This is a true story from a few years ago. I’d never been with a older woman before (or since, I suppose) who’d been as sexually confident and assertive.
Disclaimers: Names changed for fairly obvious reasons. Additionally, readers can **skip to the marked foreplay and sex parts** below, as this is a fairly long story.
Your cast:
Me: ‘D’ Six feet tall, 26YO at the time, athletic white guy.
Her: ‘Kari’ about 50YO, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).
It started at a local bar. I’d just gotten off a long week of work and was simply intending to eat dinner and head home for some needed rest. As I was finishing my beer for the night, an older woman and her friend sat down beside me.
I did an awkward and probably very obvious attempt to pretend like I wasn’t checking her out. She had a wonderful sundress and heels and I was really drawn to her sleek shoulders and toned, tanned legs.
She smiled at me and asked if she could sit down.
“Sure” I replied, nervous that our only interaction thus far was way too creepy.
After a short minute, she turned to me and said” I’m Kari, by the way, and this is my friend.” “You didn’t ask!” She added.
We struck up some small talk and I ended up staying way longer than my beer and dinner. She was quite a bit older than me in age and life experience (teenage kids and divorced). Certainly not the type of woman that I would have sought out to date, but I was really drawn in to her strength and confidence. (Not to mention, obviously, she was quite attractive).
She said that she and her friend were going dancing and asked if I’d want to join her at a local nightclub. I figured, why the hell not and unhesitatingly traded phone numbers.
On the way there, I texted her and told I was on the way.
Nothing.
Maybe she was just toying with me. It was getting too late in the night to play any games.
I arrive and parked and texted her again. Nothing. Not a good sign.
I reluctantly walked up to the door, and spent a few minutes scanning the crowd. As I was turning around, about to walk away, I head a shout- “D!” “There you are!”
She ran up to me, with a (strong) drink with two cocktail straws. “I got your texts and got us a drink to share”. She pulled me in for a close hug and a kiss on my cheek. Her body was firm, but soft against mine and I may have almost been blushing with her more intimate gesture.
“I’m really glad you showed up” Kari said.
We sipped the same drink for a few minutes and I asked her if she wanted to dance, which she did.
We moved out to the floor and quickly got to know each other much better. With the music booming and packed into the dance floor, we got close and hot. My hands caressed her tight back, then her hips and
I stole a feel below her hip and felt the hint of her thong. Her hands explored my chest, shoulders and the inside of my thighs. I tried to position myself so she couldn’t feel me get hard, but I’m certain she did.
**some foreplay**
After the club began to dwindle and a country band took the stage, she pulled me in close behind her. I could feel the warmth of her hair and sweat on our bodies. “I never do this, but lets get out of here,” Kari breathed into my ear.
As I drove, we made innocuous small talk as she gave me directions to her house.
I rested my hand on her smooth and toned leg. During the drive, I let my hand wander to the inside of her thigh and above. I brushed my fingers along the outside of her panties, which were warm and wet. She let out a small, stifled whimper as I increased pressure. I increased my pace and rubbed her clit in small circles. I’ll be honest, as almost theatrical as her whimpering might have been, it felt great to hear.
“Oh shit- you’re gonna miss the exit!” She exclaimed. “Turn here.”
I put both my hands back on the wheel and turned off the highway. Kari took advantage of an opening and put her hand confidently in my lap. Unlike where I had started slowly, she quickly massaged my jeans until she found the head of my penis. She moaned (probably a little fake, in hindsight) as she rubbed me, but nevertheless, a huge turn-on. We approached her street and she had just unzipped my jeans, I felt her fingers graze along me, her hand wet with a little pre-cum.
I pulled the car into the driveway and zipped my jeans back up. “Are we expecting any company tonight?” I asked, now nervously remembering the murky details about her divorce and teenagers.
“No, it’ll just be you and me here” she assured me.
We entered her house and went straight for the kitchen where we drank bottles of water. Unlike the club or the car, she physically distanced herself from me, which was off putting.
After a long pensive silence, she asked if I “wanted the tour?”
I agreed and I followed her through the living room and we stopped at her bedroom. (The room was immaculate, the bed was made, there was a couch at the foot of the bed and a large mirror in front of the closets- more on that soon!)
“That’s the only stop on the tour.” Kari boldly said.
“Short tour?” I replied.
“Well, D, you have been making me wait for it all night.”
“Let’s not waste any more time then.”
**The part with the sex**
She stepped in close to me and we kissed. I kissed gently at first, then she pulled me close and our tongues met, kissing more urgently. She whispered in my ear “you smell really sexy.” My fingers traced her sundress’s shoulder straps and I slid them down her shoulders, kissing her shoulder blades and neck. “Mmm-hmm” she encouraged.
In a mood-killing move, I grabbed the bottom of her dress and tried to pull it over her head. It didn’t work- her dress got stuck around her waist. Kari laughed at me and said “just let me do it!”
“Thanks,” I laughed as she unzipped her dress and slid it off. Still wearing those dynamite heels, she stepped out of her dress, revealing a silky white thong and matching strapless bra. An old c-section scar and some stretch marks were visible and sexy as hell on her toned body. I was surprised and delighted as she had a large and really sexy series of delicate tattoos encircling her midriff and hips.
We kissed again as she unbuttoned my dress shirt, kissing (and licking!) my chest. Now, the mirror- She turned (quite intentionally, I’m confident) so her backside was facing the mirror, giving me an incredible view of my hand on her ass and her heels.
I unhooked her strapless bra, flung it to the side and felt her hard, dark nipples. She softly moaned as I touched her small breasts and played with her nipples.
Her hands traveled down my chest, through the hair on my stomach. She got frustrated with my belt and “a little help, please,” she smiled. I unfastened my belt buckle and unzipped my jeans, letting them fall to the floor. We continued to make out and her hands traveled on either side of my erection, caressing around, brushing softly against, but never quite touching it. I was rock hard and it was agony that she kept teasing me.
Sensing a cue, I grabbed her by the waist and led her to the couch in front of her bed. I sat down on the couch and she didn’t skip a beat. She sat next to me and draped her leg over mine, finally grabbing my erection and freeing it from my boxer briefs. She leaned over and took me in her warm mouth as I took off my socks.
We laughed again, and she asked me to just lean back. I took off my underwear and my now wet cock throbbed as she kneeled on the floor between my legs. She arched her back and, in the mirror, I got the most incredible view of her ass and now-barely covered pussy.
Kari looked me in the eyes (one of my favorite all-time moves) and began to give a to-die-for blowjob. It was wet and never too fast. Her technique was incredible as she teased the tip and used her lips, kissing the underside of my shaft.
I leaned forward and gently grabbed her hair and shoulders. After I was on the verge of exploding, I told her it was my turn. She didn’t miss the cue and traded places with me, spreading her legs wide and pushing her wet thong aside to show me her waxed pussy.
I sat on her floor in front of her and enthusiastically licked and teased her. (She cums first, after all!) I played with her clit with one hand and inserted two fingers from the other in her. All the while, she gripped onto the back of my head, pulling at my hair. Listening to her moan and gasp was incredible.
I got up to my knees between her legs and watched her finger herself while I put on a condom. I pulled off her thong and teased her clit the tip of my penis, listening to her moan and watching her squirm. Not waste any more time, I entered her. We fucked for a short time, both working up a small sweat. “Oh my goddddd,” she moaned. She held her cute, small breasts as we fucked. She pulled me in close and wrapped her legs around me. I stood up into almost a half crouch and thrusted fast and aggressively now. Her high heels dug into my back. “Don’t stop, you’re making this so good,” she breathed. Listening to her moan, I couldn’t contain myself any more and came way too quickly, continuing to thrust as I filled the condom inside her.
Exhausted, I pulled out of her and laid on the couch next to Kari, who squeezed the condom empty and dripped my cum onto me, which she slowly licked off. I literally have never been as speechless as when she then put my cum-dripping cock in her mouth and quite literally, sucked me dry. No woman I’d been with to that point had been so fearless when it came to my cum.
She kept working me in her mouth until, inevitably, I softened. She had seemed to thrive on my squirms and toe-curling moans while she worked me. “God, you are fun to play with,” she said. We held each other on the couch and she lightly dozed.
As the sun was starting to rise, we awoke and I got dressed. The sight of her backside, walking naked to get a robe is one I won’t forget. I was speechless at her toned ass and those little sexy tattoos on her hips. We kissed on the way out the door and I told her I was speechless and had an incredible and unexpected night. Kari replied: “I had fun, I’m going to keep your number.”
Will post the stories of our next and final rendezvous soon.
Comments and Messages are always welcome!
Source: reddit.com/r/gonewildstories/comments/ehxjhv/milf_one_night_stand_twice_my_age_twice_as_fun
Great writing dude!