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Jason Chronicles #2 - Resuming My Lifestyle

"After a threesome D/s dinner, Samantha’s sister, Jill, has her turn with Jason."

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Author's Notes

"Soon after finishing Under the Rose my muse insisted on a sequel, so I wrote one from the viewpoint of one of the female characters in the previous story."

I was looking out an upstairs window when his car pulled up in front of the house. I’m really nervous, I thought to myself. Samantha told me what he said and did with her the other night on the plane and during their drive to my house, but she doesn’t know my ex and I were in the lifestyle while we were married. I never let on, never told my little sister anything about that, but we obviously share some submissive genes. Now this man is here, and I know he’s a Dom, and from what Sam told me he’s a knowledgeable and considerate one. But it’s been a long time since I played, over a year because of the period of separation and then the divorce with its emotional aftermath.

I turned and headed for the staircase, walking carefully in my new and very high heels. That’s another thing I haven’t done for a while, I reflected as I started down the steps. I used to wear stilettos all the time, and I really liked how they made me look and the admiring looks I attracted. My breasts bounced a bit as I descended, reminding me that I was dressed as he’d specified, without any undergarments. But they’re still perky, my C-cups, I told myself, still firm with only a little sag despite all the play they endured. The memories of those scenes, mostly good ones, flooded back into my brain, and I could feel a bit of moisture form in my pussy.

The doorbell rang as I reached the bottom of the stairs, but my sister got to the door first. She was dressed much as I was, both of us driven by his preferences for a button-front blouse, a knee-length pleated skirt, and our highest heels. She opened the door and invited him in; he was wearing a black suit with a deep red dress shirt open at the collar.

He took a couple of steps into the foyer and stopped; my sister closed the door behind him, walked around to face him, put her arms around him, and kissed him passionately. He put his arms around her in turn, held the kiss for perhaps twenty seconds, then released her.

“I haven’t been introduced to your sister, Samantha.”

“I’m sorry,” Sam said. “I was just happy to see you again. Please meet my sister, Gillian; she goes by Jill.”

The man took a step to the side so he had a clear view of me, then slowly looked me up and down before saying, “Hello, Jill, it’s a pleasure to meet you.”

“I’m happy to meet you also,” I said, “but I don’t know your name.”

“Samantha doesn’t know it either, but since I’ve spanked her and you invited me to spank you, for now both of you may address me as Sir.”

My heart skipped a beat when he said that. “Thank you, Sir, may I offer you a drink?”

“No, thank you, I’m taking you and Samantha out and we’ll have wine with dinner.” He held out his hand and made a come-here gesture; I walked to stand next to him, as Sam was, and I was pleased to find that he was three inches taller than I even in my five-inch heels. It had been a long time since I was with someone I knew was a dominant man, but I was always most comfortable when I had to look up to one.

*

He was, as Samantha had described and predicted, a complete gentleman, escorting us to his car, helping us get settled with me in front and Sam in the back seat, and driving to our destination, a popular steak house near my home. As we moved smoothly through the early-evening traffic he inquired how Samantha was enjoying her visit, and in response to his questions I told him I’d been living in my house for several years and it became solely mine in the divorce settlement. When we’d parked at the restaurant, he assisted us out of the car and offered an arm to each of us for the short walk inside. He gave his name to the hostess and we were led through the dining room to a table near the far wall, where Sam and I were seated across from each other. We looked over the menus and discussed the choices, and when the server arrived he ordered a red wine and we each stated our desires. But then he changed the game.

“From what I’ve seen, it appears that you are both right-handed. Each of you is to put your right hand under your thigh and keep it there.”

His assertion of control brought back old reflexes and I automatically complied without question, but I was unsurprised that Samantha objected. “How can we eat with only one hand?” she asked.

“Do you still trust me?” he asked in response.

“Yes, of course, but …”

“Then consider this just another new experience. You are free to disobey me, we have no commitment between us. But I hope you’ll go along for this new ride.”

Samantha blushed when she heard that; I knew she had vivid memories of the first ride she took with him. “Yes, Sir,” she said demurely, eyes downcast, and I saw her move her hand as I had done.

The wine was served, followed quickly by our first course. We started our meals with mixed salads, and the results were almost comical. Sam and I both giggled as bits of lettuce dropped back onto our plates; we weren’t accustomed to holding our left hands steady enough and our forks gyrated as we lifted them. When our entrees arrived, he reached over and cut the steaks into small pieces for each of us, and it turned out that the salad practice had been helpful. Our initial awkwardness gradually faded, and by the end of the meal we were almost casually putting our forks down to sip our wine between bites and feeding ourselves fairly adroitly.

On the drive home he asserted more control, fastening the safety belts of each of us as he had done with Samantha before their drive from the airport. He spent enough time securing her into the back seat that I was sure he was kissing her, and I silently debated with myself about overtly demonstrating my interest the way she had done. I definitely was interested in him, but I knew he was in a long-term relationship and I wondered whether just playing with him was the right thing for me to do at this stage of my post-divorce life.

When the moment of opportunity came, I chose to make my reawakening desires clear, and his immediate strong response took my breath away and made my juices flow. He held my hands in my lap with one of his, put his other hand behind my head, and kissed me intensely; I parted my legs and pulled his hand tight against the skirt over my damp pussy.

*

When we arrived back at my house, he turned in his seat and told Samantha, “When I release you, go in the house, go upstairs to the bedroom you’ve been using, and wait for me. I’m going to collect on my rain check, but I want a few minutes with Jill first. Do you understand my instructions? This is your chance to back out if you want to.”

“I understand, Sir, and I will comply,” she answered. He went around and opened her door, unlatched her belt, and offered her his hand. She took it, rose out of the car, stood on tiptoes to kiss him on the cheek, and strode to the front door, reaching into her purse for her key as she went. By the time she was inside, he was back in his driving position. The car started moving, and I knew what was coming.

“I watched your reactions earlier this evening, Jill, and of course I enjoyed your kiss. You don’t really want just a spanking and a quick orgasm, do you?”

“No, Sir, I want … no, I want and I need more than that.”

“Unlike your sister, you’ve been in the lifestyle, haven’t you? Was it with your ex-husband?”

“Yes, Sir, it was. But I’ve been away from it for over a year, what with the divorce and all, and I haven’t figured out how to get safely back into it, especially as a single person.”

“You know I’m in a long-term relationship, right? That’s not going to change.”

“Yes, Sir, I know, and I wouldn’t want to get in the way of that. But Sam told me you’re able to play with other people, and obviously you did with her and again a little with us earlier this evening. Like Samantha, I believe I trust you, and I’m hoping maybe you could help me ease my way back.”

“You want to ease back into the scene community, maybe find a long-term partner, but you don’t want to ease back into play, do you?”

“No, Sir, I think I’m ready to go in scenes. I know I’m ready mentally; the only question in my mind is how ready my body is for that kind of stress.”

“What does ready to go mean to you, Jill? Different people have different limits.”

“My ex-husband and I were fairly serious players with the floggers and other kinds of toys he used,” I told him, “and I was somewhat of a pain-slut. I may not be ready for quite as much at this moment, but I want to get back to that level of play as quickly as I can.”

“Okay, that tells me a lot about SM stuff,” he said, “and I suppose we’re negotiating now. What about other aspects of play?”

“I rule out the usual big squicks, scenes with children, animals, blood, and scat. Incidental cuts and enemas are okay, but nothing beyond that in those areas. Sexually, there’s probably nothing else I haven’t done, including the occasional threesome and more-some; the deeper I am into it, the more you can demand of me.”

“All right,” he said, “we’ll see how things go. But I want to reach closure with Samantha first, so you’ll have to wait until tomorrow for your first scene with me.”

“I understand, Sir,” I replied as he braked smoothly to a stop back at my house. “I’m anxious, and I’m eager, and I’m envious because I have a pretty good idea of how you’ll treat Samantha even though you’ll be gentle with her. But I know that withholding or delaying my pleasure is part of the head game, so go have fun with her, and I’ll be more than ready tomorrow evening.”

“Send her out to a movie or something,” he told me. “We’ll be making all kinds of sounds, and we don’t want to scare her out of her wits.”

*

The next day was Saturday, and it seemed to drag on forever. I spent hours wondering what toys he would bring and how he would use them. I alternated kinky fantasies with worries about what he might demand of me sexually and how I might respond, since I hadn’t had any sexual release from anything but my vibrator for many months. As the day wore on, I debated with myself endlessly over what I should wear to greet him, thinking that whatever I wore would probably come off soon after he arrived, except possibly my heels.

At five o’clock I ran a bath and soaked for twenty minutes. Then I drained the tub, turned on the shower, washed my hair, and shaved everywhere. As I dried my hair, I finally decided on a bustier top that laced up the back and a plain skirt; Sam pulled the laces tight, accentuating my waist and pushing my breasts up. We sat down for a light supper, and then she was gone, out for the evening. I slipped into my heels and sat on the edge of the living room couch, biting my lip and oscillating between nervousness and anticipation.

It seemed like a long wait, but only about ten minutes had gone by when the doorbell rang. Here we go, I thought, and I pushed myself up and went to the door. I opened it and said, “Good evening, Sir,” as I waved him in; he was wearing black jeans, a black polo, and deck shoes, and he was carrying a big duffel bag.

“Hello, Jill,” he replied. “You look terrific.”

“Thank you, Sir. Please follow me; I think you’ll want to see my basement.” Part of the legacy of my past lifestyle activities was a well-padded area rug on the floor, a pair of heavy-duty hooks set into the visible beam that crossed the middle of the basement ceiling, and a queen-size sofa-bed at the far end of the space that I had opened out and prepared earlier in the day. I led him to the doorway, flipped on the stairwell light, and preceded him down the stairs. When I got to the bottom, I hit the dimmer switch and turned the track lights down about halfway. He looked around and nodded in appreciation.

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“This will do fine,” he said. “I’d wondered what we might have available for a play space.” He set his duffel down, then reached into it and pulled out a two-foot-long one-inch dowel with eye bolts in the ends and two lengths of quarter-inch nylon rope. Then he used the ropes to suspend the bar between the eye bolts and the ceiling hooks and attached suspension cuffs to the bolts with quick-release snap-toggles. When he was done, the cuffs were at a good height for my hands and wrists; I could be put into them with my elbows comfortably bent. I’m impressed, I thought to myself; I’d hoped he really knows what he’s doing, and this sure looks promising.

“Step over here, Jill,” he commanded. I moved to stand under the bar and reached up to grab the cuffs’ built-in handles, and he wrapped the leather straps around my wrists and secured the buckles.

The soft fabric of my skirt glided gently with his hand movements as he caressed me, warming my bottom with the slight pressure of friction. I absorbed this gentle touch as he squeezed and stroked my behind through the skirt fabric, and the tingles deep inside my body reminded me how much I was anticipating this scene. His left arm circled to wrap me in a velvet vice, eliminating any freedom of movement, and then his right hand moved over my body. His fingertips traced feather-light touches over my peaks and valleys, exploring, feeling, testing for reactions, and I felt my inner muscles clench in response.

His hand flattened and his fingers spread and then closed to knead the taut muscles of first my right butt cheek and then the left, bringing a response of warmth as blood flowed to the manipulated areas and a shiver ran down my spine from neck to tail-bone. I tried to move, but I could only press against or lift slightly away from his thigh. Then he tucked the hem of my skirt into its waistband, and I knew what would happen next.

The first smack of his hand on my bare ass wasn’t all that strong, but my nerve endings, long unaccustomed to such impacts, awoke and my body lurched. My breath left my body in a grunt as his hand connected with a second smack. The sound seemed almost deafening in the quiet room as my fingers squeezed the handles and my muscles bunched in response to the sting of his slaps to my bottom. I waited anxiously when he paused, and then warmth coursed through the sweet spot where buttock meets thigh on my right leg. My body hadn’t shaken off its tremor from that lick when the next one landed with precision in the corresponding spot on my left cheek.

Smack! Smack! Smack! The sounds reverberated off the walls and bounced back, seeming as loud as firecrackers, as my bottom registered spank after spank from his hand. My feet danced, toes and stiletto heels alternately tapping against the carpet; my body tried unsuccessfully to twist into a position to avoid his expert aim, but his arm around my waist kept me firmly in place. The heat radiating from my behind made me hyper-aware of the area affected by the pops of his palm. His hand connected again and again as he switched from cheek to cheek, from high to low, sometimes diverting from my butt to swat my upper thighs.

My body writhed. My chest heaved when I inhaled and my breath rushed out in yelps and growls. I lost count of the endless series of smacks, my mind unable to think of anything but the heat I felt and the fluid flowing strongly from inside to out, tickling my lower lips and filling me with a sexual want so strong I quivered. My arms weakened from helping support my weight as my legs weakened from tensing and kicking, and my eyes brimmed with tears. The only movement of my body was the rhythmic thrusting and lifting of my pelvis as it pressed against his thigh and slid over his erection. The spanking wasn’t really that hard, but the heat rose on my ass and the sexual fire flared higher and hotter.

Then the spanks stopped, and there was no resistance when his hand pushed my legs further apart and his fingers stroked the silky wetness my body had created. The churning, gnawing, craving waves deep in my loins grew with his every touch. His left arm left my waist and my hips began swaying from side to side; my entire body proclaimed its desire in my movements and my inarticulate sounds.

He walked behind me, and the next sensation I felt was soft fur sliding over and soothing my well-warmed behind. That felt really nice, but after about thirty seconds he started alternating the fur with his bare hand, and that was even nicer. I had enjoyed the spanking, but in a way it was impersonal; the realization that he wanted to touch me again, that he wanted more intimate contact, increased the energy and strengthened the psychological connection between us. My hips continued their gentle swaying from side to side and I pressed my butt back against his hand.

“How do you feel?” he asked.

“Good,” I answered. “I feel very good.” He kept one hand moving on my behind and reached around to slip his other hand inside my top and cup my breast. The nipple was erect; when he flicked a finger back and forth over it, I felt a strong tingle in my loins. My hips jerked forward of their own volition, and I let out a long sigh. “That feels even better,” I whispered, and he smiled.

“I’m glad you’re enjoying this. I was hoping you would, of course, but after such a long absence from the scene I wasn’t sure how you’d react.”

“I wasn’t sure either, but I’m sure now that I’m ready for more.”

He made a slight bow. “I’m always happy to have such a beautiful and enthusiastic bottom.”

I felt myself blush. “Thank you for the compliments, Sir.”

“The first is well deserved, and the second is well earned. We’ll continue now.”

*

He walked behind me again, and when he returned to stand in front of me he held a rattan cane in his left hand that he started tapping against his right palm. This is going to hurt, I thought. The spanking was a strong warm-up, but this is the main event. I want it, but I’ve never been caned and I don’t know how much it will hurt. I hope it won’t be too much for this first scene; I really don’t want to have to say a safeword.

While I was thinking those thoughts, he walked slowly around me, still tapping the cane, sometimes into his palm, sometimes against his pants leg. After several circles, I felt the cane laid across my bottom, and I was instantly trapped between my concerns and my desires. I want this, I thought, I want this really bad. I hope he’s as good with a cane as he’s been with everything else so far.

The first gentle strike was followed by several more taps across my left and right cheeks. But then I sensed a quick movement, heard a hissing kind of whistling noise, and felt a new sensation: a sharp burning pain searing into the middle of my ass. I cried out, as much in surprise as in protest; the nature of the pain was new. It wasn’t flat and wide-spread like I’d known from other impact toys; it was a thin line that seemed more intense.

The second blow was just as fierce and it caused me to throw my head back. I wasn’t restrained other than by the cuffs overhead and my body flexed as my belly shot forward, instinctively trying to move my butt away from the target area. My arm muscles tensed, trying to pull me up, and I did a quick-step on my high heels, dancing more frantically than I had earlier. He walked around to face me and waited patiently while I calmed down.

“Are you okay?” he asked.

“I think so. It was different from anything I’d experienced before, and it’s been a long time since I’ve been beaten. You could say I’m out of practice, but now that I have some idea of what to expect I’m nowhere near ready to stop.”

“That’s good. Use your safewords if you need to.” He walked back around me, slowly tapping the cane against his leg again.

The third blow came, and then, harder, the fourth. I’m being caned, I thought, and I think I love it and hate it at the same time.

“You have some nice stripes now,” he said softly, and I felt a thrill. I’m being marked, I thought almost gaily. Except for a few bruises, that’s never really happened to me before.

A fifth stroke landed, and a sixth. I could hear myself moaning. It was pain, but it was also lust. I felt more alive than I’d ever imagined possible.

He was slowly increasing the force of the blows, and my butt, already sensitized from the spanking, was a mass of pain. I’d lost count, but finally my head hung down and I had reached my limit. “Please … no more …” I whispered.

“Two more,” he said firmly.

“No,” I started, “I don’t think I can take …”

“You can take two more,” he said. “Either your safeword or two more, and if you take those two I’ll let you come.”

When I heard that, I knew I had no choice. Despite the pain, I was so turned on the juices were running down the insides of my thighs.

Again there was that faint whistle and again I felt the fire searing into my ass. The moan that burst from my lips was a combination of pain and desire. I’d never known such pain, but I knew there was no escape from the final blow. I didn’t want that blow, but I knew just as surely that I did want it.

The whistle, the crashing pain in my rear end, and I knew the feeling of being utterly under the control of a man who could command me and manipulate and use me as if he owned me. My ex never brought me to this point, I realized, and I finally felt true surrender. Then the pain faded and my body relaxed as a sudden warmth suffused my entire being; I’d finally gotten the endorphin rush I’d heard and read so much about but never before experienced.

Then he spoke, and that dragged me up from my reverie. “It’s over,” he said from behind me. He slid his hand under the front of my skirt, gently pressed two fingers into my bare pussy, and slowly stroked my steaming tunnel. “It’s over, you made it, I’m very proud of you, and now you get your reward.”

He unfastened the cuffs, gathered me gently in his arms, and carried me to the bed. He carefully lowered me onto the bed on my stomach and lifted my hips. My knees tucked under me, lifting me to him as my head rested on the pillow. My hands gathered the soft coverlet, twisting it in tightly clenched fists as I felt him begin to probe for my entrance. I felt myself stretch to accommodate his hard shaft, and I heard his soft moan as he filled me, sinking deep and pressing against my tender behind.

My insides gripped his thick cock, and I couldn’t help but jerk as his finger touched my engorged clit. The simultaneous movement of his finger and his stiff hot cock, and the warm rubbing deep inside me, started a wave that consumed my thoughts. There was no thinking, only feeling, as his tempo increased, each of us thrusting to meet the other, helping each other find the fulfillment and release we both needed. Past the point of want, simply in need, we met, moving again and again, the rush gaining in height and intensity.

I felt the wave curling, breaking, beginning to crash in a strong orgasm that seized me, took my breath, and held me still for a moment before exploding and rocking my body in bucking movements. My climax surged through me; it went on and on. I felt him pounding into me, riding the wave with me until he groaned and spent his seed deep inside me. The room was filled with the sounds of gasping breaths as we panted and moaned in our mutual pleasure.

My body began to feel loose and limp as I felt his weight fall onto my back. His arms reached around me, his hands lifting my breasts out of their confinement and his fingers caressing them. I felt his heartbeat begin to slow, and I breathed deeply, sighing. I knew that for at least a few minutes we would feel totally at peace, sated and content, and the closeness we shared would be remembered for a long time. I also knew that I didn’t want this to be a one-time happening; we had connected too well to just walk out of each other’s lives.

    

Copyright © 2019 by Left Side Signals

Published 
Written by PatHarvey
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