A New Perspective

This story has a bent towards what I tend to think of as gentle femdom type themes, in this case involving an older woman and younger man. If that's not for you I completely understand.

All characters are clearly over 18.

Constructive feedback is always appreciated.

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Have you ever had that epiphany, the one that completely changed the way you looked at life? I did recently, and all I can say is that I've been taking a good hard look at all of my other preconceived notions, wondering how many of them have been wrong and how many people I may have put off or hurt because of them. You see, you'd think a wild night in bed is the type of event that makes a guy see stars, fall in love, or things of that sort, but for me it's all been a bit more philosophical.

I guess I'm babbling a bit and probably not making very much sense, so let me back up to last weekend when this whole story started. I'm 28, a little over six feet tall and about 170 pounds, with an athletic frame built playing baseball in high school and college and maintained with regular work outs in an MMA gym. If I'm being honest, I don't do MMA with the intention of ever competing, I just find it to be an intense full body workout that fits into my work schedule. Also, the bit of a douche in me likes knowing that if a guy got too pushy while I was trying to pick up a girl (who may or may not be his girl) that I could put him down.

Looking back now, I can also see that my approach to women and my dating life really make me wonder what screw was loose in my brain. You see, I definitely wasn't the guy you wanted dating your sister or daughter, since I'd lie, cheat and do whatever it took to get them in bed and then generally treat them badly once I'd succeeded without regard for the damage I left behind. But if I saw a female in danger? You better believe I'd want to be the one to swoop in and save them. I get it, super misogynistic of me and all, where I saw women as pathetic enough to need me constantly looking out for them and worthless enough to not deserve respect or empathy. I'm not excusing it, that's just the way I was. And man oh man, as the world turns...

You see, on the night in question, I was out at one of my usual clubs trolling for some fun but the club was dry as fuck that night, probably due to the horrible winter cold snap that had come through and the icy sub-zero temperatures. I finally gave up and as I walked out of the club and turned the corner saw the unmistakable silhouette of a drunk woman stumbling and sliding along in heels. I was kinda jealous, I'd barely got a buzz on, she seemed like she got her money's worth. From her silhouette I could admire the way her full round ass and thick luscious thighs filled her jeans, even as her waist tapered in sharply emphasizing her curves. I hurried to catch up, hoping to "save" her and maybe make the night worthwhile after all, but when I caught up I realized she was quite a bit older than me and the way she had a tight belt cinched around her waist made me think those legs and ass were nothing but jiggly cottage cheese and there was a gut just begging to be released.

At this point the tingle of excitement in my pants faded but I felt bad for her with the way she teetered around like bambi on ice, and the chivalrous part of me wanted to make sure she safely got into the cab she so clearly needed.

"Hey, you ok?" I called out to her, but she barely looked over her shoulder as she gestured for me to go away. If I'd just done as I was told everything would be different, but it wasn't the best part of town at that time of night, and I wanted to see her in a taxi before I bailed.

"Hey, slow down Babe. You're gonna fall!"

She stopped in her tracks and turned to face me. "Who the fuck are you calling Babe?"

It made me smile. In the shadows she couldn't see she was talking to a good looking young stud like me.

"You," I said, "You need to get in a cab before you break an ankle, Babe."

The last bit may have been said with a bit of a smirk and she muttered under her breath in annoyance as I caught up to her and slid in beside her and offered my arm for support. Begrudgingly she took it and we made our way onto the side of a main road with more light available.

"Come on, let's put you in a taxi so I can get home," I smirked.

There was something so much more hapless about drunk women compared to men. Their stupor seemed so much more brainless than mine. Instead of doing as she was told she sat down on one of the benches bolted to the floor. I sighed and sat on the opposite end.

"Don't fuck with me, alright? I'll hurt you," she said with a slur in her voice.

I could barely contain my laughter that this woman thought she could hurt me. I looked her up and down as she slouched on the bench. With more light I could see I was right about how she looked. Her jeans looked like they were meant to be a loose fit but they were about to burst from the stress of keeping her thighs inside. God, she must've felt like shit amongst all the other girls in the club with flat stomachs and thigh gaps and there she was, crushing her stomach with her belt just to get in the door. Don't get me wrong, curvy can be hot, but the way she was dressed made her look more chunky than curvy.

"How old are you?" I asked bluntly.

"An obnoxious opener, but 44," she replied equally bluntly. "And as for the question you should have asked, my name's Lisa."

"Bobby. What are you doing here?"

"My fucking..." She took a breath to compose herself and I prayed she wouldn't cry like they usually do. "I was supposed to go out with friends, but my ex flaked on picking my son up from band, so I had to go get him. And then the kid didn't even have the decency to thank me, just wanted to be dropped off at his father's house so they could chill. It felt like he blamed me for me ex not showing up. I spent two hours being an ignored chauffeur and figured I may as well go out just to make me feel like I hadn't completely wasted my night."

I wasn't really listening, just analyzing her looks in light of the new information. Honestly, fair play to her, I would've guessed 40 at the most. She had a little loose skin on her neck and wrinkles at the corners of her eyes and she had a definite hint of love handles pooling around the top of her belt but her upper body wasn't overly thick and her breasts, although probably aided by a pushup bra, looked nice and full. It struck me that she was probably really hot when she was younger.

"That sucks, that stuff with your ex and kid," I said as a taxi pulled over for her, "do you need any money?"

She slowly got up. "I don't need to take money off a child."

"Hey, I'm not a child, I'm almost 30."

She gave a wry laugh as she opened the door to the cab. She grabbed my wrist and said, "In that case, come have a nightcap."

I told you she wouldn't resist once she got a better look at me (although I still wasn't sure how many I'd need to get the beer goggles dialed incense I still wasn't feeling it). I pulled my wrist away, but nodded my acceptance.

In her state, she elected to get into the cab head first and crawl on all fours to the seat on the other side, so for a moment her big, denim-stretching ass cheeks filled my view of the door to the taxi and made me rethink just how firm and smooth those globes might actually be. I slid in behind her figuring what the heck, I could always slip out once she passed out if I didn't become interested.

As we pulled up to the house I was a bit nervous. I'd never gone into a woman's house at night without the intention to have sex with her. Scratch that, I'd never gone into a woman's house at night at all. Girls? Sure, plenty, but as I watched Lisa's ass test the strength of denim to new limits as she walked up the steps to her door, I couldn't refer to her as a mere "girl".

She grabbed a bottle of wine and a corkscrew and gave them to me with instructions to open it while she grabbed a couple of glasses. Once the wine was poured we settled on her sofa where I began to get the uncomfortable feeling that I was now the one being judged, the one being sized up. As she sipped her wine, her dark brown eyes scanned me slowly from head to toe, pausing at my crotch, which just made me annoyed at her feeling like she had the right to be judging me instead of just being grateful that I deigned to share my fit, hot body with her.

Her wandering eyes and silent confidence made me feel like the drunk one, and she suddenly seemed oh so sober. I hadn't touched my wine yet but it seemed to have settled her down, as she sipped away half the glass, never without a slow lick of the lips afterwards. I took a cautious sip of the wine since I was more of a beer guy and cringed at the heavy tannins as the wine washed across my tongue.

She sensed my predicament and gave the sort of warm smile that makes one's eyes narrow and crow's feet appear. In the light of her living room I got my first real look at her face. She was a little more tanned than I'd realized and her wavy brown hair beautifully framed her heart shaped face.

She got up and my heart skipped a beat as she was walked towards me but she picked up the remote from the shelf right next to me and selected a song. From my seated position I gazed straight ahead at the profile of her figure that was now just inches in front of my face. The depth of her thighs from quad to hamstring, the curve of her ass as it sloped out from her lower back, the width of her hips bending my depth perception. My hands quivered and my mouth went dry. "It's just fat, it's age, it's spare weight, it's not hot, it's I don't know" was all that ran through my head.

She started a slow instrumental song on a sound system that played throughout the house and turned 90 degrees. My vision was now filled with the zip fly on her jeans. Her round, thick hips inches from my face suddenly made me feel something alien: vulnerability.

"What are you waiting for?" she said, in a voice somehow much more controlled and smooth than she had seemed on the street.

Controlling the quiver in my hands I smirked and rolled my eyes to look away from her.

"Don't take up poker," she said, "I can see your erection about to tear through your little jeans."

With that she stepped forward and climbed on my lap, slipped her arms around my neck and laid a mind altering kiss on me, her soft, full lips molding to mine as her tongue gently but insistently slid forward to find mine. Her hands slid into my hair, her nails gently massaging my scalp sending tingles up and down my spine. I was completely paralyzed, my arms just hanging limply at my sides as my erection became so hard it was painful.

I can't remember the last time I was that turned on, that desperate, that out of control. To have such familiar, pleasurable sensations in such an unfamiliar way is an unnerving feeling. I seduced girls, not the other way around. I prided myself on making a girl wet, the other way around felt wrong.

As she pulled back, I shook my head and took a breath. So what? I'm drunk and my standards are obviously lowered. I was going to get free booze and sex. What was I overthinking it for? Give her the dick she clearly wants, fuck her, hope she's not into cuddling, leave her a fake number and get out of there. What's not to love?

As these thoughts were running through my mind she gazed into my eyes, seeming to see it all. Those luscious thighs tightened around my slim ones as she pressed her crotch into mine. She leaned forward and pressed her breasts into me as she maintained eye contact. Damn, those tits were firmer than they looked and I was becoming more aroused, confused and insecure by the second.

She just smirked into my eyes as she held me there, her fingers continuing to lightly stroke my scalp and play with my hair. Just when I thought I was going to burst from this surprisingly sensual full body contact she stood and took me by the hand.

As I followed her up the stairs I was once again staring at the wide, round pair of butt cheeks begging to be released. Her hamstring cut a deep crease that looked like a smile into the bottom of her ass on the back step of her stride up the stairs. I kept the hand she had a hold of steady but my other one shook. I looked away and saw a couple of medals and an old framed photo of a young softball player. So this was what I was looking at, the hard athletic body of a softball player filled out and softened with age.

As she took her clothes off, I got a flutter of nerves that made losing my virginity look relaxing. Her top came off and the pushup bra I had presumed was there simply didn't exist. Instead, her lacy black bra held what looked like a pair of large C cups topped with hard pink erasers that barely sagged when she slid it off. The belt came off and the gut I waited to drop out wasn't there, just a flat tummy with barely a touch of jiggle. Her faithful jeans revealed the enormity of the task they had been carrying out so reliably as she peeled them off, the hips they were holding in spilling over the brim of the jeans as they were dragged down. The impossible struggle of pulling the waist of the jeans over her ass, before they suddenly popped over the sizable obstacle and the sound of her ass cheeks clapping the top of her hamstrings upon release echoed in my ears. Just a 44 year old woman named Lisa with tanned skin, a soft layer of fat over her flat tummy, round ass and a pair of long brown legs, impossibly thick from every angle, right down to her calf muscles with not a drop of cellulite in sight. And at the top of it all, a calm, heart-shaped face with the slightest smirk of a woman seeing a familiar sight: a deeply horny, but inwardly intimidated man.

She then stepped forward and stripped me, one piece of clothing at a time, kissing my belly and nipples as she slid my shirt off, along my belt line as she undid my pants and down the v-line made by my abs as she slid off my boxers. She was only about three inches shorter than me and gently took me in her arms before rolling us onto the bed.

We were immediately on our sides, my left arm under her torso, my head laying against her right arm and her thighs wrapped around my stomach. As her thighs enveloped my body, knees bent so her heels were touching my butt, they swelled around either side of me and I felt like she was swallowing up my entire rib cage. The layer of subcutaneous fat on her thighs proved to be a thin one as a wall of firmness gripped me from either side. She snaked her left hand behind my back as her thighs gripped me. Her breasts filled my vision and I looked down to see her body sink into her waist then splay out into her almost spherical hips. I could see my well-honed, pale physique disappearing into the tight V between her tanned thighs.

Having locked me in place, she began lightly grinding against my hip as whispered in my ear. "Are you ready to have your mind blown? To be so empty, so satisfied, that you can't get it up for a couple of days? To find out what sex with a woman is actually supposed to be instead of the shallow nonsense you probably get from those young, skinny skanks in the club?"

Her teasing words had me trying to squirm with desire, but with the way she was wrapped around me I found I could barely move and instead just nodded my head as I groaned out, "Yes please."

I had never felt so helpless as she held me, resuming our make out session from before, my diamond hard penis bobbing in the air as precum streamed out steadily. After a couple minutes, she pulled back and began to relax her arms and legs from around me, making me suddenly feel alone.

"Don't worry baby, the fun is just getting started," she said with a giggle as she slid down my body to lay across my waist, wrapping her legs around my right leg and pulling my legs apart. She began to gently blow on my engorged head as she stroked and teased my balls lightly with her right hand. She would intermittently slide that hand ever so lightly up my shaft, just barely teasing the sensitive nerve endings driving me wild with desire, her left hand sliding under me to play with my taint and asshole.

The first time she tickled my sphincter I jumped and tensed with fear, eliciting another giggle. I begged her, letting her know that for me it was a one way passage and she assured me that she would never do anything I didn't want and to trust her.

This teasing seemed to go on for an eternity, pushing me ever closer to orgasm but never quite there when she finally slid her lips over my head, her tongue laving my glans as she settled in and started sucking.

I gasped and groaned with pleasure at the sudden, new sensations and instinctively pressed down on the back of her head. She forcefully pushed back, sliding her mouth off my cock and turning to look me in the eye.

"You're more than welcome to play with my hair or massage my scalp but tonight I'm sucking you dick, you're not fucking my face. Try any of that shit again and you will deeply regret it, you're very vulnerable just here, and you certainly wouldn't want my teeth involved."

As she said this, her fingers slid around the top of my scrotum, pulling my balls down enough to remind me that I was at her mercy, but not enough to hurt.

"Don't get me wrong, sometimes I like a good facefucking, and depending how tonight goes you may get to find out what it's like. But it's sort of similar to you sliding between a woman's legs and gently licking and fingering her until she explodes versus her pinning you down and grinding roughly on your face for her pleasure.There's a time and place for both, but always with both partner's consent."

Having put me in my place she went back to the task at hand, her lips and tongue working their way up and down my shaft with a practiced expertise as her fingers teased and caressed my balls, taint and inner thighs. As before, she would work me up to the edge before backing off or changing technique, keeping the pleasure pulsing throughout my body, but never taking me to the promised land.

I began to gently stroke her hair, neck and back to try to focus on something to regain some control but she just upped her game right with me, her fingers, lips, tongue and occasionally (and gently) her nails and teeth tantalizing every inch of my groin until every moment of contact with the head of my penis had me lurching and moaning with pleasure and my entire body was coated in sweat.

I knew she could keep this game going forever, that she was daring me to admit defeat and beg her and moan her name. My pride was still telling me that I should be the one in control but deep down I was beginning to accept that I was most definitely not. Just as my thighs began to cramp with her most recent attack on my sensitive tip I managed to moan out, "Lisa, please, I'm begging you!"

With that she pulled off and turned back to me again, her nails gently tracing over my corona making me twitch as she smiled lasciviously and said, "Your wish is my command!"

She promptly slid her mouth straight down onto me, all six and a half inches in her mouth as her throat muscles worked me and I exploded, rope after rope shooting into her belly as I arched off the bed. She just kept going until I felt like my balls were going to implode and managed to groan out once again, "Lisa, please, I'm begging you!"

Once again she pulled off, rolling onto my legs and rubbing her palm around my now overly sensitive glans as she said, "Was that good baby? Was that the best you ever had?"

My whole body spasmed as I pulled her hands away and said, "Damn woman, enough, you're going to send me to an early grave if you keep this up!"

She giggled again and slid back up, wrapping me up once again in her legs and arms as I came down from my post-orgasmic high, my body exhausted and drained and I was overcome with a sense of clarity.