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Journey to 100 Women: Brian's Sexcapades (Part 16 - Michelle) [M25/F52] [Petite] [Cougar]
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xWriterofPassionx is in cougar
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This story is about Michelle, the 31st woman I slept with, and one of the wildest experiences I've ever had.

I mentioned a few stories ago that I had a coworker/friend named Lisa who ended up being a great wingwoman for me, and ultimately helped me hook up with 5 different women. Kathy (a previous story) was the first, Michelle was the second.

As I stated before, my relationship with Lisa was strictly platonic, but she got a kick out of hearing about my wild sex stories, and it was cool to have someone to talk to about this stuff without judgment or jealousy of any kind. She also enjoyed doing her part in helping make some of those stories possible.

It was the first week in June, and Lisa had asked me if I was interested in camping with her husband, her sister, and her friend Michelle.

Michelle was a 52-year-old, petite (5'1) yoga instructor, with curly brown hair and dark brown eyes.

The old me - the shy, inexperienced me, would've been intimidated by the age gap alone, but since I had already experienced fucking someone that much older than me, it didn't phase me at all. The experience I had with Kathy (who was 48 to my 23) really was a life changing event in a lot of ways.

I wasn't an outdoorsy person, and it was my first time camping, but of course I agreed to go.

We met up, and there she was - pink sports bra, black leggings, and her thick, curly hair in a messy bun.

"Ahh. The famous Brian," she said, as we were introduced to each other. "Lisa's told me all about you..."

I turned my attention to a smirking Lisa. I had given her the okay to share my stories with whoever she wanted to, seeing as how they could only help me when it came to attracting women.

"She did huh? Ha. Hopefully they were good things."

"Oh, they were," she teased.

It's a different world when you have a woman vouch for you. I've slept with several women just because a friend of theirs had already put in a good word for me. I could tell immediately that Michelle was interested, I just had to play it cool the rest of the way.

The day went on, and our chemistry was palpable. She'd go out of her way to compliment me, and our banter would turn flirtatious quickly.

"You sure this is your first time hiking? You've got a lot of stamina."

"Haha, thanks. Just trying to keep up with you."

"Oh, I think you could keep up with me..."

By the end of the day, it was clear we were into each other. As we sat around the campfire stargazing before heading to sleep, she curled up beside me and whispered in my ear.

"Leave your tent open."

We had three tents. One for Lisa and her husband, one for her sister and Michelle, and one for me.

I knew things were going well, but I honestly didn't think we'd be doing anything right then and there. I thought at best, we'd exchange numbers, and I'd follow up with her after the trip. We were dirty and sweaty from camping all day, and I didn't think she'd be interested in doing anything - but here we were, a woman almost thirty years older than me, telling me to expect a visit from her later that night.

We went back to our tents around midnight, but it wasn't until around 2am when - true to her word - Michelle quietly snuck into my tent, holding a finger to her lips.

She crawled towards me slowly and sat on top of me.

"Now...the real fun starts," she whispered, as she reached down and rubbed my crotch.

I nibbled her neck softly and we began whispering dirty shit to each other in between kisses. I had just met her less than 12 hours ago, but here we were, about to fuck in my tent.

"Lisa told me you're a stud..."

Kiss.

"Oh yeah?"

Kiss.

"Mhmm. Said you get around."

Kiss.

"I do alright..."

She pulled my shirt over my head and I took her sports bra off, exposing her perky, petite tits, and began massaging them immediately.

"Mmm...you like these tits?"

Kiss.

"I love 'em."

Kiss.

She leaned forward so I could suck on them, and began stroking my cock.

"Ooh," she shuddered, as I went to town on her nipples, sucking forcefully and biting them gently every so often.

She hopped off of me momentarily to wiggle out of her leggings, and I pulled my shorts off before she climbed back on top of me and continued stroking.

We continued the cycle: kissing, dirty talking, sucking her tits, kissing, dirty talking, sucking her tits, all while she slowly stroked my cock, until eventually, the feeling of her hand was replaced by a much warmer, much more familiar feeling.

"Oof," I grunted softly, as she slowly lowered herself onto my cock.

Her pussy was tight and noticeably textured, and given that the temperature had dipped a little, she felt extra warm. Needless to say, being inside her felt good.

"Heh, never gets old right?," she giggled.

"Ugh, never."

It was true. While I had been inside a lot of pussy at that point, the initial thrust felt just as amazing as it did when I lost my virginity. And it continues to feel that way every time I have sex. It's a novelty that'll never wear off. There's something magical about that first thrust.

She started grinding on my cock, and I reached around to rub her asshole.

She leaned forward and bit my lower lip.

"Mmm...you're a dirty one aren't you..."

"Fuck yeah."

She sucked my finger and pushed it into her asshole.

"So am I..."

With a finger in her ass and my other hand rubbing her clit, her grinding started picking up speed, but the material of the tent made it noisy. She only rode fast for about half a minute before we both giggled and realized we had to be a little quieter if we didn't wanna wake anyone, so she switched it up and got on her feet and started bouncing instead. Our fingers interlocked and I helped her balance as she hopped up and down on my cock.

"Ooh, this feels better anyway," she whispered.

She wasn't lying. I always found it interesting how different positions felt better with different women. It was one of the things I enjoyed most about exploring a new partner - finding which position worked best for us.

Sometimes grinding felt better, sometimes bouncing did. Having Michelle's pussy wrapped snugly around my cock while she slid up and down on it happened to feel better than the grinding.

"Phew...wearing me out," she whispered, as her bouncing began to slow down and get more methodical.

"I got you," I replied, and pulled her down so she could rest on top of me, then I spread her ass, and slowly started thrusting upwards into her to give her a break.

"Ooh, now we're talking."

I would slide into her slowly, hold it there for a second, slowly pull all the way out, and wait a few seconds before slowly sliding all the way in again, teasing us both, and making every thrust feel like that first one all over again.

"Mmm...I think I'm in love, haha," she sighed and giggled softly in my ear.

"In love with this dick," I muttered, as I continued sliding in and out of her slowly, trying to keep things quiet.

She rested her chin on my shoulder and whispered in my ear.

"I wouldn't be the first..."

I know it was a mindless, innocuous little throwaway line said in the heat of the moment, as most dirty talk is, but being the cerebral, obsessive over thinker that I am, it did something to me.

The rolodex in my brain immediately started recalling all the previous women who had said something about my dick, and/or had a very powerful orgasm during penetration.

I always wanted to please my partner, and did whatever it took to bring them to orgasm, but there was a difference between making a woman cum with my hands and mouth or even a toy, and making a woman cum with my dick. I know a lot of women struggle to cum from PIV, so I'm always flattered and always feel like a total stud whenever all a woman has to do is sit on my dick to reach orgasm. It gives me confidence in ways nothing else does.

It also triggers my inner caveman, and puts me in dom mode. Michelle was enjoying my cock even though I had barely done anything with it. I needed to give her a proper fucking, to show her how much better my dick could get.

I lifted the cougar spinner off of me and laid her down, spread her legs, and got ready to dig her out.

It was dark in the tent and my other senses were heightened as a result. Rather than fumble around with my hand trying to find her entrance, I laid on top of her and let nature do its thing. My cock found her wet slit instinctively, and I slid right back inside her with ease. The strong smell of her sweaty pussy had completely filled the tent at this point, and only served to make me feel even more primal in that moment.

"Oh my god, this fucking pussy," I blurted out, loud enough for anyone around us to hear.

I couldn't help myself. I thought back to my virgin days when I would hear people talk about how PIV felt "like home," and I remember getting frustrated because it wasn't specific or descriptive enough to capture the physical sensation of sex. And then I actually had sex, and I finally understood what they meant.

Being inside pussy, when it comes to missionary in particular, just feels like home. I know a lot of people think it's boring, and honestly, it's not my favorite position, but physically, it just feels the most welcoming.

"Shhh, haha," she giggled, reminding me of where we were. In that moment though, I didn't care. I wanted to pound that pussy good, and I didn't care who heard it. In that moment, a small part of me wanted to get caught, so anyone who walked in on us would see what it's like to fuck a woman right.

I got to work quickly, taking it all in with every thrust. The smell and feel of her pussy, the moon and stars just outside the tent that I could see clearly since Michelle had left the entrance of the tent open, the excitement in knowing that any member of our group could walk in on us at any time, especially given the way I was fucking.

"Fuck, fuck, okay, shhh...shit...fuck," Michelle moaned, trying to juggle two opposing goals at once - stay quiet, and fully enjoy herself. The former was becoming increasingly harder to achieve with each thrust, but each thrust brought her closer to the latter.

I was getting in there good, digging so deep I thought I'd fuck right through her and put a hole in the tent. Apparently it wasn't deep enough though, as halfway through my digging, she reached into her flexible yogi bag of tricks, and put her legs behind her head, turning herself into a pretzel.

"Oh my god," I grunted, as my cock reached a level of depth inside her I didn't know existed.

I guess she could tell I was getting close, because she started giving me the okay to dump inside of her.

"Give me that fucking cum. Give it to me."

She hadn't had an orgasm yet, and I wanted her to finish before I did, but I couldn't hold on much longer.

"This pussy is so fucking good," I moaned, almost trying to explain and apologize for my soon to be limp cock.

"So is that fucking dick," she replied. I guess we were both close.

I continued hammering away, loud clapping sounds be damned, trying my best to get her there, digging into that sweaty pussy and grunting like a caveman, but I couldn't hold on any longer. I shot my cum deep inside of her, one thick spurt after another as she moaned softly. The head of my cock throbbing and swollen.

Before I could catch my breath and prepare for a potential round two, I heard rustling from one of the other tents. Someone had woken up and it sounded like they were on their way out.

Without thinking, I shot up, taking Michelle with me, my semi hard cock and warm cum still inside of her, and jetted out of the tent with her legs wrapped around me, and hid behind a nearby tree.

It was Lisa.

She groggily walked out of her tent, went to check on mine, saw it was empty, and looked around in confusion.

"Brian?" she called out softly, but loud enough that I could hear her.

"Yeah?," I replied from behind the tree, my cock still very much inside her friend, who was now bent over in front of me in standing doggy position, rubbing her clit vigorously to get herself off.

"Where are you?"

"I'm using the bathroom."

I could feel Michelle's pussy pulsating and she started grinding back against me. She was quietly riding her O.

"Oh okay, sorry," Lisa replied, and walked back into her tent.

I stood completely still and let Michelle finish cumming on my cock, her contractions giving it a nice tug.

"Squeeze that fucking cock," I commanded, as I nibbled on her ear, neck, and shoulders, and reached around to help rub her clit.

She finished her orgasm and turned around to kiss me, jumping into my arms as she did it.

"Wow," she whispered, breathlessly. "Holy shit."

With her legs still wrapped around me, I carried her naked spinner ass back to my tent and the smell of our sweaty, dirty sex was very much still lingering in there.

"She definitely smelled that," Michelle joked.

We put our clothes back on and shared another quick make out session before she playfully grabbed my crotch and said "I'm gonna need some more of that soon," with a devilish grin as she left my tent.

She'd get her wish. Her and I ended up fucking every single day that summer. Every. Single. Day. To Lisa's amusement.

"Michelle says you can fuck," she playful texted me a few days after our trip.

"Ha! And what did you say?"

"I told her, yeah, you're not the first person to say that, haha."

And thanks to Lisa, she wouldn't be the last.

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