Description: A young man becomes involved with a mature woman who was previously his boss. Quite unexpectantly, he has to decide if he is willing to play Jill’s kinky game.
Jill’s Game or An Unexpected Turn of Events
By Mugsgame
Our team was having a late lunch to celebrate the wrapping up of the project on a Friday afternoon at a nearby restaurant. Jill had been the project manager and my direct supervisor for the last year. As of Monday, she was starting a new position with a different company. The rest of the team and I would be moving on to different projects next week as well. Jill was a handsome, full-figured, and statuette woman 15 years older than me who I found striking from the moment I had first met her.
Jill usually wore skirts with a blouse usually along with a blazer. She had had long, dirty blond hair that fell around her face. Jill was a decisive leader with extensive knowledge which she willingly shared. She could be funny as well. I sometimes wondered why she had never married. I certainly had always found her to be a very attractive lady who was very desirable. Given the opportunity, I would have asked her out if she was not my boss despite the difference in our ages.
The restaurant had placed us in a separate dining room with a few tables placed in front of a back booth running the length of the wall and a partition that separated the large dining room into smaller ones. During lunch, I was sitting opposite Jill a table away and noticed the outline of her bra through the sheer blouse she was wearing. I must have been looking a little too intensely because Jill to smirked at me, before turning away to speak with someone.
I was embarrassed, wondering if others had noticed. My thoughts turned to other meetings that we sometimes had in her office. More than once I had noticed what bra she was wearing through her blouses. The bras were almost always lacy ones. I always tried not to look or take notice. It was a losing proposition; I always did notice.
Although I tried to be discrete about it, I was pretty sure that Jill sometimes caught me looking. She never said anything but would give me a knowing look. I always felt foolish, completely out of my depth when I caught those knowing looks. It almost felt like a child being caught with their hand in the cookie jar. Jill always just carried on. Other than that knowing look, she never made any mention of it.
After having lunch, you could either go home early for the weekend or stay and have a drink or two. People started drifting away saying goodbyes. I stayed with a few rounds of drinks being ordered as people chatted. As more people went home, we moved closer together. Finally, we were down to a little more than half a dozen after starting with a group of around twenty people.
Jill had gotten up to use the restroom and I did so as well a minute or two later. I ran into Jill as I was coming out of the men’s room in the little alcove where the restrooms were located. Jill was tall wearing heels that made her tower over me. I bowed slightly motioning for her to proceed ahead of me back to the tables. Jill smiled warmly, I followed her admiring her long nylon covered legs as we made our way back to the tables.
I found myself sitting on the end of the booth next to Jill with a few people sitting opposite us with a couple further down the booth. Before a last round was ordered, a few more people left. At the moment no one was sitting directly opposite us. Jill had turned away from me talking to the woman beside her. I was following the conversation. Without quite realizing how, I found my hand resting on Jill’s knee. I was a little bit drunk, but I don’t think I made any kind of conscious decision to put it there.
Jill glanced back, looking at me sharply. I didn’t quite know what to do or say. After a pause, I just looked up at her with a dumb smile on my face. I shrugged my shoulders, giving her knee a light squeeze. Jill just gave me a quick smirk turning to continue the conversation she was having. As she turned, her legs parted a little. I did not know what to make of that when she glanced back, winking at me. My cock started throbbing as I slowly edged my hand around to her inner thigh and started stroking higher.
As my hand went higher and higher, I started to press against her panties. Jill turned back to me discretely waving a finger signaling no no. My cock was throbbing. I wondered what had just happened. I knew that I had always been attracted to Jill. She had allowed me to touch her. Yet she slammed on the breaks. Was she just teasing me?
As the lunch broke up, I summoned up the courage to ask Jill out to dinner the following night. While I did not know a lot about her personal life, the gossip in the office was that she dated several men with no long-term ties. The ones I had heard about or seen around the office were lawyers or executives much older than me. I am not very sure how or why but Jill agreed to go to dinner with me.
When I picked Jill up, she was wearing a knee-length white crinkle peasant skirt with flats along with a flowered print blouse. She did not quite tower over me the way she usually did in heels. We went to a small Italian restaurant that she knew sitting on opposite sides of a booth. I ordered a bottle of Chianti.
With Jill no longer being my boss, the conversation flowed much more easily. I did not feel as awkward as I usually did with her. We talked a little more about our backgrounds and I said that I was of Swiss/German descent. Jill smiled saying that her grandmother was German and had emigrated to America between the wars. She also spoke a little German that she had learned from her grandmother. Before drinking the last of the wine, Jill got up to use the restroom and I again admired her long shapely legs as she walked. When she came back, Jill sat in the booth beside me.
I could feel the warmth of her body next to me and smell the perfume she was wearing. I froze not knowing what to think or say and Jill reached up and turned my head to face her. She was smiling. Jill winked at me before reaching for my hand and placing it on her knee. I could feel my face flush as I rested my hand on her bare flesh. I quickly looked around. We were sitting in the last booth and there wasn’t anyone at the tables opposite.
As I started running my hand higher up her inner thigh Jill whispered in my ear “you have such soft hands, but I have an early flight out to the west coast tomorrow.” I signaled for the bill before driving Jill home, parking in front of her apartment building.
Jill was about to get out of the car but I said “Stop.” Jill looked at me and I took her hand and kissed it saying: “I will be thinking of you and hope that we can go out again once you are back.”
Jill smiled leaning down kissing me on the forehead saying “I will be looking forward to that.”
Over the next month, we started going out most weekends and on the third date Jill packed a lunch and we drove to a state park and spent hours walking the trails and chatting on a warm spring day. When we got back to the car there were picnic benches with a view of a lake, and we ate and drank some cold pops.
Jill was wearing a blue blouse with cutoff jeans with her hair tied back in a ponytail. I thought she looked lovely in anything she wore. Jill then noticed me staring and silently placed my hand on her thigh.
I smiled at her and said, “I look at you and see beauty both in and out.”
She looked at me and asked, “Why do you think that?”
“You know that you are a beautiful woman. But I also I remember seeing you walking on the street a couple of blocks away from the office. Most people ignore the homeless, it’s almost as though they are invisible. There was an old man was sitting on some steps. As I watched, he said something as you passed. You stopped, taking a few minutes to listen to the old man before opening your purse, giving him a few bills. That is kindness in action. I can’t fathom what you see in me, but I am glad that you do see something.”
There were not many people about and at this point I didn’t care as I stroked Jill’s thigh. Jill leaned over and kissed me and whispered in my ear “You are smart, kind, and caring. You are also very handsome, even more so because you don’t even realize it” and she laughed as I felt my face flushing.
On the drive back to town and with the AC on I glanced and noticed that Jill’s nipples were showing through the blouse. It seemed that the more I tried not to look, the more I felt compelled to.
Jill was smiling as she glanced down at the growing bulge in my pants and said “I have a nice bottle of wine at home if you would care to join me?”
“Of course, I would” I replied hopefully not showing how my heart was beating like a hummingbird’s wings. I tried to calm myself taking some deep breaths and keeping my eyes on the road. When we got back to her apartment, Jill opened the bottle of wine pouring us each a glass. Jill was comfortably guiding the conversation until I got up the nerve to put my hand back on her knee.
Jill leaned over kissing me lightly on the lips, using her hand to press my head against her bosom. I could not believe how soft they seemed against my face. Together with the scent of the perfume she was wearing I felt myself getting more and more excited by the second.
I glanced up looking into her eyes as I pulled back, slowly unbuttoned her blouse. Jill was wearing a sheer white bra that clearly showed her hard nipples poking through. I bent down to lick her nipples through the bra, reaching around her to unhook it with my trembling fingers. I was hardly smooth in my attempt.
Jill smiled, reaching back to undo it saying “Let me.”
I took her boobs in my hands and fondled them before leaning forward to suck her nipples. I was sucking them softly for several minutes. Jill was softly moaning as I started biting on her nipples. She then guided my hand up her thighs. I started kissing her as I ran my hands up and down her thighs. I was in heaven, getting down on my knees in front of her. I unbuttoned her cutoffs, pulling them off as I kissed up Jill’s inner thighs. The scent from her pussy was almost overwhelming when my nose nudged against her panties.
I pressed my face against Jill’s panties. I was excited to feel they were not just damp but actually wet. I started licking her pussy through the panties, sucking on her pussy lips. Jill reached down pulling the crotch of her panties aside. She then pressed my face close against her pussy. When I got my tongue buried deep in her pussy, she closed her thighs tightly against my head.
I could hardly breathe but could hear Jill’s muffled voice repeating “Don’t stop, don’t stop, don’t stop” as I drove my tongue deep inside her until a hot wetness washed over my face. Jill’s legs relaxed. I was sputtering, catching my breath when I looked up to see Jill beaming at me.
Looking up from the floor, I could not believe I was seeing Jill’s lush nude body. It seemed she should be a renaissance painting with her heavy breasts falling down her chest, her rounded figure and pussy parted with the lips spread with her clit poking up. But what satisfied me the most was the smile on her face, knowing that I had been able to please her.
Jill reached down taking my hand, leading me to her bedroom. I would like to say we made passionate love all night long. Instead, I embarrassed myself and came almost right away after first entering her. I must have looked crestfallen.
Jill rolled over on top of me, kissing me before whispering in my ear “It will be better next time, now snooze and I will be back soon.”
I could hear water running in the bathroom. I must have dozed a little as I woke with Jill sucking my nipples. She would alternate sucking one, then biting down on it. Sometimes she bit quite hard. No one had ever done that to me before. I felt myself getting aroused again.
I lasted quite a while that time with Jill riding on top of me with her hair falling down across her face. I was extremely pleased that we both managed to cum together at the end.
As Jill got up to use the bathroom again, I said “I will wait for you to finish.” Jill just smiled, taking my hand before leading me to the bathroom.
Growing up with sisters, for the most part, I peed sitting down. As I sat on the toilet peeing, I saw Jill running water in the bathtub, filling a red rubber bag that had been hanging from the showerhead. Jill hung the bag back, squatting in the bathtub with a hose running from the bag between her legs.
As I came around to face her Jill just smiled without any embarrassment whatsoever saying “It is much better to clean oneself after sex.” I watched as she squirted out the douche water thinking in a weird way it did make sense. I had just never known or even heard of a woman doing that before. We made love once more that night, with me falling asleep to the sound of water running in the bathroom.
We continued seeing each other most weekends, sometimes even a couple of times a week when she was not traveling. One late summer evening, when Jill got back to town late, we went to a little neighborhood restaurant for a simple dinner. Afterward, we went back to her apartment.
After the first fuck, Jill had gone into the bathroom, I was still feeling very horny. Her wet panties were laying on the bed. I started stroking myself with her panties pressed against my face when suddenly I noticed Jill standing at the foot of her four-poster bed smiling down at me saying “So are you a kinky boy?”
I was embarrassed at being caught jerking off, especially with her wet panties. I watched wordlessly as Jill crawled onto the bed on her hands and knees. She straddled me, sitting on my stomach. I could feel her wetness against my belly as she took the panties from my hand and tossed them on the floor.
“I have better games to play” Jill said as she sensually ran her hands over my face, running her fingers through my hair. I was lost in the feelings of her hands moving over me. Jill had a sly smile on her face as she covered my mouth with one hand. After a long pause, she pinched my nose shut with the fingers of her other hand.
Jill looked down at me critically as I tried to process what she was doing. I didn’t know what to think. After a minute it was uncomfortable not being able to breathe. I struggled against the hold she had on me. Jill was strong with her hands keeping their grips tightly over my mouth and nose.
Soon, I was getting desperate. I was trying as hard as I could to break free. Jill kept looking down at me completely calm, smiling with her long hair flowing over her face while maintaining the iron grip over my mouth and nose. Finally, Jill moved her hands away with a flourish. As I took in great gulps of air, Jill had a triumphant look on her face. I think I had tears in my eyes, trying to comprehend what just happened.
Jill glanced over her shoulder, sliding a hand over my hard cock saying “Well your cock didn’t seem to mind, how do you like playing my game?” No one had ever done anything remotely like that to me before. I had also never even heard of anything like this, Thoughts were racing through my head. What did I feel? Just what the hell had just happened? Did I want to get up and get as away as I could?
Her words thundered through my head “My game” Jill had said. I am sure that I had never before felt so helpless or felt as much fear as I had just experienced. Some game I thought. That I was even thinking about it as a game surprised me. It suddenly dawned on me that I feared continuing her game. This was felling vulnerable to the ninth degree. Yet at the same time, on some deep level I desired it without quite understanding why.
It dawned on me that I felt completely safe in Jill’s hands. What I desired most was seeing again the look on Jill’s face as she both caressed and smothered me. Was it erotic? Certainly, yet it was almost as though she was in a trance above me. Jill looked beatific. Knowing that I was pleasing her immensely sent shivers down my spine. Jill waited patiently for an answer with a sly smile on her face. I found a calmness within myself overcoming my trepidation.
I nodded my head saying “Yes.”
Jill ran her hands over my face again before kissing me. She then got up off of the bed, going to a dresser. Jill opened a drawer, taking some things out. As she stood over me, she tossed a pair of black leather gloves onto my chest. Jill then took my right arm wrapping a leather cuff around my wrist.
The cuff was padded on the inside and before she buckled the cuff to my wrist she said: “Last chance, are you sure you want to play my game?”
I had seen such bondage stuff before but it had never appealed to me. Tonight, it was like a bolt of lightning striking down my back. Regardless of my doubts, I wanted nothing more as much as pleasing Jill. I found myself tongue-tied. Finally, I looked up at her smiling down at me and nodded.
Jill then buckled the cuff snug but not tight. She used a cord and looped it around a ring on the cuff and tied the ends to the post of the bed, I felt a rising panic setting in as I wondered what on earth I had gotten myself into. At time same time I felt my cock throbbing and twitching.
As she walked around the bed to cuff and tie my other wrist, Jill nodded toward my twitching cock remarking with a laugh “It looks like you like my game so far but it’s far from over yet.”
Jill climbed on the bed again and I again felt Jill’s wetness on my stomach. Jill draped the gloves over my nose and face and said “Hmmm we will see if you like the way these smell as much as my panties.” The leather gloves felt soft against my skin with a deep rich scent of leather. I felt my cock twitching even more as I watched Jill put on the gloves that reached halfway up her forearms.
After flexing her fingers in the gloves, Jill again straddled me, beginning to run her hands over my face and through my hair. It was a weird feeling. I was almost losing myself under the intense look Jill was giving me together with the sensuousness of her touch. Suddenly, without warning, one gloved hand clamped down even tighter than before over my mouth. Jill took her time before pinching my nose shut all the while looking down at me smiling broadly.
I remember looking up wanting to please her. After more than two minutes passed, I tried to stop my rising panic. Without realizing it, I became aware that I was straining as hard as I could against the cuffs and her grip on my mouth and nose. Jill watched calmly as I struggled more and more. I felt her maintaining her strong grips as I writhed under her.
How long it lasted I could not really tell you. I remember trying to think about not struggling but at the same time felt my entire body was shaking uncontrollably as Jill gazed down at me, her leather gloved hands tightly gripping my mouth and nose. Without warning Jill released her holds again with a flourish.
I gasped, drawing in air, choking at the same time. I felt spittle running from my mouth and nose. Jill calmly climbed off of me, picking up the panties she had earlier thrown to the floor. She bent over me using the panties to wipe my face, then climbing back to sit on my stomach.
Jill bent forward, kissing me with her tongue probing my mouth as she whispered in my ear. For the life of me, I don’t remember what she said. My heart was racing. My head was pounding. I felt both great fear as well as an utter calm coming over me as Jill continued whispering in my ear with her long hair tickling my throat.
My twitching cock, the weight of Jill sitting on me, the cuffs that were restraining me all me struck me with force. This wasn’t a dream or nightmare. The totality of everything happening made me realize that this was really was happening to me. This was Jill’s Game and I could not comprehend it.
Jill started stroking my face asking “Do you want to keep playing my game?”
I wondered what I really felt. On one hand, I was more than a little frightened. I realized that I was literally placing my life in Jill’s hands. I was placing more trust in Jill than anyone else I had ever known. Yet at the same time I felt a deep contentment which puzzled me.
Then I felt a chill of excitement sweep through me as I realized that I was determined to proceed. Seeing the beatific look on Jills face was worth enduring anything I thought. I nodded my head, trying to smile back at Jill.
I was not surprised when Jill stopped stroking my face, again clamping her hands over my mouth and nose. As the game went on it might have been my imagination, but I seem to remember each session lasting longer than the last.
I felt myself growing weaker and weaker, more ready to surrender to the dark. At a certain point, when my body was thrashing, it as though it was not happening to me. Or at least to some other me. I remember the sight of Jill’s face looking down at me looking extremely pleased. After releasing her hold each time, Jill drew me back with her touches and whispers always asking if I wanted to continue.
The last time that I remember, I sunk in deeper than before. I do not remember struggling at all. Just looking up at Jill, not wanting to disappoint her. I remember passing into a different state, suddenly it was as though I was outside of my body observing everything.
Seeing the joy on Jill’s face as my body was squirming and thrashing on the bed with her maintaining her grip over my mouth and nose as my body struggled against her.
That was the last thing I remember before I slowly shook off the cobwebs and became aware of Jill humming something soothing in my ear. Did I pass out? – I had no idea. I must have moved because Jill leaned over so that her face was just above mine.
Jill had a serious look on her face, sweat was beading on her forehead and her hair looked damp. Her hair was partially draped over my face. She started using a finger to trace patterns on my face. Jill then shifted her body and I heard a plop, suddenly realizing that at some point she must have gotten my cock inside her.
It was not hard anymore and I wondered if I had cum. Jill smiled broadly as though she could read my thoughts. She moved a hand down between her legs, bringing two fingers up to my mouth.
Without thinking, I opened my mouth, eagerly licked her fingers as she said: “You can have a little taste of us tonight but next time you are going to help clean me up.” It slowly dawned on me what that implied. After everything that had happened, I started laughing. Jill laughed too, looking extremely pleased with herself and me.
Jill then had a determined look on her face, gazing down at me for a long minute. Her expression was serious as she said “You did very well. Most flee before the game even really starts. None have pleased me more or lasted as long as you. Would you want to play my game again someday?”
I stopped and thought about it with Jill looking down on me. As I felt the weight of her above me, I knew that this was not a dream. Yet it still somehow seemed unreal. I had never dreamed of anything like this before. Thinking logically, it was dangerous. It was frightening. Somehow it was also oddly exciting.
But more than anything else it was the pleasure I gave Jill that pleased me the most. Just contemplating all of this I felt my cock twitching and getting hard again which surprised me. The realization dawned that I did want to play Jill’s game again. I positively wanted to play.
With determination, I said, “Yes, very much yes.”
Jill continued saying “Then there is something you need to remember now” as she bent down kissing me deeply. She suddenly bit down hard on my lower lip. I could taste blood in my mouth. Jill looked down at me with a look of satisfaction on her face.
She lowered her head and started kissing down my neck. When she reached my shoulder, Jill bit into it hard. I felt my body freeze as I endured the pain without crying out. When Jill raised her head there was a little bit of blood on her lips, as she said “You belong to me now. I have marked you twice.”
With that Jill got up, took off the cuffs and covered me with a sheet and blanket. She nodded towards my now hard cock remarking “We will take care of that in the morning, no more playing tonight, you need some rest. Now close your eyes and sleep, Liebling.”
I closed my eyes listening to Jill leaving the room. After all that had happened, I did not think I would ever get to sleep with my thoughts racing like a run-away train but the last thing I remember is the sound of running water coming from the bathroom.
The end
If you made it this far reader, I hope that you enjoyed the tale. Feedback and comments are welcome whether you liked or disliked the tale.
With many thanks to my editors Ravenna933 and ChancesAre whose wise comments and suggestions helped me improve the story.
Any errors or omissions are the authors alone.