lube. He poured a liberal amount on his fingers. Then Coach spread her cheeks and pressed his right index finger deep in her ass. Sometimes his finger moved in at the same time as his cock, sometimes he alternated. She started to grunt.
Ila wanted to close her eyes and focus on the physical sensations traveling through her body, but she kept her eyes on Harry. She was so close to cumming, but she couldn't; not without Harry's permission.
Ila was riding the wave but never succumbing to it. She was almost to the point of begging Harry for permission to cum when she felt coach pull out. She almost panicked at the thought of being denied.

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