Online Adventures Vol. 02: Kimmy

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Our protagonist has a HOT night with a cougar.
5.7k words
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Part 2 of the 5 part series

Updated 06/09/2023
Created 08/06/2019
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Jay1415
Jay1415
30 Followers

Greetings readers!

Two years ago (shortly after my 30th birthday), I got out of a (too) long relationship with my ex girlfriend Amanda. I had spent the better part of my twenties with her. There were plenty of good times, but as the years went on, our sex life became less and less eventful. Sadly, it wasn't particularly eventful to begin with. When we ultimately broke up, it took a few weeks for me to get my head (and the whirlpool of emotions spinning around therein) back on track. With Amanda in the rearview, I had realized that I had YEARS of good sex to catch up on. In particular, I realized that it wasn't just sex I was looking for but some reasonably light kink, intrigue, adventure- something different from the vanilla I'd been living with for nearly a decade.

I had discovered the personals section of a popular online classifieds while selling a guitar Amanda had bought me a few birthdays back. Out with the old, I figured. For anyone who's ever browsed this section of the classifieds, you know there is quite a range of listings. Some with photos, some that get right to it, some a little less aggressive. I had never been on an online date but as I had been in the market for a little excitement and intrigue, Online personals seemed like a good place to start. As a New Yorker, there was no shortage of listings.

In the two years which followed my breakup from Amanda, I met approximately 15 different women of various backgrounds and ages (ranging from 27-58). I discovered a lot about myself during these encounters, particularly that I have a seemingly bottomless appetite for BBW.

What follows are true accounts of my favorite encounters with 8 of these women. Names and certain details have been changed, but the plot of each of these stories is accurate or VERY close. I hope you all have as much fun reading these accounts as I had writing them. Enjoy!

Volume 2: Kimmy

"Cougar seeks cub!"

My previous experience with 41-year old Monica left me with a delightful taste in my mouth when it came to older women, so when Cougar Kimmy emailed me back after sending a very carefully crafted message to her, I was pretty stoked.

Kim (or Kimmy as she insisted I call her) seemed to be in her late 40's, maybe early 50's but I didn't find it polite to ask. If she wanted to tell me, she would. We exchanged the customary photos and she got right to it with two topless pics.

Kimmy was SUCH a MILF. Average height, perfectly overweight, DD cup breasts (she told me the size) with a very round ass. My favorite thing about her (so far at least) was her face. There was no other way to say it. She simply had a VERY beautiful face. She looked a bit like Vanna White, I had thought. In her photos, she was always smiling (which intrigued me about who was taking these photos for her) but as far as I was concerned, she was she was smiling at me.

We started exchanging emails on a Monday evening, texting by Tuesday and the plan was for me to come up to her townhouse in southern Connecticut on Friday night, assuming we were still into each other by the weekend.

Kimmy seemed pretty cool. Former hippie, very into classic rock, The Grateful Dead in particular, and music of that genre.

"Maybe we'll throw on some Dead, roll an enormous joint and dance around my house naked like it was Woodstock" she had suggested in one of our conversations.

None of that sounded like a bad idea to me. We chatted about our interests, likes and dislikes. Kimmy wasn't into anything outlandish.

"If it feels good, and we're both comfortable, go with it" she spoke like a true flower child I thought.

Kimmy seemed super chill, as most Deadheads tend to be and that put me at ease. I was done with uptight bitches like my ex girlfriend. Kimmy seemed like anything but.

I'm definitely not a dick-pic kinda guy but since she opened with some sexy shots, I sent her a photo of my cock at it's hardest.

"Such a BIG boy" she texted back."Friday can't get here soon enough," I replied with an emoji kissy face. Sending the photo was hot. Made me feel a bit sleezy. But maybe that's what my life was missing...

Kimmy and I stayed in pretty consistent contact via text, keeping the energy going, which made an otherwise stressful week of work, way better.

A very pleasant distraction. She'd text me during work asking me how it was going. And when I hit her with the sad face or angry face emoji, she'd reply with something like: "Remember Jay, Woodstock is only a couple of days away." I knew what that meant and by Friday morning, I was beyond stressed out and in need of something to take my mind off work.

"Tonight's the night!" I texted her.

"You ready for our playdate?"

"Never been more ready. I've even been listening to The Grateful Dead all week!" I replied. She liked that.

She texted me her address and suggested I take Metro North up to her station in lower CT. From there I could walk to her house or she could pick me up. I didn't want to put her out, so I told her I'd walk from the station, and hopefully arrive by 8.

"Oh, one more thing hun" she texted before we ended the conversation. "I'm not like those young bitches you're probably used to."

I already knew this, of course, by now. I tried to say something flattering. "Oh I know, you seem way cooler."

"Thanks babe, but there's something else, which doesn't always jive with everyone... I have a big fat bush that I am VERY proud of..."

I wasn't surprised to hear this. She was a 60's/70's flower child through and through it seemed. And she was right about what I was used to. Most women I had been with were somewhere between completely shaven and very nicely trimmed. I was SO into Kimmy at this point that if her hairy pussy were a problem for me, it didn't register at the moment. My mantra throughout this whole online dating thing was that I could walk anytime I wanted, so let's roll the dice on Kimmy's "big fat bush" (as she so delightfully referred to it).

I thought to myself as I responded to her text with something along the lines of: "Oh yeah? Well if you're so proud of it, I can't wait to see you strut yourself and show if off for me tonight."

"My my Jay, you have all the right answers. Don'tcha?. See you at 8"

"Can't wait, Kimmy."

After a quick shower, the usual grooming and a quick strut in the mirror, I was out the door and on my way to the train. I grabbed an express train, which still took an hour. I hadn't taken the train to Connecticut before and was pleasantly surprised to see that this particular line had a bar car because I definitely could use a drink at this point. I purchased a tallboy and nursed it the entire way there, arriving just before 8pm.

I took out my phone and began following the directions Kimmy had provided me to her house.

At just after 8:15, I rounded her corner and found the house. "I'm here" I texted her. Just as I stepped up to the front door, she opened it.

"Jay!" Kimmy said, throwing open her screen door.

"Kimmy!" I replied, trying to mimic her excitement.

We kissed minimally on the lips as she brought me inside. Immediately, I could smell that Kimmy had gotten started with her little pot party before I got there.

"Smells good in here" I said with a smile.

Kimmy was wearing a silk robe/kimono type thing which made its way down almost to her knees. I could see her big thighs, which led down to a very nice set of legs (which I was very glad to see were shaved, considering I knew what was waiting for me under that robe) and a very impressive bust line.

"Hi there" I said, trying to sound innocent. I knew the young, innocent, naive thing drove her wild so I kept that in mind as I went on.

"It's so nice to meet you Kimmy. Thank you for inviting me over"

"Well you're sweet for coming" she replied, smiling. "I've been looking forward to having you over all week. Won'tchu come in?"

Kimmy took me by the hand and walked me into the living room, which I noticed looked like it hadn't been redone in quite some time. It wasn't straight out of the 70's but it was close. Kimmy picked up a remote, hit play and on came The Dead. Kimmy turned down the volume. "I want us to be able to talk and communicate. I'll turn it up later" she said, sitting us down on her loveseat.

"Sounds good to me" I said. I took a deep breath. I had a feeling things were about to kick into gear.

"Now, I have been waiting to kiss you alllllll week Kimmy, so may I?" I asked as shyly and adorably as I could muster.

With that, Kimmy leaned in and we locked lips. Our tongues met in the middle and licked as we both groaned and sighed. Our lips parted slowly, but our tongues kept going at it, licking each other. When we stopped, we smiled at each other. Without a word, Kimmy stood up, walked a few feet away and with her back to me, undid the silk rope on her silk robe. It dropped to the floor and I got a great look at her ass. Big and round as pictured.

"Like what'cha see Jay?"

"You know I do, Kimmy."

Kimmy turned around and there it was. Her DD breasts in full view, definitely more on the saggy side than perky side, big areolas and nice long nipples, not fat, but long and slender. The true hero, however, of Kimmy's birthday suit was indeed her big fat bush hanging between her legs.

"Ta da!!" she said, striking a pose, her arms up and out like a gymnast who just stuck the landing. She did in fact seem to be proud of it.

"Kimmy!! You are so beautiful. And your big fat bush- I WANT it..." At least I thought I did, I thought to myself. Who knew? It might not be as pleasant as I was fantasizing about, but I'd probably find out soon enough."

"It's OUR bush" she replied. "And just so you don't worry, I keep it VERY clean every single day".

"Well that's very good Kimmy." I said smiling. "I guess it's my turn for the ta-da moment."

I continued as I stood up, unbuttoned my pants, took off my shirt and stood there in my boxers while Kimmy watched me, with this predatory look in her eye. Following her lead, I turned around and dropped my boxers.

"Look at that tight ass...ooooooohhhhh" she exclaimed. I have a surprise for you as well Kimmy."

She had seen a photo of my cock, so this wouldn't be anything new, but she didn't know about my low-hanging balls so this would be interesting.

I turned around quickly and showed it all.

"Ta da!" I said jumping into that same pose as she did.

"O.M.G." was all she could say. "Baby, those are grown man balls. Bull balls." Where the FUCK did you get those?!" she asked, her mouth wide open in astonishment.

"Who cares I replied. Fun fact though, about them... they're YOURS. These are YOUR balls." I said with authority. She stood there slack-jawed as her smile began to widen.

"Now I thought I smelled some weed. Let's have some fun" I went on.

Kimmy laughed.

She went into the kitchen and came out with an ashtray and an enormous joint, some of which she had already smoked. Kimmy lit the joint as we stood naked in her living room. I can't say I've ever stood naked and smoked a joint, but it was VERY liberating. We sat back down on the couch passing the joint back and forth, touching and caressing each other. While Kimmy had the joint, I'd be playing with her tits. When I had the joint, her hands were everywhere.

We put the joint out halfway. "How ya feelin?" she asked, looking me in the eye.

"Never better" I replied with a grin.

"I was thinkin'" she said. "Why don't I throw down a bunch of blankets and pillows on the floor here and make us a little playpen of sorts?"

"THAT sounds like a great idea" I replied with enthusiasm.

Kimmy went to a hallway closet and came back with a HUGE handful of blankets and pillows. We spread them out on the floor and it was actually quite soft. In all, we had 3 blankets atop one another and half a dozen big bed pillows and each of the throw pillows from her couches. When this was all done, Kimmy turned the music back up and invited me over.

"Come play with me, Jay". She got on her knees in the middle of the blankets. And motioned for me to join. I walked right over to her. She took my scrotum in one hand and my cock in the other.

"I've been waiting all week to suck your dick" she said as she took my fat mushroom head in her mouth. She let out a huge throaty groan as she did it. She began taking inch after inch, but not the whole thing, indulging as she went. I could feel my tip against the back of her throat, as she massaged my balls and scrotum with both hands, taking the occasional break to squeeze my asscheeks with both hands.

This was a GOOD blowjob. Very wet, very slow, rhythmic, hands everywhere. My hands were rubbing her head, scratching her shoulders, her ears, her cheeks. I moaned and made noises to let her know how much I was enjoying this.

"Baby, you are too good to me. Slow down before I cum down your throat." I said to her, as she showed zero signs of caring about my plight. I wasn't ready to cum yet either. And if she were going to suck me to orgasm, I wanted her cunt in my mouth while it was happening.

"Can I taste your pussy please baby? I neeeeed it. Please baby don't suck me over the edge just yet. Pleeeease" I said in the sexiest way I could think of.

Kimmy stood up and stuck her tongue down my throat. "You wanna taste my pussy, Jay? You ready for my big fat bush, baby? OUR big fat bush, baby?"

She sat on the floor and spread her legs wide for me. "Eat up baby" she said, looking right into my eyes with that same predatory look she gave me earlier.

I crawled over to her, grabbing her by both ankles, spreading her legs wide. I brought my face down to her bush and inhaled through my mouth and nose. Her pussy smelled intoxicating and there was something primal (or maybe even tribal?) about Kimmy's hairy pussy. With her legs still spread wide, I stuck out my tongue and found her clit. I gave it a lick and Kimmy lost it...

"Ohhuhhhhhhhuhuhhhh" she wailed, after just one lick.

As I held her ankles, I continued to lick her clit and suck on it intermittently. Her bush wasn't making it easy to eat her pussy, but it was different. And the fact that Kimmy was so proud of it was even sexier. Kimmy moaned and groaned and squeaked as I ate her out. I put her legs down and scratched her thighs as I tongued her cunt.

"Kimmy. Your cunt is delicious, I garbled, barely able to make out the words.

"Mmmmmmm... Eat it baby." Kimmy did in fact taste great. I wanted more.

"I think we absolutely need to 69 right now baby. What are your thoughts baby?" I suggested, looking up from her pussy. "Why don't you get on top of me and stuff your big, beautiful bush in my mouth while you suck my dick till I nut? I promise I'll eat your pussy so good Kimmy, I promise". I winked at her and gave her those eyes I knew she liked so much.

"You're so fucking hot Jay. I swear" She said getting on her knees as I lied down on the blankets.

Kimmy spun around and put her leg over my face and settled in right on top of me, immediately taking my cock into her mouth. Back on my end, I was IN it. My face between her thighs, her big fat ass just above me and her bush stuffed in my mouth. This was fucking raunchy. I found her cunt and began sucking on her pussy lips. I sucked her clit as I grabbed her by the asscheeks and squeezed. This made her pussy noticably wetter.

I made my tongue as rigid as possible and began tonguefucking her wet pussy. With my hands squeezing her ass, I pulled her to my tongue until I was inches inside. Her cunt tasted even better as she was nearing orgasm. I licked a finger and began rubbing her asshole.

She let out such an "ohhhhhhhhuuhhhhhuhh" when I did this that I knew this was gonna be her ticket to a memorable orgasm. After rubbing her tight butthole for a minute, I had to taste her ass. I licked my fingers. The taste of her cunt and butthole on my lips drove me into high gear. I was SO. Fucking. Turned. On.

With my finger back on her butthole and my tongue inches deep in her hairy pussy, she was squirming and squeaking and seconds from bursting. She grinded her bush and pussy harder and harder against my tongue, all the while slurping away furiously on my dong. I wasn't focused on me though. I wanted her to explode.

"Uhhhhhohhhhohhhhohhhhh" she grumbled, my cock still occupying most of her mouth. "Heeeeerrreee it comes Jay...oooohhuhuhuhuhuhuhuhuh"

When I felt her about to climax, I slid my finger into her ass and my tongue as deep into her slit as I could get it. She bucked, forcing her pussy onto my tongue as best as she could and she screamed in ecstacy.

"AAAAAAHHHHHHHAHAH HHHHHOOHHOHOHHHH". She stopped sucking my cock to manage and embrace her orgasm, as she sprayed my face, none of which I could catch in my mouth because of the rigid tongue fucking mission I was near completing. My face took the brunt of it. Having not cum yet, myself, this only sent me into a further frenzy. I kept eating her pussy and rubbing her hole as she came down from her orgasm.

"Well, Jay" she said, still on top of me, her still bush in my face "THAT was special. Such a dirty boy too, playing with my asshole...mmmmmmmmm."

"Glad you enjoyed it. But the pleasure was all mine, Kimmy".

This obviously wasn't true, evidenced by the monster nut she just busted in my face, but a lot of the pleasure WAS mine. The smells and tastes and textures of being buried in Kimmy's womanhood was unlike anything I had ever experienced. And I was hungry for more.

"Do I get the pleasure of eating your asshole too, Kimmy? Pretty please?" I asked her innocently.

"Oooh you dirty boy... how do you want it?"

"I'm gonna sit up, with my back against the sofa. Why don't you come around, stand in front of me, bend over and grind your hole on my tongue and feel free to jerk my dick till I cum everywhere."

"My my, baby" she replied. "You really do love to use that tongue of yours. Where did I find you?"

"I aim to please" I said smiling as Kimmy got up off me. I could see her bush was wet with her lady nut. God, that was hot.

Before I got into my sitting position, I crawled over to her on all fours. Very slowly, making eyes at her.

"Wha- what are you doing?" she asked playfully? "I'm comin' for that bush baby. I wanna put my face in it some more. I mean- I NEED to put my face in it some more. Right now." I got on my knees and buried my face in her hairy mound.

"Sweet baby" she said, putting her hands on my head, as I playfully licked and lapped at whatever I could. "I'm so glad you like my big bush" she went on. "Remember, it's OUR bush to play with, OURS to enjoy."

"It's magnificent, Kimmy. I'm so lucky to have such a beautiful woman with such a perfectly hairy pussy in my life." I knew she loved the compliments. And I meant them.

I sat back against the couch. "You wanna taste my ass, Jay? She said sexily.

"Feed me." was my reply.

She approached me, turned around and bent over. I reclined just a bit so we could both get comfy. She guided her hole to my mouth. I grabbed her thighs to guide her, and just like that, my tongue was on her hole. Her hand found my cock and she started stroking away as she grinded her hole against my lips and tongue. As if her pussy wasn't delicious enough, her asshole had my tastebuds ablaze. Earthy, musky, sweaty, and of course just a bit hairy. Her hole and the surrounding skin had a delightful texture- puckered, wrinkly, tight. I grabbed her by the cheeks aggressively and spread wide. I kissed her asshole with wet lips and gave her big broad licks as she cooed and continued to jack my dick.

"Your asshole tastes SO fucking good baby." was all I could say.

"It's all yours, Jay"

"Yeah? Well in that case, maybe I should put my tongue up your ass RIGHT FUCKING NOW" I said to her.

Jay1415
Jay1415
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