Flattered Or Insulted

I took a chance as I was dancing with my best friends mum at an early spring BBQ we were having at my parents' house, I was surreptitiously admiring her full mature body, looking back it must have been the drink I had consumed otherwise I would never have said what I did.

Everyone, both adults and teens were mixing well, all dancing together irrespective of age although all the kids are over eighteen, it was such a fun cool vibe, music was blaring out from the stereo system dad and I had rigged up, and happily drinks were flowing and for once mum wasn't nagging me about watching my intake of booze, she was too busy consuming copious amounts herself. Getting louder and louder as the night wore on and becoming more and more flirtatious.

I had wandered over to Jane, Andy's mum and asked her to dance as she was standing all alone, looking wistful, after a brief hesitation she said yes, following me to where everyone was dancing, but only staying on the edge not getting into the middle of the crowd.

"You know Mrs Atkinson if you were a cougar I'd be willing prey." Oh my God, had I just said that!

She stopped dancing and looked at me shocked, "What did you just say? What did you call me?"

"I'm sorry, that came out wrong, I'm not saying you are a cougar or a MILF, but if you were I'd be happy to be your prey." Oh God, I was in big trouble, I'd blurted out what I was thinking. But my best friends mum is totally hot.

"So, young mister Smith, you think I'm a cougar or even worse a MILF." She looked angry, no hint of a smile on her face, just that stern look only a mother can conjure up to put a teenager in their place. I was in big trouble, and I knew it.

Not letting me get a word in to explain she continued, "And why is that, what gives you the nerve to think that, to say that to me?" But the strange thing was although her looks were angry and her words stern there seemed to be a twinkle in her eyes.

"Why do you think I'm a cougar, preying on younger men, or boys?" the boys said with such heavy contempt and obviously aimed at me.

"Well, Mrs Atkinson..."

"Oh call me Jane, you can't keep calling me Mrs Atkinson if you think I'm a MILF."

"Well Jane, you are gorgeous, dead sexy, that's all."

"That's all, you think your best friends mother is gorgeous and sexy?"

"No, not sexy, dead sexy," I replied, getting bolder and intrigued by the way the conversation was going, I had to hold my ground and not back down. I had a feeling that if I did she would tell my mum what I had said, and that was a definite no-no.

"Sorry, dead sexy, that makes it even worse. I'm not sure if I should feel flattered or insulted. Insulted that you think I'm old enough to be a MILF, or even worse a cougar, or flattered that a young man like you should find me "dead sexy.""

"Jane, I'm sorry I was wrong to say what I did, and I'm not implying that your old, that's not what I meant, and you know it, but if I were you I'd go for the flattery, as you are dead sexy."

"No, you shouldn't have said anything, but you were obviously thinking it. You are a very naughty boy, what would Andy say if he knew what you had just said to me, about me?"

"Oh, the same as I did when he said it about my mum. Cool."

Now that shocked her, more than what we had been saying, the fact that two eighteen-year-old teenagers could discuss that they found each other's mums sexy and be "cool" about it.

We had resumed dancing while this conversation was going on but had drifted to the edge of the dance area and had eased behind some bushes that prevented us from being seen.

"Colin, you are a very presumptuous and naughty boy, saying things like you have to me."

With that she placed a hand on the back of my neck, drew me in close to her and kissed me, pushing her tongue into my mouth, which was slightly open in shock at her actions. My surprise grew even higher when her other hand grasped my hand and pushed it up under her cropped halter top, and onto her medium sized right boob, forcing me to squeeze on it. As my fingers brushed her nipple it hardened instantly. As I continued to kiss and fondle her boob I got a sense of the full weight of it. Heavy and firm. A mature woman's breasts, not teenagers that I was becoming used to.

Jane moved her hand from mine, and with a quick movement, dropped it to my pants, opened the zip, pushed her hot hand inside my briefs and pulled my erect and throbbing cock out. Taking hold softly in her fingers she stroked it three or four times. God, it was heaven. Heaven until she stopped and backed away smiling.

"Colin, you are a very cheeky boy, and cheeky boys need to be punished. So, your punishment is not getting a finish and having to wonder at how good that finish could be. To be frustrated and longing." She smiled devilishly at me at that, "But, you have probably got a memory to help you get off on for a while. Don't get a sore wrist!"

With that she walked away, smiling and swinging her arse and hips, taunting me. I had taken a chance and pushed things a bit, and I had met my match, she was right I had been cheeky and I was more than frustrated now.

Over the next month, I had bumped into Jane on numerous occasions, and everything seemed to be the same between us, she didn't treat me in any way differently from before, apart from the fact she would occasionally give a little growl when she knew nobody else could hear.

Early one Sunday evening I got a text from Jane, we all have each other's phone numbers for safety and things like that. "R.U. free, come to mine @ 8.00 use back door, don't be seen. Cougar"

I replied, "What?"

"R.U. man or boy, got the balls, or were you all talk?"

I knew she was alone as Andy and his dad had left on a rugby tour that morning, I should have gone as well but was injured so couldn't go, even for the drinking and partying that was sure to happen.

At eight I was knocking on the back door of Janes house which is just across the street from mine, having made sure nobody had seen me.

Jane opened the door and what a sight met my eyes. Jane in a black silk, floor length nightdress, slit to the hip up one side, her firm and toned thigh pushed provocatively through it, with a plunging neckline that showed off her cleavage to best effect, a pair of kitten-heeled mules in red and a matching black silk robe completed her outfit. Although I couldn't see it I sensed that she was naked underneath the nightdress.

My mouth dropped open at the sight of her, she looked stunning even for a forty-seven-year-old mother of two, Jane is a couple of years older than my mum, and they have been friends for years.

I had seen lots of Jane over the years to know her figure is full and toned as both families have been on numerous holidays together in the past, plus BBQs and things like that where she is in a swimsuit or shorts and crop top, but this was something else to behold.

"Well you have got some, come in, and stop drooling," she said as she took hold of my wrist and dragged me into her kitchen, not stopping she led me up the stairs and directly into her bedroom, closing the door behind us.

Looking at me with a glint in her eye, I realised she was a cougar and I was about to become her prey.

She came close to me, brushing her body against mine and then whispered in my ear, her hot breath tickling it as she said, "Take your clothes off, everything, strip. Naked. Now!"

As she said this she stepped away from me and sat down on the edge of her bed, eyes fixing me with her stare. A smile of amusement crossing her face as I struggled to get out of my clothes I was so eager.

When I was totally nude, cock sticking out hard and proud, Jane stood up again pressed her body against mine, the feel of it under her silk nightdress so erotic, then she grasped my balls in her hand and squeezed gently. I was totally in her control.

"Colin, you are a very naughty boy, and with an even dirtier mind I suspect, now you need to be punished," with each word she squeezed my balls, making me squirm, every squeeze being harder than the last. But the hot warmth of her hand as it held me was so soft and sensuous even as it squeezed harder and harder I was almost cumming there and then.

"Now, you have to earn my respect and trust back. Have you had oral sex, I mean performed oral sex on a woman?"

"Err, yes a couple of times Ang..." I stopped speaking, I had made a terrible mistake, I was going to say Angie, and Angie she knew was her daughter who I had just started going out with."

Eyes, wide she squeezed my balls harder, this time hurting more than playful, "Have you had oral sex with my daughter, and don't lie?" With an even stronger squeeze, this wasn't fun she was beginning to hurt me now.

All I could do was nod my head.

"Have you had sex with her, full sex?"

I knew I had to tell the truth, "Twice, and she was my first." Her grip on my balls tightened, even more, I was squirming in agony.

"So daughter first then mother afterwards, what do you want to be able to compare us? You really do need to be punished, making a pass at not only your friends' mother but also your girlfriends' mother. Boys!"

Again she sat on the bed, "Kneel, on your knees in front of me." A command. Fortunately she had let go of my balls by now.

I sank to my knees and realised I was between her legs, Jane then pulled her nightdress up until it was above her hips giving me a full view of her shaven pussy.

Grasping hold of the back of my neck she pulled my face forward as she lay back and ordered, "Lick me."

She pulled her outer lips open just as my mouth made contact with her and instinct took over, my tongue pressed forward and I got the first taste of her, honey sweet yet tangy at the same time, and a sensuous musky smell coming off her in waves. She wasn't wet yet, but still well lubricated.

I licked up and down her slit, time after time, tongue probing and teasing as I became more bold and confident, lapping at her. Using my tongue deep in her at times, then others concentrating on just her outer lips, her juices were coming greater now and I could feel them covering my face in a sticky mucus.

Jane was not moaning but was uttering words of encouragement and guidance, but she would never let me touch her with my hands, every time I tried to push a finger into her or rub her pussy, she slapped them away, always instructing, "Mouth and tongue only."

Jane arched her hips off the bed and spread her lips wide open, exposing her clit more easily for me, not wanting to waste the chance and wanting to please her I sucked it into my mouth, holding it in my lips as I flicked it with my tongue.

"Shit, that's good," she half screamed as she held my head tight against her as she began writhing and bucking against my face crushed into her groin, her legs came up and clamped hard against me, prisoning my head.

Her breath was shortening, coming in pants now as her hips constantly pushed against my face, then with a scream she came, juices flooding out of her, body thrashing and bucking. She kept coming for what seemed like ages until at last her death grip on me eased and she lay back, a look of contentment and a dreamy smile on her face as I glanced up at her.

As I made to get up she said, "Where are you going, you're not finished yet. You still have to finish your punishment." If this was punishment then I wanted to be bad every day.

Jane had me lick and eat her out at least three or four times more that evening, cumming every time, her last climaxes running from one to the other. But she never allowed me to do anything but perform oral sex on her, no hands, not feeling her boobs, nothing. Then she dismissed me, just like that.

I walked home with a raging "hard on," frustrated, she hadn't touched me in a sensual way once.

Every night for the next five nights I would get a text telling me to go over, and every night I would be greeted by Jane in a sexy nightdress, and every night it would be the same, I would perform oral sex on her and pleasure her, and then go home with a stiff cock, full and aching balls and frustrated as hell.

One night when I arrived she had changed from her normal full-length nightdress and was in a babydoll style one, one that was so short it barely came to her hips, I'm sure I had seen the same one on Angie. That night she didn't take me to her bedroom but sat opposite me for an hour talking, legs on show, pussy bare and tantalisingly on view for me as she crossed and uncrossed her legs. Jane knew what effect she was having on me, the frustration, the torment she was causing in my mind. All the time teasing and taunting me. Then, as usual, I was instructed to get on my knees in front of her and perform my oral duties to her satisfaction.

One night I considered not going over, but I did. Why? Well, I suppose I was always hoping that tonight would be the night she would let me do more than lick her pussy, that tonight may actually be the night I would have sex with her. Fuck her. My best friends mother, my new on/off casual girlfriends mother.

Every night as I went home frustrated, the more my desire and wanting of her grew. I was entranced and captivated, in some ways, I was becoming her plaything, her toyboy, her slave.

Saturday night, Andy and his dad are due back tomorrow so this would be the last night I would receive her summons, and right on time it came, at five in the afternoon, but this time telling me to arrive earlier.

I sneaked over to Janes at seven as commanded, and when she opened the back door to my surprise she was dressed in a full length, fluffy housecoat, nothing sexy or teasing here. What was going on? What did she have in store for me tonight?

As usual, she instructed me to follow her to her bedroom and told me to strip, then she told me to have a shower, and make sure I washed my cock. Was this it? My hopes soared.

When I got back into the bedroom Jane sat me on the edge of the bed and stood in front of me, this was the direct opposite of our normal positions. When I was where she wanted she undid the tie of her gown and dropped it to the floor. She was stood there in a matching bra and panties set in bright red, the bra was a push-up style forcing her boobs high and together, whilst the panties were so sheer they were see-through, a black garter belt held up sheer dark stockings and her outfit was completed by six-inch killer heeled glossy red shoes.

My mouth dropped open in wonder and appreciation. She smiled at my reaction, my already semi-stiff cock springing to attention at once. Jane stood in front of me about a foot away from my grasp, I reached out my hands to her hips intending to pull her to me, but she playfully slapped them away, "Later," she whispered and at that moment I knew she wasn't playing, I would get to hold her body.

"You are a very, very evil boy, you needed and possibly still need to be taught a lesson, and I've still not made my mind up about you. But. I think I've teased you for too long now, and to be fair you've not complained. Why?"

"I just...I just...I just supposed I hoped that every night you would let me do more."

She didn't speak, just moved closer turned so her back was to me and then said, "Undo my bra."

My hands were shaking that much as I reached forward I wasn't sure I could do it, but after a couple of fumbles her bra was unclipped, Jane moved away, turned to face me and let the bra slide off her body, her full firm tits, with small rosebud nipples already hard, coming into my view. They were full and heavy a woman's breasts, with just the barest hint of sag, that made them so much more delightful.

A quick step forward and they brushed against my face for a brief second, then away again. Jane stood swaying in front of me for a few seconds, letting me run my eyes over her body, with its wide hips, long legs and her strong face, framed with scarlet hair, cut short.

Then smiling once more her fingers dipped into her panties and I watched as she pushed one into her pussy, moaning as she moved it in and out, then her hands were at the waistband of her panties, and in an instant they were around her ankles and apart from the stockings and heels she was naked before me.

Jane pushed me onto my back on the bed, positioned herself over me still standing, then taking hold of my cock placed it at the entrance of her pussy and in one quick movement slammed herself down on me, impaling my cock deep in her, I shouted out in pleasure as I felt it cup me. Jane stayed still for a fraction, both of us enjoying the feel of our cock and pussy together at last, then she surprised me yet again. Instead of pumping up and down she just rotated her hips round and round on mine, her pussy clenching and releasing on my cock.

Jane bent lower over me as we continued, letting me lick and suck on her boobs and nipples, at last, all the time she was constantly setting the pace of our fucking. I was getting near, and she could sense it, so she stopped and pulled off me. "You're not ready yet."

She lay down next to me on the bed and got me to play with her pussy, getting three then all four of my fingers deep inside her sopping velvety slit. How this was supposed to stop me cumming I don't know, as all it did was excite me even more.

Somehow my cock had softened but Jane didn't let it stay like that for long as she took me in hand and a few quick strokes later I was rock hard again. Jane climbed on top of me again, this time facing away from me, and as soon as I was settled in her, she started bouncing up and down on my cock, riding me hard, pulling up so my cock was almost out of her, then slamming back down on me as hard as she could, here arse making slapping noises as it hit my belly. The friction along my shaft as she rode down on me was unbelievable.

After about a minute of this I could take no more and without warning her I shot my cum deep into her pussy, hot spurt after hot spurt of cum, time and time again I fired my load into her.

Jane screamed in shock as the first cum hit her pussy and filled her, she slumped forward as my cock continued to fill her. Moaning and groaning, as she shook her head from side to side. Pussy clenching and holding me, then milking my cum from my already softening cock.

Jane stood and turned to face me a look of shock on her face, I could see cum dripping from her pussy as she moved towards me, then she dropped to her knees, took my soft cock in her mouth and cleaned every drop of cum from my body.

We rested for a while lying arms around each other holding and caressing until I felt my cock starting to stiffen again. Now I was taking the initiative, got Jane on her back took hold of her ankles and pushed her legs high and back so her knees were level with her boobs, her hips raised slightly and pussy easily available to me.

Not waiting I slammed into her hard, and kept slamming into her time and time again, as hard and as fast as I could, this in some ways was payback time for my frustration. I wanted to fuck her as hard and as violently as I could, and I was doing that. My hips were hammering at her like a jackhammer, pounding my cock deep into her, Jane was thrusting back at me just as hard and just as fast. Pussy slick and wet. I sensed her pussy trying to hold me, hips rotating, but the position she was in with me holding her ankles high meant I had all control now. And I was using it and her for my pleasure.

I hammered into her for about ten minutes, then let go of her legs, as I did she wrapped them around my waist pulling me into her and holding me in. Her hands flew to my face and she kissed me with a wild passion, tongue deep in my mouth, nipping and biting my lips, "I'm cumming," she groaned in my ear, hot breath tickling.

"Good," I replied. Jane tilted her head back, let out a primaeval scream of pure lust, thrust her hips up clenched and locked her pussy tight on my cock and came, eyes wide but out of focus. She kept cumming time and time again, little shudders and aftershocks running through her body, and all the time I was still humping into her.