Chrissy and I had agreed to meet at a brewery on the east side for our first date. From her profile and our conversations on the dating app, I knew Chrissy was 27 yo, 5’11” and had been a D1 basketball player in college. For the last four years, she had been a working professional for a big sports company.

The best way to describe Chrissy physically was “cute face with a hot body”. She had as pretty a smile as I’d ever seen, and bright blue eyes. Her hair was straight, brown and about armpit length. From her photos, she still looked fit with a nice flat stomach, and perky round boobs. A 32C if you forced me to guess. Moreover, whether she wore jeans or a bikini, she couldn’t hide her big curvy ass (probably a 36) that stood just above her long shapely legs. I had already jerked off multiple times to a photo of hers on the app where she was posing on her knees in a bikini at the beach. I wondered how many others had done the same.

I got to the brewery five minutes early and grabbed an outside bench table for us in the corner. On this hot Sunday afternoon I was wearing jeans with a tight black T-shirt to subtly show off my fit body. I’m 29, 6’3″ and regularly workout and play soccer to keep myself in shape.

About 10 minutes after I got there, I saw Chrissy walking towards my table. She was wearing a white sleeveless button down blouse and tight black shorts that ended at her mid thighs. Her long legs had no other coverage downwards for miles until you reached her feet where she was wearing low-top sneakers. She was turning a head or two in her direction due to her legs out on display, and her shapely round ass pressing hard against her tight shorts. I knew she was cute from her photos. In real life though, she was STUNNING! “Hiiii”, she smiled as she extended her arms out for a hug. I pulled her in for a big hug and could feel her boobs pressing against my chest. Her body smelled of Jasmine. “You look stunning”, I said. “Thanks, you’re not bad yourself”, she giggled and blushed. As she sat down opposite to me, I noticed I could see the outline of a black bra through her thin white top. What wouldn’t I give to get my hands underneath….

We ordered a couple beers and our conversation was easy, organic, and fun. Two rounds in, and we were getting pretty flirty. She was playfully punching my arm whenever I made fun of her. And I would find excuses to touch her arms and forearms. I caught her staring at my arms and chest on multiple occasions, and I sure was guilty of staring at her breasts numerous times. I didn’t know if it was deliberate or she just needed a stretch, but at one point she raised her arms overhead and stretched her torso out for a good 5 seconds, sighing deeply. Her sleeveless top rode up to her upper belly, exposing her flat stomach and belly button. I saw she had perfectly shaved, white, silky smooth armpits. As her breasts pushed to the front of her top from her stretch, they showcased her voluptous torso beautifully. I was already aware that she was well endowed in the curve department, but internally felt like a kid in a candy store admiring her torso.

As we continued to talk, she mentioned she liked sports, hiking, coffee, wine, and light beers. She still hooped, not fazed at being the only girl in her neighborhood’s pickup basketball games. While she lacked some strength and speed to the boys, she played hard with sheer determination, unafraid to play physical and dirty if she needed to. I learnt that she was very competitive about nearly everything, and came up with a plan to use that to my advantage.

“Bet I can chug my glass of beer faster than you”, I casually teased, after I returned with our third rounds from the bar.

“Oh you’re on. Prepare to lose, mister”. Exactly what I wanted.

“What do I get when I win this bet, Chrissy?”.

“It doesn’t matter, coz you won’t. But when I win, I want you to pick up the entire tab for the evening”. She gave me a competitive smile that I found cute rather than threatening.

“Oh Chrissy, I would have offered to do that anyway. But fine, you got it. And we still haven’t decided what happens when YOU lose”.

“Aargh… fine. I’ve seen you staring at my boobs since I got here. So if you win, which you won’t, I will unbutton my top 3 buttons so you can have an easier look at my cleavage”.

I couldn’t believe she was so proud and confident to make this bet.

“What? I don’t think I’ve been ogling that much? I mean… you’re sexy!”. She blushed and giggled as I said that.

“I was kidding about you ogling. Ok only half kidding actually. I’ve seen you look in that direction a few times. Honestly, I find it quite flattering …. since I clearly find you attractive as well”. She was smiling and blushing even more now.

After a pause of few seconds, she said “So what do you think about the conditions?”

“Deal, you’re on!”, I replied.

We counted down and began chugging our beers and while Chrissy was an above average beer drinker, I finished my glass a good 5 seconds before her.

“Grrr… get that stupid grin off your face”.

“I will. As soon as you unbutton your top”.

“Fine”, she pouted and unbuttoned the top 3 buttons down to just below her breasts.

A new world had opened up to me. I could see so much of her cleavage now. Tops of her big, round milky white breasts visible almost down to their centers where a thin, black lace bra was annoyingly in the way.