Journey to 100 Women: Brian’s Sexcapades (Part 13 – Kathy) [M23/F48] [Cougar] [Squirting] [Dom/sub/switch]

I put her in doggy, ready to fuck her in my previously mentioned, critically acclaimed rhythm, but the reality of the moment struck me.

This woman wanted to get *fucked.*

As seemingly dominant as she was, as hard as she rode me, it was *my* fucking that got her to squirt. It was *my* hard spankings that got her going. She wanted her fantasy of a young, strong, energetic stud to become a reality. I couldn’t be my usual, playful, casual self. I had to be aggressive. I had to match her energy. I was gonna fuck her like a real man.

“This is some good fucking pussy,” I said, finally getting vocal as I slid back inside her.

“Oh yeah? You like that pussy?”

“I fucking *love* this pussy. It’s *my* pussy.”

“Oh is it? Show me.”

Challenge accepted. I could feel a new, primal, dominant energy coursing through my body. Forget about the age gap, the height gap, the experience gap, the fact that she had bossed me around for most of the night, or even the fact that she was upper class and I was a broke little coffee boy. All that mattered was that I was a *man.* *I* was the one with the dick. *She* was the one on all fours, submitting to *me*, like she was supposed to. Her pussy belonged to my cock, and I was gonna prove it.

Journey to 100 Women: Brian’s Sexcapades (Part 9 – Kathy) [M23/F48] [Cougar] [Squirting] [Dom/sub/switch]

At this time in my life, I was a burista at a small coffee shop by my house (college grad working at a coffee shop, surprise surprise).

I became really good friends with Lisa, one of the managers there. She was 37 and married, and also my *boss*, so it was strictly platonic, but we had a lot in common (movies, music), so through that, we became close friends outside of work.

She was one of my closest female friends, and I had no problem talking openly with her about my sex/dating life. She gave me advice when and where I needed it, and over time, became a great wing woman for me. In total, she helped me fuck 5 different women throughout the course of our friendship, simply by introducing me to them, and putting in a good word for me. It’s why I can’t for the life of me understand men who scoff at just being friends with women. But I guess that’s another story.

Anyway, the first of these women, was Kathy.

One night, I got a text from Lisa out of the blue.

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Journey to 100 Women: Brian’s Sexcapades (Part 8 – Kathy) [M23/F48] [Cougar] [Squirting] [Dom/sub/switch]

(A lot of backstory to this one so apologies in advance)

Kathy was the 10th woman I slept with, and the sole reason I even started this journal in the first place. It was such a wildly unbelievable experience, it completely changed what I thought was possible for someone like me, and it was the first time I realized that my journey was gonna be far from typical, which is why I needed to start documenting it.

I suppose I have to backtrack a little, since I’m skipping over some past experiences.

After Lauren (who was my 4th hookup), I fucked another 5 women over 6 months. 2 of them were one time things, 2 were fuck buddies, and 1 wanted something more with me. I didn’t want to waste her time, or lead her on, and told her straight up that I wasn’t interested in a serious relationship with *anyone* at that time.

It was unfortunate, because I really liked her, (and really liked fucking her, obviously), and it was the first time *I* had to reject someone.

Journey to 100 Women: Brian’s Sexcapades (Part 7 – Lauren) [M22/F23]

Her blowjob skills improved, my pussy eating skills improved (it actually became my favorite sex act – eating pussy is comically good), her riding skills became ridiculous, my stamina got better. We were becoming better lovers for our future partners, and spoke openly about everything.

“Right there,” she’d say, pointing to a particular moment in one of our videos where I was fucking her in missionary. I had laid flat on top of her, stomach to stomach, not moving anything but my hips. It was a technique it took me a while to get comfortable with, but one that she loved.

“Look at you go! Look at that hip iso action haha. You’re like a little belly dancer.”

“And you’re a snake charmer.”

“Hahaha. No, but really. More of that, please.”

My stroke game got better. I had learned to hold my nut longer in doggystyle, which was a big thing for me, as I had a pretty strong ass fetish, so the longer I stayed in that position, the better. But also, it was a surefire orgasm for Lauren every single time, as long as I maintained a certain rhythm and didn’t blow my load too early.

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Journey to 100 Women: Brian’s Sexcapades (Part 6 – Lauren) [M22/F23]

I think it’s called “getting lucky,” for a reason. There was *certainly* an element of luck involved in my previous 3 hookups, all of which came from dating apps. They could’ve just as easily swiped on someone else, or bailed on the actual date. It wouldn’t be the first time.

Honestly, you could argue that had I not mentioned that obscure fucking indie show to Sara, we wouldn’t have fucked that night, and I would’ve still been a virgin. Every action or inaction leads to something else.

I could’ve just as easily not kept in touch with Lauren after college. She could’ve just as easily not found out about her boyfriend’s cheating, or just not have posted it to social media. I could’ve just as easily not seen the post, or just as easily not have reached out. But here we were.

As I mentioned earlier, *someone* had to fuck her. It was “someone else” for the majority of my life. Well, I was gonna toss my hat in the ring every chance I got going forward, which is why I was the one about to get laid.

Journey to 100 Women: Brian’s Sexcapades (Part 5 – Lauren) [M22/F23]

Thanks everyone for the follows and kind words on my previous story. I’m definitely gonna keep them coming.

This next one is about Lauren, the 4th woman I slept with.

Initially I was gonna limit the stories to just the *really* wild ones, but I realized even the more tamer ones have their purpose, especially when it comes to the big picture regarding my journey.

Again, every experience has taught me something, and every woman has brought something different into my life that’s made me who I am today. Yes, my stories will mostly focus on the physical aspect of sex, but I also want the actual women themselves to get their recognition as well. I wouldn’t be here without them. I’ve been in my fair share of pussy, but every single one of them was attached to an individual. And no matter how high my partner count gets, I won’t lose sight of that. So while this is a celebration, in large part, of the female body (some specific body parts will be celebrated more often than others lol), it’s also a celebration of women in general.

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Journey to 100 Women: Brian’s Sexcapades (Part 4) [M22/F26] [Virginity]

My overarching thought in that moment, aside from the relief of no longer being a virgin, was this feeling of being home. Being inside a pussy for the first time was both a completely new experience and a completely familiar one. It felt like I had done it a million times before. It just felt…natural. Once again, that primal fucking instinct.

She grabbed the back of the couch, balanced herself on her feet, and began bouncing slowly on my cock. I reached underneath her, grabbing onto that soft juicy ass again, to help her keep her balance.

I could still smell her and taste her on me, I could hear her wetness as she bounced, I could feel myself in her, wrapped up in her warmth. I was experiencing every pussy-related sensation at once. It was pussy overload.

After the bouncing, she balanced herself on her knees, and started grinding back and forth, which was a new sensation, but equally as awesome.

I directed my attention back to her fat fucking tits, squeezing them as she rode my cock.

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Journey to 100 Women: Brian’s Sexcapades (Part 3) [M22/F26] [Virginity]

I got between her legs, and was now eye level with her pussy. I repeat – *I was eye level with her pussy.* The formerly kissless virgin who currently had a woman’s salvia all over his cock was about to return the favor to that same woman.

The first thing that hit me about her pussy was the smell. I will say, of all the things I love about pussy, smell is my favorite.

I obviously didn’t realize it then, but over time, I loved how different women can smell, and how different the *same* woman can smell, depending on a variety of factors. It’s her signature scent. It’s what makes her, her.

Sara’s pussy had a strong musk to it, and it smelled almost identical to an armpit. I loved it then, I love it now. And just like that, one of my many pussy-related questions had been answered. I didn’t know what *every* pussy smelled like, but I knew what Sara’s smelled like. Now, I was about to discover her taste.

Journey to 100 Women: Brian’s Sexcapades (Intro)

My name is Brian, and to say I’ve lived two different lives is putting it mildly.

For the first 21 years of my life, I was a stereotypical nerdy, kissless virgin. Scrawny, shy, and zero “game” to speak of. Women might as well have been another species to me. That’s how far removed I was from interacting with them or understanding them.

When I graduated college without having so much as held a woman’s *hand,* after being told that college was “the easiest place to get laid,” I felt like a complete loser, and decided I had to make a serious change in my life, or this was gonna be my story forever.

No more staying at home, doing nothing, wasting my life. No more jerking off to porn and wondering what pussy felt like, smelled like, or tasted like. Fantasizing about what it would be like to get a blowjob, or even just to *kiss* a woman! I was gonna work on myself and find out what all those things were like, once and for all.