This is a continuation of a story from a few years ago. After recently posting the story of my (first) amazing hookup with an older woman, I feel like I had to post what happened next.
Link to Part One is located here: [https://www.reddit.com/r/gonewildstories/comments/eucgx5/milf_twice_my_age_rocked_my_world_mf/?utm_source=share&utm_medium=web2x](https://www.reddit.com/r/gonewildstories/comments/eucgx5/milf_twice_my_age_rocked_my_world_mf/?utm_source=share&utm_medium=web2x)
Disclaimers: Names have been changed for obvious reasons. Actual conversations and texts are from the best of my recall.
Since this is a long story, readers can skip ahead to **The Part with Sex** if uninterested in the background and buildup. However, I promise I’ve attempted to write it to make it worth the whole read.
The cast:
Me: ‘D’ 26YO at the time, athletic white guy, about six feet tall.
Her: ‘Kari’ about 50YO, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).
The morning I left Kari’s house, she told me she’d keep my number. I wasn’t realistically expecting to hear from her again, as our respective lives could not have been more drastically different.
At twice my age, we were at such different places in life and I had no expectations of any sort of relationship with her. To quickly recap: I was heavily invested in my new job and she was on the backside of a divorce and teenagers. We had met in a bar, danced and had a pretty great one-night stand at her house.
In the weeks that followed, I went back to work and life went on as usual. Considering our night was nothing more than a great one-night stand, I pursued other romantic interests, closer to my own age. One unexpected afternoon, my phone showed a text message from Kari.
*D, I want to talk to you.*
My stomach dropped, a little, with this ‘bolt from the blue.’
*Okay, what’s up?* I asked via text.
*I was thinking about that night we met. I want to meet u again, when it’s good for us. Only something casual, no strings attached.*
Very forward. Kari knew exactly what she wanted and although I wondered about her motives or implications on my life, our one night stand had been unreal. I was honestly far too excited by the prospect of sex with her again and really taken by her directness.
*I had an incredible time, too. I’ll be in touch- that sounds like fun.* Was my reply.
Throughout the next work week, we traded a few texts, some fairly suggestive.
*excited to see you soon* I sent to Kari one evening, leaving the gym.
She replied: *me too* *hopefully as fun as last time;)*
One night, going to bed, my phone chimed with her message: *looking forward to you*
I replied, *can’t wait- let me know when* She got me thinking again, writing *my place isn’t going to work for a while* I thought about it before writing and ultimately responding- *how about we get a room somewhere?* Kari replied *That sounds fucking hot. I’m going to touch myself before then ;-)* She’d started to get me hard just via text. I wrote back *now I’m going to have trouble sleeping!* I can only image the look on her face when I received her simple reply: *Good.*
Later on, while I was at work, I simply got her text- *Can’t wait to put my mouth around you again.*
Holy shit. Was I a sucker for that.
Another week or so went by, and, sitting at my apartment, drinking a beer late on a Saturday evening, my phone chimed- Kari. I had wondered why she had waited until so late to text, but then tried not to overthink it.
*Hey, D last minute but I’m hoping ur free tonight?*
*yeah, for you I’ll make time*
*u gonna get a hotel?*
*So I have you all to myself then*
*;)*
Overeager at the prospect of some hotel sex (the best kind, in my humble opinion), I got online and booked a room close to where we were planning to meet up.
I quickly took a shower, grabbed a few condoms and headed out to a local bar to go meet her.
After arriving at the bar, I grabbed a seat and drinks for both of us. She arrived soon after. It had been some time, so I’d almost forgotten what she looked like. But she’d come to impress. Like the last first time we met, I unashamedly checked her out, which she noticed, with a satisfied grin. She was wearing a short and pretty green dress with tan heels. She still looked stunning, she obviously managed to spend some at the gym and in the sun, as her petite frame had sexy muscle tone and a great suntan. As she sat down and grabbed her drink, I noticed her green painted fingernails (which had to do with something she’d save for later). We exchanged a chaste kiss on the cheek and made small talk until that bar began to close.
“Let’s move on to somewhere else,” Kari suggested.
At the next crowded pub, we stood at the edge of an overcrowded bar and ordered drinks. We spoke loudly, our faces only inches from each other. Kari kept a real intensity to her green eyes that I found completely magnetic.
“So, you know I don’t have any intention of taking this any farther, right?” Kari asked me.
Ice in my gut. Or more accurately, ice on my crotch.
“Yeah, I had a feeling that was where we were at. We’re in such separate places,” I admitted. Maybe this was a bad idea, after all.
“You’ve got your life, I’ve got mine. I’ve got some things going on that make this tricky.” I assumed she was alluding to her divorce and teenagers.
“Yeah, I’m okay with not taking this further” I replied. Damn, I was really excited with the prospect of hooking up again. Which seemed to be fading fast.
We ordered and drank another round. We made small talk about her fitness, favorite kinds of local beer and other bars we tried and enjoyed.
Probably sensing me deflate a little, she added: “You know I am still going to go back to the room with you. I hope you got one.” She playfully leaned toward me and nudged her hips into my crotch. As we drank, she suggested a round of shots. After we drank those, she discreetly grabbed my hand and took it to her ass. I happily squeezed her soft but firm backside and again, felt the hint of a thong underneath that green dress. The night was seeming promising again.
More drinks followed. More flirting and not-so subtle touching came with it. Now a little tipsy after a couple of shots and beer, we called for a cab back to the hotel I’d booked a room at. In the taxi, a minivan, we sat in the second-row seats, separated by a few feet. She reached over and felt the bulge in my jeans and played with my balls, quickly and effortlessly getting me hard. I ached to fuck her and returned the favor, rubbing her pussy through her lacy panties. Between her legs was deliciously wet. I couldn’t wait to jump out of that damn van. Maybe the longest taxi ride of my life.
Arriving at the hotel lobby, I checked into the room, while Kari stood with me, tapping text messages away on her phone. I had a fleeting thought where I wondered whom she was texting. I got the room keys and we took the elevator up to our floor.
“That guy really was giving us a sideways look, wasn’t he?” Kari asked about the employee working the front desk.
“What, like we were about to go upstairs and make some bad decisions?”
“That’s the look. And he’s so right.”
We exchanged a little smile.
The elevator dinged and I put my arm around her petite waist and walked to our room.
**The Part with Sex**
We entered the room and she excused herself to the bathroom. I turned on a few lights and drew the curtains. After I emerged from the bathroom as well, I found Kari with her hand on her hip and a sly grin across her face. We finally met aside the bed and embraced.
We made out and even before I could remove my dress shirt, Kari had knelt in front of me. I removed my belt and she quickly grabbed the waistband of my athletic underwear, letting my erection ‘pop’ free, grazing her face. She pushed my dick upward and took a long, slow lick of me, starting with my balls and licking along the whole shaft. Kari maintained eye contact the entire time. The blowjob was slow and hot as hell. She took her time, licking, kissing, at one point, even playfully slapping the tip of my cock against her tongue. She stared intensely at me, with her radiant green eyes. I enjoyed every second and I knew a part of her did, too.
“You’re really fucking good at this,” was all I could manage.
Kari, smiled, spit on my cock and stroked the underside of it with her green nail painted fingertips. “Mmm-hmm, wasn’t lying when I said I wanted my mouth on you.” She took me in her mouth again and moaned with me in her mouth. Holy fucking shit. Her intensity went to another level, she looked almost angry, as she worked me quickly. At to the point where I couldn’t take it anymore, I told her “holy fuck, I’m gonna cum if you don’t stop.” “Go sit in that chair,” I instructed, pointing to the hotel room chair.
She sat down, spread her legs and lifted the bottom of her dress, revealing a cute, bright green lacy thong. I knelt in front of her, my hands caressing the inside of her thighs.
“Those are really cute,” I told her, savoring the view of her wet thong. “My fingernails match,” she said. I noticed that her green thong matched the color of her painted fingernails. “See?” She asked, tracing her fingertips across her pussy lips.
I had been aching to eat her pussy since the last time. I started with some kisses and licks in the inside of her thighs. I moved over to her lips and did the same there, finally pushing aside her lacy green thong. I gave her long, wet licks from her asshole up to her clit and back again. I took time to suck on her clit and easily slid my fingers inside her wetness. I kept pressure on her clit with my tongue, while I played with her from the inside with my two fingers. Hearing her whimper and moan made it almost impossible to stop. She pulled me close to her, grabbing the back of my head.
Eventually, I let up and grabbed a condom from my jeans. Kari moved herself to the leather ottoman in front of the chair and started taking off her panties.
With one hand, I aggressively pulled off her thong, probably getting close to tearing it. “Easy there, I know you want this,” Kari cautioned. With my condom on, I teased her clit briefly and slid into her warm pussy. It was reminiscent of the first time we’d had sex; her in her heels, me crouched over her, fucking her. She dug her heels into my back. I held onto her hips and just thrust, hard and deep.
After a while, I offered: “let’s switch it up.” Kari stood and removed her dress, revealing a lacy green bra, which also matched the thong I’d previously almost torn off. Her dress bunched up around her ankles; I’d not noticed a delicate tattoo on her ankle until now. I still marveled at her tanned and toned petite body, stretch marks and all. Still wearing her heels, she went to the rooms’ desk and bent over it, sticking her ass out for me. “Come take me over this desk now.”
I happily complied, entering her from behind. This time, feeling more empowered, I grabbed her hip and the back of her neck as I started to increase the pace. Starting to sweat, I stopped to fully take off my dress shirt and undershirt. I could sense Kari was getting impatient, me inside her and not moving, she looked over her shoulder, with an impatient stare. I slapped her ass. Once, then twice, harder and she made me melt with a little whimper as I continued to slide into her.
“I want to show you my favorite way,” Kari breathed. I pulled out of her, stealing a look at her sweaty, toned ass and my swollen, glistening dick. Taking advantage of the pause, I finally took off my sweaty shirt.
While I was taking off my shirt and taking a breather, she’d been busy. Kari was completely nude (heels off, too), on all fours, facing away from me. She’d torn the comforter from the bed and I enjoyed the sight of the contrast of her warm, tanned skin against the soft white sheets. Again, she rounded her back, so her ass stuck out towards me. Those sexy little tattoos on her were calling out to me. Shooting me a ‘come hither’ look over her left shoulder, she asked “you coming or what?”
“Damn, I’m gonna cum in no time at all,” I half-joked. I got on the bed on my knees behind her and entered her. The only way I can describe what happened next is that we FUCKED. And we fucked hard and fast.
In a half-drunken blur, I remember bits and pieces. She pressed her ass back against me. I grabbed her shoulders, her neck, her thighs. I slapped her ass a few times, enjoying her moans as I did so. She slapped her own ass. I reached forward and grabbed her small breasts with the hard and perky dark nipples. Kari reached back and pulled my ass in closer to her, digging in her nails. I put my hands on her arched and toned lower back. I grunted. She moaned in vowels. She and I took turns grabbing handfuls of pillows and sheets. She tensed up then moaned an explosive “mmmmmm!” with what I assumed was her orgasm. Hearing that was a point of no return and I came hard in the condom inside her. I continued to thrust into her, as my cock pulsed. On my shaking knees, I finally pulled out of her and removed the filled condom.
I laid on the messed bed beside her. Kari smiled a big grin, her hair frazzled. Instead of kissing me, she told me “you still smell really fucking good.” I laughed and she kissed me, then quickly tracing her tongue down my neck to my shoulder blades. She straddled my knee and took my cock in her hand, giving me a few slow strokes as she licked and kissed my chest.
“I’m really glad we did this” Kari said, her voice husky.
Our heavy breathing filled the silence. I collapsed next to her, nuzzling my face in her tousled sandy hair. We kissed, deeply again and the room spinning around me, both quickly fell asleep.
I am working on Part Three, our conclusion, which will be much shorter than one or two.
Source: reddit.com/r/gonewildstories/comments/f0yh1z/milf_rocks_my_world_again_mf
Fucking loved it