This story is about Alessandra, the 20th woman I slept with.

After my experience with Kathy, I reached a level of inner confidence I never had before.

Anytime I doubted myself, I'd think back to her, a woman more than double my age, on all fours, moaning and cursing as I pounded her from behind. If I could make an experienced older woman react like that, I knew I could handle anything regarding sex and dating.

As a result, I went a little wild that summer, starting off June with Kathy, my 10th partner, and ending August with Alessandra, my 20th - doubling my lifetime count in just three months.

I met Alessandra in Vegas. My friend and I had taken a weekend trip there at the end of summer, and happened to run into a bachelorette party at the bar of our hotel.

She was 5'4 and chubby, with tan skin, and long, wavy, almost curly dark brown hair. What drew me to her initially were her big brown eyes and thick eyebrows and eyelashes. I know asses, tits, and legs get a lot of attention, but men really do find eyes attractive as well.

Every so often I'd catch her staring at me from across the bar, only to have her look away once I spotted her. It didn't take long for me to start brainstorming ways to approach her.

The nerdy, shy, inexperienced version of me would've been the one to look away once she caught me checking her out.

The slightly more experienced version of me would've acknowledged she was checking me out, but would've been too scared to approach her in front of her friends, and would've gone home with regret after not having made a move.

But this was the new and improved me. The guy who was getting laid on a regular basis with several fuck buddies, all of whom very much enjoyed the sex. Striking up a conversation with a woman at a bachelorette party was nothing.

My friend and I approached the table and made some small talk. I found out she was Brazilian and had only been in the country a few years. She had an accent, which I of course found super sexy. She was also older than me by a good few years, which obviously wasn't an issue for me, as I had recently been with someone over 20 years older than me (thanks again, Kathy!).

Since I had a pretty good feeling she was into me, I was relaxed and felt confident that as long as I didn't fuck it up, I could make something happen. Despite her being in Vegas for a bachelorette party, she didn't really strike me as the party type, at least not compared to her friends. She was definitely more reserved and introverted compared to everyone else, and as an introvert myself, I could relate, and we started vibing off that alone.

We ended up discussing movies, and I happened to mention one that neither of us had seen, but was on demand back at the hotel, and that pretty much sealed the deal. I asked her if she wanted to come over and watch it, and she knew what I was getting at. She smirked and said while she couldn't leave her friends that night, they were going to spend the next afternoon at the pool, and she would be free to watch it then. We exchanged numbers and I went back to my room knowing the next day would be a fun one.

It was late afternoon, and Alessandra showed up to my room with big sunglasses that hid most of her face, a white top without a bra that barely held her tits in, and a pair of white jeans so tight they looked painted on.

We made a little small talk before I put the movie on, and I gave her some space by letting her sit on the bed by herself while I sat in the chair by the window.

10 minutes into the movie, she excused herself to go to the bathroom, and I don't know - call it a hunch, or just prior experience - but I had a feeling she was giving herself a final check before getting down to business. Sure as shit, once she left the bathroom, she walked over to the chair I was sitting in and rubbed my thighs with a grin. The boldest move she had made yet.

I had her sit in my lap while we made out softly. I loved feeling the weight of her chubby body on me and couldn't wait to explore it.

Her kissing was slow and deliberate, loud and wet. She had beautiful full lips and knew how to use them.

When I think of Vegas hookups, I think of sweaty, dirty, rough, sex at night after coming back from a bar - like I had anticipated when we first met - but this was in the middle of the day, tender, slow, and dare I say - a little romantic?

I pulled her top down and out came her fat, heavy tits, with dark areolas and nipples that were thick and firm. I took one of her tits into my mouth and began sucking while she ran her fingers through my hair and moaned softly.

I guess she could feel my cock growing underneath her, because shortly after sucking on those glorious tits for a few minutes, she hopped off of me and knelt in front of the chair, wiggling my shorts and boxer briefs off.

She held my cock in her hands delicately and studied it intently. Her big curious eyes widening.

"Wow," she said, in her thick accent. "Very nice."

"Haha, thanks," I replied, my face probably beet red from blushing.

My cock was average in length, but I had been told before that I had a nice sized girth. And one woman prior to her had jokingly referred to the head of my cock as "a bulbous beauty," which obviously made me more confident, and I was happy Alessandra liked my cock enough to also say something about it. Compliments like that stay with you forever.

She stroked it slowly, never taking her eyes off of it.

She would give the shaft a gentle squeeze with one hand, and delicately pinch the head with the other.

I was never a fan of handjobs (I could always give myself a better one), but it was fucking hot to see how enamored with it she was.

"This is...so nice," she continued, not knowing how else to compliment a cock.

She grabbed it by the base and rubbed it against her cheeks, closing her eyes and taking it all in.

"Mmm."

"You like that dick?"

"Mhmmm. I never had one like this."

She grabbed her heavy tits and buried my cock in between them, then spit on the head to lube it up and began tit fucking me.

"Ugh. Love those fucking tits," I groaned, as she worked my cock with them.

"Ha...and my tits love your dick..."

She looked up at me with those big beautiful eyes again, and I had to pull her up to make out some more. Like it was a magnet, she never let go of my cock the entire time we kissed. She stroked it softly as we made out, before kneeling back down to work on it some more.

She grabbed it by the base, firmly this time, stuck her tongue out, and slapped my cock against her tongue repeatedly.

"Ah...ah...ah," she said with every smack, before stopping for a second to giggle.

"I'm sorry. I like it too much."

"Haha, that's fine. Do whatever you want with it."

And with that green light, she finally stopped teasing and took me into her mouth slowly. Her eyes slammed shut as she savored it and focused.

"Mmmph," she moaned, as she slowly and methodically began sucking the head of my cock.

She sucked on it firmly, her eyes still very much closed as she was living in the moment.

My hands gripped the chair, and I let out a deep sigh, looking out the window at the crowd below to keep myself from blowing my load too early.

Some people were relaxing by the pool. Some were sharing laughs and having drinks by the bar. All of them seemingly happy and content. But none of them had a beautiful, thick woman worshipping their cock. Sucking it like they'd never suck it again, and wanting to make sure they'd remember the taste of it forever.

If only I had a slot machine in front of me - because at that moment, I was the luckiest man in Vegas.

Part 2 coming later today