Date #31: Monica the Bland
Another 'meh' experience that taught me a good lesson and this is where I really tightened up my standards for a while. Of course, I'd be fooled again in short order, but with Monica I knew I was taking a risk.
Nothing about her profile screamed "hot", but she was pretty cute and seemed cool. Her big tits didn't hurt either. She was short, strawberry blonde hair and lots of freckles, which is a major weakness of mine.
Normally I plan my dates the same way - dinner, a spot to jump to nearby for something fun, another place close for a drink, and then maybe somewhere after that for some privacy. I don't always jump through all the hoops. Depending on how it's going, I might just exit after dinner or skip something in the middle, but if things are going well, I always look for that private spot to get cozy.
I took Monica to a place with nothing directly nearby to hop to after dinner. There's a Top Golf not too far away that works for spot #2 if things go well, but not much else going on. Needless to say, we didn't make it past dinner.
When she arrived, my fears came to fruition. She had cleverly taken pics so she was far less cute in person than on her profile. I'm pretty good at identifying this out of pure experience, but she did fool me a bit. Not that she was horrible or anything, but even though she sported wonderful cleavage, I was not into her. She had a boxy body, not fat, just no curves to match her big tits. Really, not my type.
We had a nice dinner, conversation was strained, though we did find out we had a mutual friend. A guy she's known since high school worked for me for a while more than a decade ago. We joked about how he's so high strung and a bit weird, but that only took us so far. She just wasn't a super interesting person. We hugged at the end and parted ways.
Lesson learned, though sure to be repeated, and it did lead me pretty directly to my next girlfriend.
Date #32: Tracey the Sober
Tracey was NOT sober. Tracey LOVED to drink. I love to drink. It wasn't the whirlwind, 'direct to girlfriend' experience like the others before her, it was more of a slow burn. We fit very, very well together, but things fell apart in a hurry.
We messaged for about a week before we could get together. The first date was a lot of fun. I made plans to eat at my favorite breakfast spot that serves mountains of food, but also does dinner as well (breakfast/brunch is way better than their dinner if you're wondering). The next spot was less than a mile up the road, a retired mall converted into an indoor amusement park. I figured it would give us a lot of options and if things went well, we could find a little spot to hide and do a little making out.
I pulled in and waited for her, watching the cars pull in as I always do, texting her that I arrived. She said she was a few minutes out and next thing I know, I see this buxom blonde, making her way to the door. I missed her when she pulled in, but was high as a kite on her watching her walk in from a distance.
Tracey was tall and thick. Perfect curves, a beautiful smile, straight natural blond hair almost to her ass, and bright blue eyes. Hefty double-D's, narrow waist, wide hips, and a big fat ass that jiggled just right. She kept a little tan going year-round, but only "just to have a little color." I knew she was attractive on her profile, but seeing her in person drove me wild. Basic black shorts, tight green top - modest, but incredibly sexy.
I jumped from my truck and walked in.
"BOO!"
I nearly jumped out of my skin. She got me. Standing behind the door watching me walk up, she waited for her moment and jumped out behind me, scaring the shit out of me. And that's how it was with her. We ALWAYS joked and played and teased each other. She challenged me in the best ways. It helped that she was incredibly smart, out-going, and really fun.
Tracey was a doctor at a major hospital chain, the same one where my ex worked. She was one who didn't actually know her, but knew of her. She had stories for days and was more than happy to diagnose everything I had going on, even when I didn't ask. That was part of her charm.
Dinner went swimmingly, but she shot down my plan pretty hard.
"That place sucks. It's boring. We'll walk around for 20 minutes and be done with it. Let's just go to [my standard date place with the big Ferris Wheel]."
No problem, I don't mind an audible.
She made it really easy. Everything just flowed. We stopped in a bar, had a couple of drinks, flirted endlessly, and then made our way to the giant slingshot ride and crazy 400ft spinning swings I hadn't tried yet. What a blast, she was so fun. More drinks at another bar and we made out at her car before parting ways.
Next date was even better. More fun energy. Restaurant, walk in the park around a lake, another bar and we got drunk. Really drunk. Shots and drinks and just so much fun. We ended up missing last call, making out on the couch in the mostly empty bar, looking up and finding ourselves all alone with a bartender who was super cool as he made is closing rounds.
On our way back to the parking garage, we kissed more and she was unrelenting. She said she was too drunk to drive so she ordered an Uber. Except, she didn't. We just kissed and fondled on the sidewalk for almost another hour before I asked her to check on her Uber.
"I guess I forgot to order it."
Making sure she did this time, we continued to play with each other until it pulled into the adjacent convenient store. 330am and I was on my way home.
The next morning, I woke up to a series of texts. Apparently, she forgot her house keys in her car, couldn't get into her house, she ordered another Uber, but her phone died, causing a major delay in the driver finding her. She got back to her car eventually and drove home, pulling in her driveway just after 630am. What a shitshow.
The red flag of it all was, she didn't remember a lot of our date. She didn't remember going to that bar or nearly anything that happened after that. Her brain turned back on somewhere during her initial Uber back to her house, leaving a ~5-hour gap. Whatever, we did drink a lot that night and she seemed like my ideal woman. I felt myself getting that girlfriend vibe again.
Third date was another awesome one. We went to a little amusement park, raced go karts, made out on the Ferris wheel, kissed and held hands waiting for someone to open a ride for us, and snuck some flirty kisses everywhere in between. While I had done a bit of roaming with my hands, nothing more had happened to that point and I was dying to get my hands on that sexy thiccums.
I went straight for the kill at that point. I didn't bother to set up another date, I just invited her over. She showed up looking like a full meal in rainbow leggings and a tight sleeveless t-shirt, cut off just above the waist, her curves on full display.
She mentioned playing a game before she arrived so I readied some good ones from the game rack. We were both hungry, so I ordered delivery and lit all my candles just before she got there. My game selections were not intriguing for her, so we ended up laying a Rummy, eating, joking, teasing, drinking, and laughing for almost an hour.
After my dominating card performance, I cut the chase and pulled her into the bedroom. In a tornado of tongues and hands and clothes flying all over the place, I drowned myself in her freshly shaved little pussy. Licking, slurping, driving my middle finger around her G-spot and tonguing hard on her cute little clit. Her pussy was absolutely beautiful - Georgia O'Keeffe wouldn't have bothered even picking up a brush if she saw this thing.
Not only did it look wonderful, it was wildly tight. Tight like Lisa was that night on the beach. A second finger was totally not in the cards at all. I knew she was a little nervous, so when I climbed on top of her, my ravenous nature eased. She loved the way she tasted on my lips, licking around them and whispering about "my flavor."
It was quite hot and my rock-hard shaft ground up and down her sopping hilt, the head nearly poking in a few times.
"I'm on birth control, but no."
"No worries."
I climbed over to the side and pulled a rubber from the nightstand.
"Good boy."
"Always."
Kneeling above her, I ripped the plastic foil open and rolled my custom fit condom (seriously, buy them) over my straining cock. She held her legs back and caressed the back of her thighs, staring into my eyes as I pressed in the tip.
"Oh!"
Her hands pressed against my stomach to stop my entry beyond the first inch.
"It's a lot!"
"Shhh... I'll go slow."
Slow is an understatement. Every millimeter into her impossibly miniscule hole was met with a push back against me and a deep breath, then she eased back and invited a bit more. It's not an exaggeration that it took more than a minute to get beyond the halfway point. Back out a little, then in just a tiny bit deeper. A solid 5 minutes kissing her as she held me in a bear hug and dug her heels into my ass until I finally reached the bottom.
Slow and steady as to not hurt her, never again pushing all the way to my base. She moaned and writhed, holding me tight. It was pretty uncomfortable to be honest, but after nearly a half hour, I spilled into the cover and we laid together.
"You're really tight. Are you nervous with me?"
"It's just new. And well, my last boyfriend was pretty small."
"Seems like it's been a while too."
"Almost a year."
"Ok, just relax, you're safe here."
"I know, you do make me feel safe."
We cuddled a while and junior started to stir again. Similar to before, I made her cum with my mouth, then very slowly fucked her. The second time was definitely better than the first, but she still had that vice grip. After round 2, we kissed and cuddled, talked a bit, and fell asleep.
The next morning, she got up and left as I started getting ready for work. I still had all the girlfriend vibes despite the mediocre sex. She was so much fun and smart and we vibed so well, I figured sex would be something we could just work on.
That weekend we made plans to grab food at a trendy taco spot near her house. I packed up my dog, went over and picked her up. She looked super sexy in her black and white striped skin tight maxi-dress (God I love those). We shared a glass of wine as she finished up her hair, I poked around her impressive house. This place was HUGE, valued at nearly a million dollars (thanks Zillow) and sparsely filled with fine art and expensive furniture.
We had some shots and a couple of drinks with our over-rated tacos and headed back to her house. She popped a new bottle of wine and we sat on her patio while she heated her hot tub. We laughed and talked and got mildly frisky, finishing off the bottle and testing the water.
Her heater wasn't working right so we talked skinny dipping, but never made it into the pool. We just started kissing and playing on her patio sectional. Once her dress came off and her big jiggly tan lined ass was in the breeze, I was all over her. My clothes came off and she dropped in front of me, sucking my dick with entirely too much teeth.
