Simon began the following day with a stinging reminder of the prior night. It was everything and more than he’d ever imagined. He’d finally gotten the spanking he’d wished for as long as he could remember, but he wasn’t prepared for the intensity of the pleasure that such pain provided. Yes, it hurt, a lot toward the end, but the more it hurt, the better he seemed to like it. Remembering the frequent threats in the videos he loved of a spanking so hard, ‘You won’t sit for days!’ or maybe longer, he now saw them as idle threats. He loved the reminding sting and the memory of being over Miss’s knee getting a good, hard spanking. He hoped it would last all day.
Another lesson learned was that over-the-knee was not necessarily the best, the only position for him. He’d liked both impromptu spankings she’d given him, especially the one at the end. As with OTK, he liked the feeling of her arm wrapped around his waist, that time bent over and pulled to her side as she renewed the delicious sting with another hard, fast, and unexpected spanking.
There was one thing about the evening he wasn’t sure about. While he was more than willing to do anything she told him to, he didn’t quite like the belittling nature of her demands and scolding when he’d done something wrong. He was torn on this as he liked being told to serve her in any way she saw fit, but he didn’t like the way she jumped down his throat for every little thing. He’d prefer to be immediately punished for any failures on his part rather than made to feel like he was stupid or below her. He decided there wasn’t much he could do about it and accepted it as the price he’d have to pay for all the incredible pleasure she offered in exchange.
He’d be amazed to find how similar his feelings were to Monica’s. While she loved having Simon obey her every command, she had mixed feelings about diminishing him when he failed. She was over the moon about finally having a man accept the spanking she gave without question and had a strong suspicion that Simon would be able to handle, and like, a far more severe spanking if she built up to it correctly.
She’d been so set on defining him as a submissive in the BDSM sense she’d forgotten what she wanted. She’d used the sudden reprimands to provide the excuse for what she ultimately wanted to do: spank him. She rationalized that she hadn’t been sure what he wanted, was testing him at various times to find out, and felt she needed to establish her authority over him. ‘But would that be necessary any longer?’ she wondered.
She was sure that if she told him to strip and get over her knee seconds after walking in the door, he’d do so without question and quite willingly, but she hadn’t known that before. She was as new to this as he was and reminded herself that they’d need to learn this kink together. “Yes, together,” she’d said to herself aloud. Not her doing whatever the BDSM world expected of a so-called true Domme without regard for his desires. She finally concluded that it was her and Simon she had to please, and if that meant she wouldn’t earn her stripes as a dominatrix, then so be it.
Simon would, on his own, aim to please her in any way he could, but he also seemed to like being told what to do, especially with the consequences of failure. She’d decided long ago with other men that her vision of being ‘in charge’ didn’t include the more extreme activities, like tying them up or strapping them to a cross using whips and canes to beat them. The thought of water sports disgusted her, and she definitely didn’t want to put him or his cock in a cage.
She’d already told him he could stop her with a safeword if what she was asking was too much, and now, frankly, she couldn’t care less if that didn’t conform to the code of domination. She’d be quite happy, and she suspected Simon would too, to have someone who acknowledged her authority, put her pleasure first, and accepted the less extreme means of punishment, the spankings she’d give him when it suited her for whatever reason.
Having thought all this through, she found herself relieved to be meeting her expectations, not someone else’s. It left her in a position to decide what she’d keep from their first experience together, what to discard, and what to add to provide the escalation she knew they both wanted. She’d already identified before this revelation what she wanted to add and was pretty confident they would meet with Simon’s approval. Now, the only question was when.
Returning to work that day, they found it difficult to accept the self-imposed sanctions of work versus play. It was only last night, and neither could stop thinking about it, having each declared it a resounding success that exceeded their expectations.
As much as he didn’t want to, Simon told his boss that he could send someone else to handle Monica’s computer problems if he wanted. He didn’t want Eric to think something had happened or gone wrong with her, so he ensured he understood that either way was fine with him.
Sure enough, he took Simon’s suggestion and sent one of his colleagues to handle an install when she requested it, noting that Simon had no reaction to the assignment.
“Hello, Cindy,” Monica said when she arrived to do an upgrade on one of her apps. It saddened her a little not to see Simon, and she was a little surprised he’d carried through on his suggestion so quickly, but she knew it was probably for the best. She’d gone through the morning without calling the Help Desk, yet still hoped it would be Simon when she did, if only for one last time. With someone else doing his work, the question of ‘when’ was settled almost immediately. She wouldn’t wait long.
Simon had set up a unique alert tone on his phone for emails from Monica’s personal address, and when it went off minutes after Cindy would have arrived at her office, he feared she’d not be happy with the change. He opened the email with trepidation but smiled when he saw the message.
‘I want to see you on Saturday night. Same time!’
He responded with a simple ‘Yes, Miss!’ and you couldn’t wipe the smile off his face for the rest of the day.
Monica, too, was happier than she’d been in a very long time. It pleased her to realize that she not only looked forward to seeing his bare ass in her lap begging to be spanked but also having his expert tongue in her slit and his cock in her pussy, for which he had a talent beyond his years. All through the day, she found herself sneaking a quick stroke of her damp panties.
Saturday finally came, and after sleeping in for a while, she busied herself straightening up the house. This was going to be a little different than last time, and she needed to visit an adult store to get some new toys. She smiled at the realization that she was buying them to use on Simon rather than herself when she walked into her favorite store. She bought several items, but only a couple would be used that night. The rest were for future escalations.
She treated herself to a nice dinner at her favorite steakhouse, then returned home for the final preparations.
Simon needed to burn off the nervous energy that had been building since he got her message, so he went for a ride on the bike trail, pushing himself harder than ever. Over the last few days, he wondered what her statement, ‘It will get more exciting with time but more intense as well,’ would entail. He hoped that she’d use some implements when spanking him this time and wondered if the sex would get more intense in some way as well.
The night before, he’d gone shopping, hoping the stores would be less busy on a Friday night as he tried to fulfill her demand for sexier underwear. He’d pawed through the racks, not knowing what to look for, but was acutely embarrassed when a female employee offered to help. She had seen men like Simon before and knew how to gently guide them through various selections, offering her woman’s opinion on what would look sexy to her. He eventually accepted her advice and soon left the store, happy that he’d bought some that Miss would like.
Like last time, Simon arrived a bit early and tried to get his nerves settled before going in. He knew some of what would undoubtedly happen, and he couldn’t wait to be bare-assed across Miss’s lap getting spanked, hopefully even harder than last time. His nervous state was due only to what would be new and whether he could tolerate it. The penalty for failure didn’t worry him, but her disappointment would be worse; he wanted to please her so.
Monica had seen him arrive early as expected, and she completed her last preparation, putting a Post-It note on the door instructing him to ‘Come On In’ and stood in the middle of the foyer, hopefully stunning him with her appearance.
Unsuccessful at calming his mind or body, he finally got out of the car seconds before eight o’clock, ensuring he was on time. Climbing the steps to the door, he noticed it was slightly ajar, only seeing the small note when he stood directly in front of it. His anticipation ramped up a bit, hoping she had some kind of surprise just inside. He wasn’t disappointed.
“Oh my God, Miss!” he cried, standing stock still in the open doorway, trying to take in the vision. The Mona Lisa almost-smile on her gorgeous face, framed by her luxuriant long, straight hair, stunned him, but it was how she was dressed that tied his tongue. Red thigh-high stockings left only a few inches of dreamy thighs exposed, separated by matching red hipster panties that flowed between her legs seamlessly. Finally, the piece de resistance, a red satin corset laced up to her breasts with luscious cleavage, gave her the air of authority they both wanted her to exude.
“Oh my God, Miss,” he repeated. “I can’t believe how lucky I am to be allowed to give pleasure to someone so astonishingly and exquisitely beautiful!”
“Thank you, Simon. Come here,” she said, beaming with his finely worded praise and crooking her finger at him. “Don’t touch!” she added as she took his face in both hands, leaned in, and kissed him gently but passionately.
Letting go, she took his hand and led him into a large room with two seating areas in addition to a dining table. A wall of glass bordered the back wall, and he could see the remnants of a fiery sunset over the trees. They walked around a well-padded sofa with a high back and padded arms. He noticed an end table at one end but not the other, and the reason was soon revealed. It sat next to one of two armless upholstered chairs that matched the sofa, but it was what was on the table that captured his attention: a hairbrush!
“Would you pour us both a glass of wine, Simon?” she said, pointing to a coffee table with a silver tray underneath a bottle of Cabernet and two glasses.
He turned toward the table and poured the wine, and when he turned back around, Miss was seated in the chair closest to the misplaced end table. She accepted the glass from him and offered a toast.
“To us, Simon!”
“To you, Miss!” he replied, surprising her again with the just right phrase to exemplify his worship.
They each took a couple of sips, the alcohol already releasing some of the tension he’d felt on the way to her home. It had built further with her extraordinary display in the foyer, and now she was seated, making no attempt to hide the wet stain growing in her panties. If he hadn’t been with her here before, he would have sworn this was a dream.
“Do you like that, Simon? Hm?” she asked. Noting his stare at her crotch, she traced a finger down the dark line between the luscious lips apparent in her tight panties. Spreading her legs further allowed him to see the faint line grow in length and breadth. “Does it excite you to know it’s there because of you? Yeah, you make me wet, Simon!”
He felt like he could cum from that remark alone, but he wanted to finger, kiss and lick her pussy, not just look at it.
“Is this what you want?” she asked as though reading his mind and pulling the panties aside to reveal her glistening lips. “Not quite yet,” she said, using two fingers to pull the sodden strip back into position, her hand passing through her crotch several times and moaning loudly. “We’re going to play a little game first, okay?”
“Yes, Miss!”
“Last time, you had a little trouble following and challenging instructions. This game will help me see if you learned anything from last time. Do you remember the game ‘Simon Says,’”
“Yes, Miss!”
“Good!” she said as she stood a couple feet from him. She could see the arousal her close proximity created. “Simon says take your shoes off!” He bent to take them off with his hands. “Quickly, Simon! The game doesn’t work unless you do it quickly.” He stood and used his feet to peel the shoes off more quickly.
“Simon says, take your shirt off!”
“Simon says, pull your pants down!”
“Simon says, take your pants off!”
He followed her instructions as fast as he could, but each new demand came before he finished the one prior.
“Simon says, pull your underwear down!
“Pull your underwear back up!” she said and smiled when she’d caught him. “I didn’t say ‘Simon Says!’ Come here!” she scolded and pulled him by the wrist to bend him over at her side as she had done just before he left last time.
The spanks weren’t hard, but they weren’t soft either, and there were more than a few ‘Ows!’ mixed in with his groans of pleasure. A couple of dozen smacks on alternate cheeks, and it was over … for now. She stood him back up only inches away from her.
“Simon says, hold my breasts!” He smiled as he cupped them both from below.
“Simon says, kiss my breasts!”
“Simon says, kneel before me!”
“Simon says, kiss my pussy!”
“Lick my pussy!” she said and was quickly sighing as he made her wet spot larger, teasing her with his tongue on the bare skin adjacent to her panties as well. “Mmm, caught you again, Simon!”
He stood up, anticipating correctly another spanking, and was bent against her hip in seconds. She yanked his underwear down and spanked him similarly to the one before, the absence of protection ratcheting up the sting. She let him go and guided him to his prior kneeling position.
“Simon says, pull my panties down! Simon says, finger my pussy! Ohh, yeah!” she moaned and enjoyed his finger for a little longer, congratulating herself on catching him with each planned trap. “Mmm, Simon says, caress my ass with both hands!” She missed his long finger deep in her cunt, but she had another trap planned and squirmed a bit, enjoying his soft hands.
“Simon says spank me!” For the first time, he didn’t follow her instruction; instead, he removed his hands from her cheeks and looked up at her questioningly. “I said, Simon says spank me!” she repeated and felt his hands on her ass again. “C’mon, Simon! Spank me!” She jerked when he finally lifted each hand in turn and spanked their respective cheeks twice.
Grabbing his wrist, she pulled him up to stand before her, now realizing he’d been caught again, though in a different way this time. Expecting another spanking, he started to bend over, but she turned and walked away toward the end table.
“You haven’t done very well, Simon! Bend over the end of the sofa! I think we need to up the ante again!”
He assumed the position he’d wanted to try for so long and watched her with growing desire as he expected her to pick up the hairbrush and spank him in this new position. She reached for the table, teasing him by touching the hairbrush, but opened the drawer instead and withdrew two items he couldn’t see.
“Do you know what this is?” she asked, holding up a chrome butt plug and smiling when his eyes opened wide at something else that was new. “I see you do! Have you ever had one stuffed in that cute little butt of yours? Well,” she continued as he shook his head, “You’re going to now!”
She placed the plug on the sofa cushion before him and then revealed the other item: a bottle of lube. He’d liked having his anus teased and even shallowly penetrated, but the size of the plug, small though it was, had him worried, and it showed in his body language.
“Relax. I’ll take it easy,” she said as the flip-top popped open.
Not able to see what she was doing, the first thing he felt was drops of the cool fluid landing in his cleft and running down between his cheeks. She placed her finger just below the tight pucker, forming a dam that collected the slick liquid. Her finger slid up through his crack, twisting to coat her finger with it, and returned to his pucker to press gradually harder on it until the tip of her finger was in.
“Oh! Oh my God!” he cried softly.
She squirted some more lube above again and pulled her finger out to coat it more liberally this time before pressing in again almost to her second knuckle. Simon gasped as she fucked his tight hole, penetrating a little deeper each time until her finger disappeared.
“Oh, Miss! It … it … ohh!” he groaned as she finger-fucked his ass, slowly increasing the pace.
Deep gasping breaths accompanied her finger, now gliding easily in and out. As he got used to the feeling, he found he liked it, and instead of pulling away, uselessly trying to evade her finger, he lifted his hips to meet her thrusts, and the tight muscles slowly relaxed.
“Good boy!” she praised as she added even more lube, dropped the bottle on the floor, and grabbed the plug.
She could see him tense up again, so she continued with her finger, getting him to loosen up a little while rolling the plug in his crack to lube it up. She increased the pace with her finger until he relaxed a bit more, and upon pulling her finger out, she pressed the pointy end of the plug to his opening. Pushing slowly, the chrome tip went in, and probing a little deeper with each try, she gauged when it was time to press the wide part past his sphincter.
“Oh! Ohh! Ohhh!” he gasped as it forced him open, and then suddenly, “Oh God!” with a deflating exhale as it popped into position.
The full feeling was foreign to him, but he eventually came to enjoy it as well. She rhythmically pushed on the jeweled end, allowing him to feel it move inside him. She smiled at her success with another escalation she hadn’t been sure of. Without actually pulling it out, she tugged on it, alternately pressing on it again as he lifted his hips to push back against her hand.
“Mmm, excellent, Simon! You like it, don’t you?”
“Yes, Miss!” he replied enthusiastically.
“Maybe I should pull it out?” she teased.
“NO, Miss! Please? Not yet!”
She surprised him with another spanking, a bit harder than before, but he cried out when she grabbed his cock underneath and jerked him in time with the smacks. Realizing he would cum before Miss, he wondered about all the pleasure she was giving him and getting little in return.
“Oh, Miss! It feels so good! I’m gonna cum!” he warned. “Oh fuck!” he yelled as he made a mess on the hardwood floor, triggered by her tugging hard on the plug. Having slid back on the sofa’s arm to give her a better hold on him, it was now pressed hard against his chest, and he lifted a bit to allow freer breathing.
“Simon says stand up!” she said with a laugh.
He hadn’t fully recovered yet, so his chest was still heaving to get enough oxygen when he stood. Finally standing before her, his chest still heaving, he smiled and squirmed in place at the feeling of the plug in this new position.
“Please let me thank you properly!” he pled, not even bothering with just grateful words.
She took his hand and led him back to the chair, sat with spread legs, and rubbed her pussy as an invitation for him to take over. She smiled as he knelt before her and caressed her thighs, a little further up each time until they met in the middle. He pulled the soaking gusset away with both hands and leaned in to kiss and lick the very top of her thighs. He pulled the satin aside and teased her with a kiss and tempting lick from both sides. Moving his hands to the elastic waist, he waited for approval before going further.
“Take my panties off,” she said softly and added, “It’s okay. Game’s over,” when he waited for the proper instruction.
Her thoughts briefly went to her decision to do what she wanted and not worry about whether she was being dominant enough to satisfy someone else’s measure. She was still getting Simon to do her bidding, gratefully accepting his punishment, and now he’d lick her pussy all night if that’s what she wanted. The memory of his surprisingly talented and agile tongue in her slit had her pussy quivering.
Pulling on the waist, he drew them down as far as he could with her legs clamped on his waist. Lifting her legs straight up allowed him to pull them up and off her raised feet. Before she could put them down again, he put a hand on each thigh and pushed back until her pussy peeked out between her closed legs, and he leaned in to kiss and then lick her glistening lips, insinuating his tongue between them pressed tight together.
“Oh fuck! Oh, yeah, Simon! That’s good!” she cried as he licked and sucked the swollen lips in this new position for her.
She took over, holding her legs up, freeing his hands to join the fun. With his tongue slithering down over one hole, he teased the other, first with his tongue and then with a finger. Coated with her juice, it slid in easily to the first knuckle while his tongue returned to her pussy.
“Holy shit, Simon!” she cried when he lured her clit out of hiding and concentrated on it, his lips nibbling and tongue flicking.
He could tell she was near, but he wanted to prolong her cumming as long as possible, though she had other ideas. After pulling her legs back and apart, presenting her pussy like the sumptuous dessert it was, she took hold of his head and pulled it tightly against her crotch, grinding it against her spread lips.
“Ohhh, fuuuck!” she cried as she wiped up her milky nectar with his face, jerking each time his lips passed across her clit. Unable to hold her legs up any longer, they fell to the floor. She stroked his hair as he gently kissed her lips with a bit of tongue.
“Mmm, Simon! That was good! Really good!” she said between deep breaths.
She sat up when she could, with him still between her legs. She wrapped him in her arms and kissed him long and hard, her tongue getting involved near the end. Her hands had slid down his back to take his cheeks in hand, feeling only a slight warmth remaining, her fingers rediscovering the plug she’d forgotten about.
“Would you like me to warm them up for you again?” she asked with her hands caressing his slightly stinging bottom.
“Yes, Miss!” he answered with no doubt.
They stood, and she took his hand again, about to lead him to the bedroom, when he tugged on her arm to reach back and grab the hairbrush.
“Good idea!” she said, remembering they were learning this together, and regardless of their roles, they each had something to contribute.
–===<<<O>>>===–
Looks like they’re off to a great start with their ‘almost’ D/s relationship, but it’s about to get more serious! The continuation soon! Remember to ‘Like’ and/or ‘Favorite’ my story if you enjoyed it and … Thanks For Reading!!
