She walked into the diner with no less than a hundred butterflies dancing in her stomach. The online flirtations between Jon and her had gone on for months now and they both anticipated this first face to face. Shay felt a kindred spirit in Jon. They shared many of the same thoughts and desires, and to top it all off, he was sexy as hell. It was completely unlike her to just jump in the car and drive the eight hours to Boston but she couldn’t fight her desires anymore. It wasn’t fair to her or to Jon.
They decided to meet in a public place at first, that way they could make small talk and become comfortable with each other before moving on to the more intimate items on their agenda. Shay looked around the cozy café, looking for a glimpse of the man who had intrigued her so with his written words. There he was, in the back corner booth, gazing out the window waiting for her arrival. He was even more stunning in person and her breath caught in her throat when he turned to meet her gaze. It was like an electric shock up her spine causing her to shudder with excitement.
He stood to meet her as she sauntered over to the table and embraced him in a friendly hug. It was funny, she thought, how at ease she felt with this man who, shortly, would have her in a very compromising position.
“I’m so glad you decided to come,” he told her with a winning smile.
“How could I not?” she asked. “You’re a hard man to resist.”
They sat and sipped their drinks and made idle chit chat. Jon asked about her drive up and Shay asked about his day. The innocent pleasantries soon gave way to the reason for this visit.
“So, young lady,” Jon began. “I think it’s about time we get you checked into your hotel and take care of some business.”
Shay thought it cute that he called her ‘young lady’ when she was a good three years his senior, but it also sent a shiver down her spine. This was finally going to happen! After so many conversations and fantasies, it was finally real!
“I think you’re right,” she agreed as they got up to leave.
They thought it best if Shay stayed in a hotel, he didn’t want her to feel uncomfortable at all so they kept everything very safe and low key… for now. She followed him to the hotel in her own car and was surprised and pleased when he came to open her car door and take her travel bag for her. He was as much a gentleman as she thought he would be and it put a smile on her face.
Shay got herself checked in and made sure they had a corner room on one of the upper floors for privacy’s sake. They got in the elevator and started the slow ride up to the top floor. As they stood alone in the elevator, Jon leaned over and told Shay exactly what she wanted to hear.
“As soon as we get in the room I want you to get yourself into the corner and think about what is going to happen to that behind of yours.”
She was trembling with excitement and was already starting to feel moist. She nodded her head at a loss for words. Jon playfully landed a smart smack on her backside and told her sternly “I expect a ‘yes sir’ when I tell you what to do. Is that understood?”
“Yes sir,” Shay whispered huskily.
The door opened and they walked the long hallway to the end and entered the room. Shay did as she was told and went to the far corner of the room and stood facing the right angle the two walls made. She was sorely tempted to peek behind her to see what Jon was up to, she heard him rustling around and moving things. Her curiosity could hold out no longer and she turned her head slightly to see what was happening.
“I didn’t tell you to turn around did I?” Jon said from directly behind her and landed another smack on her behind, harder than the last one in the elevator. Shay turned back around and said “no sir.”
She stood there, contemplating the fate of her bum for nearly fifteen minutes before Jon called her over. He sat in a straight backed chair in the middle of the room and motioned her over. She stood directly in front of him and he held her hands as he spoke.
“Now young lady,” he began, “we both know you’ve had this coming for a long time now. You’ve denied yourself something you desperately need and I know I am the man you need to give it to you. Your behavior, your self-destructive tendencies, your need to be in control… all of those things led you here today and I know, when we’re done here, you will be much happier. Now we’ve already discussed how you need a good discipline spanking and, believe me, you will get one, but I think we should start out slow and build our way up to it, okay?”
“Okay,” Shay agreed.
“Now I want you to come over to this side,” Jon pointed to his right, “and come over my lap.”
Everything felt almost surreal to Shay as she placed herself over this strong man’s knees.
He shifted so her feet were about an inch from the floor but her hands could touch the carpet beneath her.
“I’m going to give you a little bit of a warm up now,” he warned her before his hand landed sharply on her right cheek then on the left. He continued at a steady pace for a minute or two before he told her to stand up. He unbuttoned her jeans and pulled them down to mid-thigh and pulled her back over his lap again and resumed the spanking. SLAP, SLAP, SLAP, SLAP! The smacks were becoming harder and closer together and Shay’s bottom was slowly warming with a pleasant heat and a slight sting. She knew the whole spanking wouldn’t be as pleasantly warming as this warm up but the thought of Jon’s strong hand raining down on
her bare ass was enough to start the swarm of butterflies again. She felt herself getting wetter and she had to fight back the orgasm that was threatening to come.
After another couple of minutes Jon slipped his fingers in the waistband of her black silk panties and pulled them down to her jeans. The cool air rushing over her backside was exhilarating and the feel of his hand lightly rubbing her skin was even more so.
“That was your warm up,” he explained. “I’m now going to give you the real spanking
you’ve wanted your whole life. You can kick and cry out but I will not stop until I believe you’ve had enough. Is that understood?”
“Yes sir,” she obediently agreed.
SMACK, SMACK, SMACK, SMACK! Jon’s strong hand alternated from right cheek to left with perfect accuracy, reddening every inch of Shay’s round derrière. SMACK, SMACK!
He was spanking harder and harder, all the while lecturing her on not having to be in control all the time and letting herself give in to her desires. He lectured her about procrastination and even added a few words on speeding as she admitted to topping the speed limit on her drive up to meet him. Every minute over his lap felt like ten and she swore she was in that position for over an hour when he finally told her to stand up again. Much to her surprise she was only there for about fifteen minutes. Never before had she had a real spanking and it had been more than she had expected. The excitement she felt and the release he gave her was cathartic.
After she stood up, Jon brought her to sit on his lap and he held her close, ran his fingers through her hair and told her what a good girl she was for taking her first spanking of her adult life. He then kissed her cheek and told her to go back to the corner to think about what
As she stood there, bottom on fire, butterflies beating their wings to get out, she was struck with such a lustful desire she could have almost yelled out. She tried to convince herself on the ride up that she would behave herself and not let her libido take over for her, but now… being so close to this man that she was extremely attracted to, that she shared so many intimate feelings with, she wasn’t sure she could just let him leave for the night.
Jon called her out of the corner ten minutes later and asked her if she brought everything she was supposed to bring. She did. He told her to get the butt plug and some lube along with her new wooden hairbrush she picked up on the way there and bring them to him. She did as she was told, shuffling over to her bag on top of the dresser, moving clumsily as her jeans were still down around her thighs. He then pulled her back across his lap and told her he was going to put her plug in so she could focus on what was happening to her bottom and nothing
else. She was a bit nervous to have him probe into the most private areas of her body but she was so turned on the embarrassment seemed silly.
He playfully parted her cheeks and dabbed a little bit of lube onto her tight hole before he placed the tip and slowly pushed the butt plug in. He teased her by pushing it in then pulling it out, pushing it further then pulling it out. She imagined what his cock would feel like in her ass and almost came at once. She could feel his stiffening member against her side through his jeans and knew he wanted her as much as she wanted him, but oh, his self-control was amazing! She could only imagine what a passionate lover he would be. He finally pushed the
plug all the way in and she orgasmed then and there, quite unexpectedly. He must have been pleased because he chuckled and pushed lightly on the plug.
“You liked that didn’t you, you naughty girl,” he teased.
“Yes sir!” she panted as another wave hit her hard when he pushed on the plastic plug.
“Naughty girls get spanked with the hairbrush you know.”
“Do they?” she played along with him. This was quickly becoming a more playful and
erotic spanking. Neither of them complained.
“Oh they certainly do,” he said, emphasizing his point with two sharp smacks with the hairbrush, one on each cheek. The sting on her already reddening backside caught her by surprise and she jumped. “Ahh,” he teased, “a little more painful is it?”
“Just a tad,” she admitted through gritted teeth.
“Well then, let’s see if we can make it sting more than just a tad.”
He began to rapidly rain down smack after smack with that hard wooden brush causing Shay to squirm and squeal and breathe more heavily. It was no secret he was growing more turned on as she wriggled in his lap. He threw his right leg over both of hers to stop her kicking and held her more tightly with his left arm pulling her against his ever growing member. After a few minutes the spanks became slower and softer and Shay let her body relax as she felt more comfortable in his embrace. It was funny, she thought, that this man was causing her pain yet she wanted him, more than ever, to make passionate love to her. Trying to wordlessly convey her desires she lifted her ass a little higher and moaned deep in her throat. She lifted her hand from the floor and began lightly caressing his leg, being the only part of him she could reach.
Jon read her signals loud and clear and was more than willing to give her what she wanted. He placed the hairbrush on the bed and began rubbing her reddened and sore cheeks, every so often stopping to plant a light smack here or there. He purposely put pressure on the butt plug, still in place, as his fingers found their way to her glistening wet pussy. She was clean shaven, save for a small patch of hair at the crest of her lips, and he slid two fingers in easily. She could hear his breath as he quietly moaned above her and she arched her back inviting him to do more. He pulled her up and placed her on his lap again, looked at her longingly and gently pushed a stray strand of hair from her face to behind her ear. Jon’s hand lingered on her cheek before he pulled her face to his and kissed her sensually, deeply, passionately. Shay responded with deep kisses of her own, their tongues danced with each other, their lips married and parted then met again.
Jon lifted her in his arms as if she were nothing but a feather and gently laid her on the bed. He stood at her feet and slowly removed her clothes, stopping to kiss everywhere from her feet up to her neck, lingering over her ample breasts where he licked and sucked and playfully nipped at her nipples. While he trailed his kisses Shay was slowly undressing him, running her slender fingers over every part of his naked body she could reach. She wanted this to last yet she wanted him inside her now. Never before had she felt such conflicting emotions when it came to men and sex. This man with her now was different. She met someone of like mind and that could only lead to mind blowing sex.
Their naked bodies were now intertwined, pressed against each other, her soft body against his hard one… like yin and yang, they fit perfectly together.
“Are you sure you want to do this?” Jon panted, not wanting to stop but feeling the need to make sure before they reached the point of no return. Shay already felt they had passed that point and had no intention of turning back now, knowing she’d always regret it if she did.
“I’ve never wanted anything more,” she told him and wrapped her legs tightly around
him pulling him into her.
He slid in easily and they both gasped when he entered her. Months of flirting and playing out their fantasies, their eventual meeting was finally here. It was real, tangible and utterly incredible. Jon moved slowly at first, as if he was dancing to his own personal soundtrack in his mind. Shay responded by arching her back, thrusting her hips in time with his and moaning his name over and over. Her hands lightly caressed his back, his buttocks, his stomach and chest.
She reached up and kissed his neck and ears and face. He kissed her deeply and picked up his tempo. He whispered her name and groaned in pleasure as she tightened her grip on his waist with her legs. She pushed him to the side and easily rolled on top of him, swapping places with him. Now he was at her mercy.
She sat upright, straddling his hips, his pulsating cock still deep inside her. Jon looked up at her and let his hands trail from her neck to her breasts down to her hips. Shay began slowly riding him, lifting her body until only the head of his dick was in her wet pussy, then she’d slide back down his shaft. Over and over she teased and taunted him with her slow lovemaking, driving him crazy. Just when he thought he couldn’t take any more she quickened her pace. Her hands gripped at his strong chest and she thrust her hips faster and faster, tightening that muscle within her so it felt like a strong fist wrapped around his cock. They were both so close to orgasm they could feel it happening at once.
“Oh God!” they both muttered out over and over again.
With one final thrust time stood still. Up was down, left was right, right was wrong. They exploded in the most intense climax either of them had ever felt before. Shay collapsed onto Jon’s chest. They both breathed heavily. He lifted his hands to lightly caress her back, up and down his fingers trailed leaving goose bumps in their wake. Shay covered his bare chest with light kisses as she lay in his arms.
Finally, having caught their breath, Shay rolled off of him and curled up next to him, her head resting on his shoulder. They let their fingers discover each other without really paying attention. Jon’s hand found itself in Shay’s hair and he played lazily with her blonde tresses. Shay drew nonsensical patterns on his chest with her fingers, occasionally trailing them down his stomach to lightly play with his still stiff member, sending shivers up his body.
“Wow,” was all either of them could say.
They dozed lightly, never really falling asleep and came out of their daze some time later when Jon rolled over and propped himself up on top of her again. He looked at Shay longingly and kissed her deeply as he slid back into her wet warmth again.
“Ever think a spanking could lead to such passionate sex?” he asked her.
“Only in my fantasies,” Shay admitted.
“Roll over,” he commanded her and she did as she was told. “I see you still have your plug in.”
Shay had honestly forgotten all about the butt plug in her ass.
“I think we can take that out now.”
He slowly removed the rubber device and tossed it aside. He lifted her hips up to him and she felt his cock press against her tight ass. She had told him before she’d like him to fuck her in the ass and, oh God, he remembered.
“Tell me what you want Shay.”
The butterflies were back again full force. She was still more aroused than she had ever been in her life and when his hand fell on her bottom to get a response out of her she arched her back in intense pleasure.
“Tell me what you want me to do to you Shay,” he insisted again.
“I want you to fuck me in the ass,” she told him.
“Good girl,” he said as he slowly slid all the way into her tight hole.
The feeling was so intense and he felt so good inside her she never wanted to stop. He thrust slowly and deep, relishing in every moan Shay made.
“Good God Jon, don’t stop!” she panted.
Jon was more than willing to oblige. He quickened his tempo, grabbed hold of her hips and slid as deep as he could go. Faster and harder until they were both moaning and gasping for air and calling for God and each other and any other nonsense that happened to spill from their mouths in the moment of intense passion. He came deep in her ass with one last thrust and they collapsed to the bed, thoroughly exhausted and completely sated… for now anyway.
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