The 50-First Dates Ch. 31-40

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.

"Open wider."

"MMMMMHHMMM."

"Suck harder."

*sluuurp*

"Come up her and fuck me."

I reached for my shorts and pulled out a condom, she ripped it out of my hand, tore it open, put it in her mouth, and rolled it down with her lips. Super hot. She climbed aboard and slowly guided me in. Another very tight experience, but she really got into it. Awkwardly bucking on me, she started to bend me in uncomfortable ways, so I turned her around and laid her on the sofa. Another lengthy missionary session and I dumped into her again.

"I'm going to open another bottle."

She seemed fine and her white wine was pretty low content, so I didn't object. She filled our glasses and we lounged around in the nude, sipping wine, cuddled into the corner of her patio sectional.

"Let's watch some TV."

Cool, it was getting late and seemed like a good time to wind down. Her Firestick wasn't working and I spent a solid 20 minutes trying to figure it out as we finished the bottle. I finally threw in the towel and we climbed into bed.

We snuggled together and with my exposed cock on her broad cool ass, intentions began to grow. Very quickly things escalated and she was facing me, stroking my cock against her.

"Have you been tested?"

"I test regularly. Last time was a little over a month ago."

"Have you been with anyone since?"

"No, just you."

"Fuck me."

I rolled on top of her, my flexing helmet immediately finding her hot, dripping center. I eased myself in as she started to open up a little more to me. Still very tight, but no more stopping and starting or wincing in pain. So slick, so tight.

I couldn't really pound her, but I was excited about the progression and this time was much, much more passionate.

"I want on top."

Ok, my favorite. Throwing her thick thigh over me, she sat down on top of my due north, directing me in to her clamping tightness. I held her big tits together, sucking back and forth between her pale areolas and pink button nips. She slowly rose up and down as I felt her cream spread over my crotch.

Her pace increased and her tightness once again caused me to bend uncomfortably. Just as I was about to switch positions, get behind her, and enjoy her big flowing ass, she rose up a little too far and sat back down very hard, bending my steel rod in half.

"Ouch fuck!"

"What?"

"You just bent me... hard."

"Sorry."

My cock instantly softened.

"It's ok, but it hurts. I can't right now."

"Ok, sorry."

"It's ok, but it's already late anyway, let's just try again in the morning."

"Ok."

Once again cuddling under the sheets, I began to doze off just a few minutes later. She began grinding against me and turned to me for a kiss. We kissed for a few seconds and she began stroking me.

"I'm not ready, it still hurts."

"What?"

"It still hurts and I'm going to need more time to recover."

She looked confused, "what?"

"Let's just go to sleep."

"Ok."

I didn't start drifting again right away. I laid there for about 15 minutes, then once again, she started getting randy. Exactly the same as before, giving me the ass, turning and kissing, then stroking and trying to climb on top.

"Hey, no."

"What?"

"My dick hurts."

"Why?"

"Uh, cause you bent it."

"I did?"

"Yeah, like a half hour ago. I just can't right now."

"Sorry."

"It's ok, let's just get some sleep."

"Ok."

Maybe 10 minutes this time, same as before.

"I'm just going to go."

"Why?"

I got frustrated.

"Because my dick hurts and you just won't stop."

"What's wrong?"

"You bent my dick, it hurts, and you keep trying to fuck me!"

"Oh, I'm sorry."

There was blankness behind her eyes I hadn't noticed before. The lights were on, and I'm sure someone was home, but nobody was coming to the door.

"It's ok, I'm just going to go."

"Ok."

I went outside and gathered my clothes, grabbed up the dog, and went back to her bedroom.

"Ok, I'm leaving."

"Why?"

"I'm going through it again. It's fine. I'll talk to you tomorrow."

She was confused.

"Ok."

I went out to my truck, plugged in my phone, and set my GPS to 'Home.' I threw it in reverse and there she was.

Tracey had stumbled out into her driveway, fully nude.

"What the fuck are you doing?!"

"Where are you going?"

"I'm going home!"

"Why?"

"Go inside."

I threw the truck into gear, jumped out, and directed her inside.

"I don't understand."

I was so frustrated and a little freaked out, but I had no words.

"Goodbye."

I scrambled to my truck and took off. The next morning, I woke to a text.

'What happened to you last night?'

Sigh.

I explained everything and she apologized profusely. As we chatted, some of the pieces fell into place in my head. Tracey drank a lot on our dates. She blacked out regularly. She never got sloppy, but something in her brain just shuts off at a certain point. When I threw away her bottle of wine before we left on our date that night, her recycle bin was full of bottles and nothing else. Tracey was an alcoholic.

Eventually she tired of the texting and called me. I her told her that I needed some time to think about things and really wasn't sure if I was going to pursue it any further. There was such a connection though that I wonder if maybe I was over-reacting.

"If you just want to end things, let me know. I feel like I'm being dumped."

"I don't know what I want right now. Last night was a lot."

"It feels like a break-up."

"It's not, just give me a few days to get my head in order and I'll let you know."

"Ok."

That evening she called again, this time crying.

"I don't date a lot and I really like you. I feel like I fucked it all up."

"I don't know. I like you too, but I think the drinking is a problem."

"I'm not always like that."

I wasn't going to argue, but the writing was on the wall. Her denial of her situation was a major turn off. I did nothing that evening, just sat home and watched movies. Around 9pm I got a text.

'I'm hanging with my friends, you should come!'

I ignored it.

'Come party with us!' an hour later.

Ugh, I put my phone down. A while later I fell asleep.

The next morning, I woke up and picked up my phone.

'Fuck you.' Just after midnight.

I was done.

'I'm guessing you don't remember sending this.'

'Jesus Christ, I'm sooooo sorry.'

'It's ok. I like you. I really like you. But you have a problem with drinking. I'm not one to judge, I love to drink too, but you go too far and it's scary to me. I don't want that sort of responsibility for someone else.'

'I understand. I'm sorry.'

And that was it. It was over. Too bad too because we could have been a crazy power couple. We meshed so damn well and the sex seemed to be working itself out, but I can't handle being with someone who cannot take care of themselves or handle their liquor.

I took another break after that. I did that from time to time either when something I thought was going somewhere didn't or I just got sick of the rat race. A little time to yourself is a great idea when dating as much as I do.

Date #33: Malorie the Chameleon

Malorie is a box of chocolates; you never know what you're going to get. Her profile looked fun, but she looked wildly different in every picture. You could tell she was attractive, but every angle almost looked like a different person. After matching and starting a conversation, I almost didn't set up a date simply because I really wasn't 100% sure what I was getting into. However, she was fun and I was bored, so one day I asked her to meet me for dinner and she accepted.

Waiting in the parking lot as she rolled in 10 minutes late, I caught a glimpse of her in her car as she parked in front of me. Totally cute! When she got out of the car she was also... Totally fat!

Not a bad fat, mind you, but too big for my tastes. I should have known from experience that when you have someone who's pictures aren't quite accurate in that they look very different in each one, they're probably an expert at hiding things. Turns out though, she was actually prettier and her huge ass, thighs, and bowling ball tits weren't totally off-putting.

I knew as we walked to the spot that she was casual only to begin with so maybe we'd have some fun, we'd hook up, and that would be it. If I'm honest, the fact that she was looking for both guys and girls did tip the scales in her favor for meeting up and more.

We ate dinner at a standard outdoor dining spot of mine. She was a ton of fun and I teased her about being a chameleon. She was confused and then I told her to go through her profile, which lead to her going through her social media and me picking apart how every single picture looked almost like a different person. She was game so it was a good time.