If you would like more insight on Jen and I, please feel free to read these.

Office Encounter Part 1

Office Encounter Part 2

The hard packed snow crunched under my boots as I shuffled up the frozen sidewalk toward Jennifer's home. Jen's house was large, but was quite a ways out of town in a small rural neighborhood. She had bought it long ago, just after her divorce. She had always talked about her home being much bigger than she needed. Deep down I felt that she probably had intended on filling it with a family, but she was past that part of her life now. Jen mostly lived on her own, but sometimes rented out her spare rooms to friends over the years. In fact, just before her and I started working together, she had rented a room to a mutual colleague, Natalie, that worked on the floor below ours. Natalie was a close girlfriend of Jen's, and I had worked with her in the past as well, so it had posed a bit of a complication initially. The good news was that Natalie was often gone on the weekends; specifically this particular Saturday afternoon.

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Even still, I chose to park a little way down the street as Jen and I were very new into our relationship. Jen and I had agreed that we didn't want anything getting back to Natalie from the nearby neighbors for the first few months of our relationship. We mainly did not want our employer to know that we were dating. Obviously, we did not want to be reassigned to other departments or fired... especially considering our office escapades earlier in the week. All this ran through my brain as I reached Jen's front yard. The icy wind whipped and bit the back of my neck and ears, snapping me out of it, practically pushing me to her front door. I had only been there once before, but it had been dark out. In the broad daylight, even covered in snow, I could tell her front yard was nicely landscaped and the house was well maintained.

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I knocked politely at the door. I held a bottle of gin in one hand, and a bag of groceries, to make a late lunch with, in the other. My weekend bag was slung over my shoulder. After a couple seconds, Jennifer opened one of the tall double doors. She quickly pecked me on the cheek, ushering me in out of the freezing cold. As she shut the door behind me, I set my weekend bag down at the base of the stairwell along with the gin. Before I could even say hello or how bad the roads had been driving over, Jennifer had wrapped me in her arms and planted a loving but sensual kiss on my lips. I could tell immediately that she was already in the mood. Her long, blonde hair was up in a very high bun and her makeup was flawless. She had a white loungewear-style robe on, and what appeared to be a loose fitting pink t-shirt and matching lounge pants on underneath. As our initial embrace ended, I turned to put the groceries in her refrigerator.

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"I got that babe. Are you hungry yet? Or did you want a drink first?" Jen asked sweetly, taking the bag from me.

"No, I am ok for a bit, so actually a drink sounds perfect!" I replied.

"Why don't you go set your stuff upstairs in my room while I put the food away and mix us a drink?" Jen suggested. "I left you something comfy to wear on my bed. I turned heater up, so it should be pretty warm upstairs. I'll meet you up there."

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I kicked off my boots and jacket by the front door before heading up the stairs into the spacious master suite. Jen's bedroom was in the front of the home and the large bay windows looked out over the local mountains in the distance. Even though it was the first clear day we had experienced in a while, the mountain tops were engulfed in clouds. I looked at the bed. On her large grey comforter sat a matching pair of black silk lounge pants and shirt. There was a pair of black silk boxers to go with them. I set my overnight bag down by her dresser and began to pull off my clothes, folding them neatly as I did. I slipped into the boxers and loungewear, noting how soft they were. There was a small fire burning in the fireplace, so I stoked the flames and added some more wood. As I did, Jen came into the room.

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"Is it warm enough in here for you?" she asked me.

"Yes, its excellent." I answered. Jen handed me a fresh gin and tonic. We clinked glasses and I tasted that familiar flavor on my breath. Jen smiled at me and leaned in for a kiss. It was not until that moment that I realized that Jen was no longer wearing the pink loungewear under her white robe. I also noticed that she was taller than when we had kissed downstairs. I took a step back.

"Do you like them?" Jen asked coyly, looking down at the sleek, tall, black heels she now wore. I hadn't heard them click with her footsteps as the entire upstairs was carpeted and muffled the sound.

"I love them," I replied.

"What about this?" Jen asked taking a step back and untying the belt on her white robe.

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Jennifer opened the robe quickly and let it fall to the floor. She wore a complete set of high-end, black, bondage-style lingerie. Her bra was mostly see through, her pale skin sparkling through the black lace. Below was a black thong with a gold zipper down the front of it and both high and low waist straps filled with gold rings and clips. She topped off the set with fishnet stockings and the shiny black heels. I stood there in awe of her. She did a slow spin around to give me the full effect. Her perfect, plump ass was barely contained in the tapestry of the thong's waist straps. The thong had no back to it at all, aside from the gold rings and black straps that converged to a single, larger gold ring at the small of her back. As she spun, she bent over slightly, revealing her tight pink asshole and just a peek at her pussy lips covered mostly by the bottom part of the thong. I felt myself growing in the black silk boxers, wondering if my pre-cum had already stained the inside.

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When Jen had completed her 360 degree fashion show, she stopped and smiled at me. Without a word she walked over to the bed and motioned for me to follow. She took me by the hand and we pulled down the big grey comforter. I gasped. Underneath that warm comforter, the white bed sheets were lined and covered with white towels. Only the pillows at the head of the bed remained exposed. That, however, was not why I gasped. I gasped because in the center of those white towels, laid out in a perfect row, were Jen's sex toys. She had it all; vibrators, a magic wand, nipple clamps, ties, a riding crop, cuffs, and even a few glass dildos. Up until that point in my life, I had only encountered a few toys. A couple of my past girlfriends and flings had vibrators or small toys here and there, but I rarely played with them. I also had only a few minor bondage and dom/sub experiences as well. This was all fairly new territory for me.

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"You know how I told you that I can cum over and over without ever stopping?" Jen started, "Well this will be our first time without the constraints of our office. At some point, I am going to need you to be the responsible one and end the session. Can I trust you to know when to stop?"

"Of course. I would never hurt you Jen," I replied in understanding.

"Oh, I didn't say that... Just know when to stop. Speaking of, have you ever been a dom before?" Jen asked, reaching for the cuffs on her bed. I realized as she began to apply them to her wrists that they matched her gold and black strappy thong.

"No, not really." I answered.

"Well, Daddy, you're in charge starting now," Jen said in a submissive but sly tone, "Oh and can I offer you a piece of advice? Unless I say the safe word we talked about, do whatever you want to me."

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I stood there for a moment in shock. This 37 year old woman, this cougar that I adored, this woman who I looked up to, had literally handed me all of the power in the room. I was 10 years her junior and she went from being this feisty, fiery older woman, into my submissive slut in less than an instant. My eyes searched for answers deep within her soft sparking blue ones. Jen saw my inexperience and winked at me to boost my confidence, then resumed the puppy dog eyes. As I looked Jen over from head to toe, deciding how to start, I realized that even in her submissive state, her lingerie and heels exuded power. I knew in that instant that I needed to remove that power, or at the very least, punish her for having it. So like a young artist applying the first strokes of paint to a blank canvas, I began to work. I knew that this was all new to me, so I started with what I was familiar with.

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I walked up to Jen, pinning her between myself and the bed and embraced her in a firm grip around her waist. I moved in to kiss her and our lips met in an explosion of passion. Just the thought of being dominated by me, a younger man had already started her engine. We kissed hard, our tongues wrapping and contorting, our saliva mixing. As Jen moved her hand up the small of my back to embrace the back of my neck, I caught it with a firm grasp. Pulling her hand down to her side, I held Jen tightly and clipped the wrist cuff to one of the many gold rings on the side of her thong. I think Jen was surprised by how quickly I had transformed and how firmly I had grabbed her that the kissing stopped for a moment... but only for a moment. She tried to use her free hand to feel my cock through the lounge pants and boxers. I let her get the slightest touch then secured that hand to her other side. Jen's arms were completely restrained at this point. I reached down between her legs and felt that her thong was already soaked with excitement. She wanted me.

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I took a step back, leaving her mid-kiss, standing against the edge of the bed. I walked over to where I had set down my gin and tonic, and took a sip, all while deciding where to start. Jen moaned and begged me to come back, but stayed obediently in her spot. One of her nipples was starting to peek over the top of her lacey bra, probably from how roughly I had restrained her. My mind flashed back to the office. I had it. Walking back over to the bed, I reached for the nipple clamps. Just even the sight of me grabbing them made Jen moan knowing what was to come. I pulled her lacey bra down just enough to expose both pink nipples. Jen was so turned on that her nipples were already hard. I wrapped my hand around her left breast, pressing her nipple out as far as I could and applied the clamp. Jen moaned my name as her legs began to tremble. I licked the very tip of her clamped nipple and flicked it with my tongue. She began to shiver. Moving to the right, I did the same. Only this time, as I applied the clamp to her right nipple, Jen's body contracted and she gushed out with a squirting orgasm.

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"Fuck, already? My skills are getting sharper!" I half asked, half laughed in amazement.

"Oh my god, that felt so fucking good!" Jen gasped, "I haven't cum since we fucked on Tuesday. I was waiting for today."

"Well then, we have a lot to make up for," I replied, my amazement slipping away and my sexual focus returning.

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I gave Jen a few more kisses, before turning her around to face the edge of the bed. The carpet was already wet beneath our feet and her black heels gleamed with droplets of squirt. As I stood behind Jen, I wrapped my arms around her, working my way up her body, until one of my hands found her soft pale neck. I gripped softly at first, leaning her back to kiss her. As she turned her head to meet mine, I applied more pressure, choking her as we made out. She moaned but was muffled as my hand pressed harder against her. Just when she began to really sink into it, I released her and pushed her over, face first onto the bed. Her bare ass was right at my waist level. She begged me to fuck her. But I had other plans.

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Reaching over Jen, I grabbed a few of the toys she had lined up on the bed. As I did, my waistline grazed her ass. Jen could feel how hard and thick my cock had become through the silk pants and boxers she had bought me. She again begged me to fuck her. I ignored her. In fact, I told her to be silent. The more she begged, the longer I would take before fucking her. I told her that every time she made a noise, I would spank her. She nodded in acknowledgement. As she stood there, bent over the bed, nipple clamps on, already soaked in squirt, I took my time to decide which toy I would start with. I selected the magic wand. Throwing a towel down just behind Jen, I unbuttoned my silk shirt and placed it on a nearby chair. I knelt down on the towel just behind her. I unzipped her thong just enough to expose the entirety of her pussy without taking it off. Her pink lips were swollen and glistening. Everything about her body said she was aching for me. I traced the outside of her lips with my finger, and then slipped it inside of her.

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"That's not so bad, is it?" I asked.

"No Daddy," Jen replied, "It's perfe---!!!"

Her voice shot up into a scream the moment I clicked on the magic wand in-between her legs. Jen's head had been down in the bed and towels so she had very little idea as to what I was up to. She tried to raise herself up a bit to stave off some of the intense vibrations, but her legs were going weak which brought her clit down even harder upon the wand. At the same time, my finger worked its magic on her G-spot and within less than 30 seconds, she screamed that she was going to cum. I knew the drill by this point and slipped my finger out of her, just as I felt her cervix come slamming down in a big internal contraction. At the same time, I lined myself up perfectly for her to squirt all over my mouth and face. She screamed my name as she came all over my face. Her squirt was warm and sweet as it had been the two times I tasted it prior. Today seemed to be even sweeter though. I let Jen ride the waves of her orgasm down, holding her to keep her from collapsing. Once she was calm again, I leaned over to her on the bed and made her kiss my squirt soaked face. She was obedient and even licked some beads of squirt that were dripping off of my chin.

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"Was that a good one?" I asked.

"Yes Daddy," she answered.

"Good, but unfortunately, you were too loud. I told you that you had to be quiet. So now you have to be punished," I replied.

"Please, no!!!" she begged.

I reached for the riding crop. Standing to the side of Jen, with her ass exposed and bent over the bed, I placed one hand on the small of her back. I raised my other hand... CRACK! The riding crop came swiftly down across her ass, instantly leaving a red stripe. Jen let out the shortest, sexiest scream, but I deemed it too loud. CRACK! Another stripe, another scream, even shorter this time. Jen had caught on. CRACK! This time, Jen was silent and took her punishment. A small stream of squirt leaked out of her with the last spank. Jen already looked exhausted, and we were just barely beginning.

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Setting the crop down, I resumed my kneeling position behind her. I selected a small purple bullet vibrator with a long tail, all while kissing the red stripes across her ass. Her pale creamy skin amplified the redness. I worked my lips and tongue across them, cooling and soothing her until finally, my tongue found her pussy. She let out a soft moan. I licked and sucked on her pussy lips and clit. She wiggled and shivered with pleasure. I slid my tongue in and out of her, distracting her as I got the vibrator in place on her clit. Just as I had done with the magic wand, I turned it on in place. The intensity was so shocking to Jen that she immediately squirt. It was only a small one and not enough to be a true orgasm. She shivered all the more as she felt me drink as much as I could straight from her pink lips. I worked her clit with the vibrator and ate her pussy with a hunger she hadn't experienced in years. She kept squirting small little squirts with practically every lick, every suck. She was cumming over and over. Jen later confided in me that she was so turned on by the thought of me, a young man dominating her and eating her, that she came multiple times just from that thought alone.

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Although Jen was cumming repeatedly, I wanted to really hit her with a big orgasm. For as experienced as she was, she had never had a partner who was interested in anal play. So in that heated sexual moment, I chose to try. I moved my tongue up her pussy to her taint and began to suck on the tiny, pale stretch of skin there. She moaned hard, and I knew I was headed in the right direction. As I teased towards her tight pink asshole, I moved the bullet from her clit and slid it inside of her. She tried to squirt it out, but I held it firmly in place. Jen moaned hard now. Her cuffed hands clenched at her sides. With one hand, I used my thumb to keep the bullet inside her, while also rubbing her clit with my fingers, and with the other, I attempted to spread her ass as wide as I could. Taking the hint, Jen used her cuffed hands to reach back and pull her ass cheeks apart. Her hands were red from clenching with ecstasy, and when I was finished with this round, her ass would be also.

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I moved my tongue from her taint and began to lick her pink asshole. I worked it all over her tiny little hole, Jen moaning incessantly with pleasure. I noted this, as I would punish her later, but for now, I was laser focused on a huge orgasm. I used my thumb to hold that bullet vibe right against her G spot, and I rubbed her throbbing clit faster with my fingers. Jen moaned that she was very close. My tongue licked circles around her tight pink asshole until I heard that she was close. At that point, I began to nibble very softly on that tight little hole of hers. That sent Jen over the edge. I was not prepared. Before I could react, Jen's asshole tightened and she contracted hard. The bullet vibrator came ripping out of her pussy, practically breaking my thumb from the force. The huge gush of squirt that followed, defied biological law. Jen covered me in squirt, and stood shaking violently. I quickly shot up to keep her steady and hold her tight against the bed. She shook harder than ever before. It was at least 2-3 minutes before she could even speak.

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"Fuck, Daddy, you ate my ass," Jen gasped for air between words, "Fuck I've never felt anything like that before. It.... it was.... amazing!"

"I am glad," I responded, still shook up a bit from just how hard Jen had orgasmed, "We should probably stop though, since that one was so intense?"

"No," Jen paused for a moment to catch her breath, "We haven't even gotten started, Daddy." The air of defiance in her voice immediately cut me, and not in a good way. I looked Jen dead in the eyes and her fire flashed bright for just a moment, but then was cooled by the soft blue of her irises. Her submissive puppy dog stare was back. Only this time, I was determined to break her.

"Fair enough. Put your head back down on the bed now." I replied in a authoritative tone, placing my hand on the small of her back.

CRACK!