The 50-First Dates Ch. 01-10

Forward:

I'm a 39-year-old, successful bachelor. I'm an executive, an investor, and a player. I didn't set out with this goal in mind, but life has a way of sorting people out. This is where I ended up. The following is a trip through my growth from hapless passerby, to expert tactician in the world of online dating and some of my more interesting experiences over the last 20 months.

There were many more than 50 dates. At one time I had a new date, every day, for nearly a month. Even with the several times I focused on one woman or just took a break from it all, it's safe to say I easily broke into triple digits. A few times along the way, I totally fell in love. Not with any of my dates, but rather with courting women. The initial messaging, the exciting first impression, the laughs and flirting over dinner, and the build up to that first kiss, and more.

I'm really fucking good at it. I guess I had some skills to begin with, but they've been sharpened to a scalpels edge through repetition and a few mistakes along the way. I can date beautiful women, 5 at a time, with my eyes closed. I am a dating expert.

Background:

Long story short, life has taught me an important lesson: I cannot be trusted to love. If I fall in love, I completely lose my mind and every bit of sense I had along with it. It's forever with me, and I do not believe that I won't just end up fooled again. I'm so confident in this fact that I don't think I can really allow myself to ever do it again.

Out of pain I devoted my life to my career, hobbies, and interests. I stopped looking for any sort of relationship. I didn't even date for the longest time after my failed "forever" relationship in my early 30's, then I ebbed and flowed through hookups and the occasional short-term relationship. After a while it got tedious. I even stopped hitting on women. I just threw in the towel. I still fell into a one-night stand at the bar every now and again, but my 'love life' was officially dead.

My friends, family, and therapist have all been encouraging me to put myself out there for a long time. About two years ago, their harping began to take root. Maybe I was ready to date with a purpose. Maybe I could trust myself to love again. These thoughts grew and grew over the course of a few months.

Running into a buddy I hadn't seen in years really sealed the deal.

The Beginning:

"Are you on Tinder, bro?"

"No, I don't fuck with that stuff."

"You're missing out man. There's an endless supply of new pussy. It's like I'm at the bar hitting on 20 hot chicks every time I take a dump. It's magic."

"Well, that sounds romantic."

"There's apps for that too, if you want."

"I'm good."

"When's the last time you even had a girlfriend?"

"I dated a girl a while back."

"Months? Years?"

Shit, thinking to myself and running the numbers quick. It had been almost 6 years since I dated anyone seriouslyHeathanyoneanyonasdf. Sitting in that thought, I was sad that I pissed my life away with a handful of bar hookups and never a true, loving relationship. All the voices of, "you owe it to yourself to find someone" and "there's no reward without any risk" echoed in my head and I wondered if I was ready to take that chance again. I got to thinking that maybe I was ready to enter a real relationship again.

With Dave's help, I set up a dating profile that night at the bar.

I did nothing with it. Just sat on it. A few days later I opened it and had a few messages. It was the cantina scene from Star Wars - nobody I found remotely attractive, to say the least. What exactly was Dave doing out there?

I decided to try my hand a swiping one evening. Tons of profiles of women my age, divorced with children, mostly. I didn't want kids. I mean, at one time I was in love and I did, but I was too old to be starting a family anyway. And someone else's kids? No thank you. Where were the women without kids?

I played with the filters and opened up a broader age range, figuring I'd be more likely to find women without children if I looked well beyond women my own age range. 18-44. The low end seemed ridiculous, but what the hell? You never know.

I started swiping more over the next few days and started to get a response. To my surprise, I'm a total catch. There's a lot of women out there looking for a man just like me. Despite the apparent success, I still wasn't finding quite as many women I found attractive, so I bit the bullet and opened up my option to women with children.

As things progressed, I ended up removing all my filters outside of distance and age, and I held those pretty loose. I found out later that on some of the apps, if someone left something blank and you selected that as a preference, it would filter them out. I did my filtering while pooping, like a gentleman.

It all started off innocent enough, thinking maybe a relationship could be achieved. My mind went back and forth as I gained experience, but I just couldn't open up. When I felt I could, things didn't work out. The good news is, I found a rhythm and as Dave said, an endless supply of women looking to date a guy like me. Tons of lonely divorcees needing a good dick down to get over their ex and unfortunately, many who obviously couldn't handle being alone and were monkey-branching from one relationship to another back-to-back-to-back. Really pathetic.

There were some "never married"s, a handful of "just looking for fun"s, but most I found wanted something serious even if they acted otherwise. I was honest with everyone, but still hurt some feelings along the way unfortunately.

I had a few conversations going when Reyna popped up. My first, actual online date.

Date #1: Reyna the Shadow

A spicy little Latina in her early 30's. She was ok in the face, but had a nice thick little body. Short, squat, big ass and thighs, jet black hair and olive skin. She was sexy. We matched and she began messaging right away. Within an hour she asked for my number. Minutes later she called to "make sure I was real."

I appreciated how aggressive she was.

We agreed to meet that night for dinner. Some texting back and forth and it honestly felt really fun to flirt like this. Flirting with intention.

I was a little nervous when I pulled into the parking lot. I sent a text informing her that I arrived and she immediately replied saying she was at the light and was about to turn in.

A minute later, she pulled in and I stepped out of my truck to greet her. She was shorter than I expected, but her pictures on her profile were accurate. Though, I immediately noticed something was off.

I gave her a hug and she seemed very shy and timid. Walking in I asked about her day and she gave me one-word answers; something that would continue the rest of the night.

We sat down and she was visibly shaking. I tried to console her and offered to order a round of drinks to calm her nerves. Red flag number 1: She doesn't drink.

Struggling to maintain anything resembling a conversation over our iced teas and fajitas was pulling teeth. She couldn't even look at me. I lost some patience and questioned her directly, asking how she was so aggressive up front, but now so meek in person.

"The way you look at me.... It just makes me feel naked."

What. The. Fuck. Red flag #2.

It didn't get better from there, but she started to open up a little and admitted, she had three kids. That tidbit wasn't on her profile, but hey, she was talking at least. In talking about them, she asked if I wanted to see a picture. I didn't, but I was nice.

Next thing you know, she's walking me through dozens of pictures of her kids growing up over the years and then the kicker.

"They don't need a stepdad, but it would be nice."

Red flag #3, the alarms were blaring!

Just when I thought it couldn't be worse, she started telling me about her job. The more she talked, the more familiar some of what she was saying started ringing bells. Then she hit me with the name of her boss.

Boom. My ex.

I'd love to act all big and bad like I didn't give a fuck, but she completely fucked me over. I mean, it's all good now, but listening to this girl talk about her really rekindled the hurt I felt all those years ago when I found out she cheated on me and the subsequent months (years) where she went out of her way to hurt and manipulate me.

Good thing I was able to get over that sting pretty quickly, because it just so happens that my ex apparently works with a lot of single women and she'd come up over and over again in my dating life. Now it's just a funny thing that comes up and truth is, my story is shared by so many women that it really helps me bond with my dates.

Note to the fellas - be honest, even when it's ugly and some of the details don't paint you in a good light. There are so many bullshit artists out there that women are very appreciative of a man who isn't afraid to tell the truth. And I do, always. Even when there's things that become dealbreakers, at least I know I won't have to live a life with of anxiety wondering if my significant other will find out the gory details of my past and it hurting them, or causing them to leave me.

Regardless, working with my ex is red flag #4 - CHECK PLEASE!

We finished our meal and I picked up the tab, then walked her to her car. I gave her a hug and turned to walk away.

"Hey. Do you want to sit in the back of your truck and talk?"

I was confused.

"The back of my truck? Like the backseat?"

Visions of peeling back her skin tight black pants and playing with those perky little tits that swung free under her white silk blouse had me wondering.

"No, put the tailgate down and we can talk."

Against my better judgment, I obliged. I learned not to do such things pretty quickly after that. If I'm not feeling it, no sense in prolonging the inevitable. Go straight for sex or just cut her loose. No in-between. It won't get better.

Sitting there with our feet dangling and watching four lanes of traffic whiz by, she actually started talking to me normally. Telling me some stories about growing up, more about work, and her travel plans. Blah blah blah.

I just nodded along and 10 minutes later I was faking yawns and talking about going home. Walked to her car, another hug, and we were off.

Except, we weren't. I sat there in my truck. She sat there in her car. Headlights shining across to each other. Almost 5 minutes later, I get a thought, "Maybe she's worried that I'd follow her or something."

Shit, there I was trying to be a gentleman, waiting for her to leave, making sure she got off safe as it was dark and nobody was around. Fuck, ok Jack, time to go.

I pulled out of the space and paused to let a car go by before heading out of the lot. She followed. My instincts were correct! She was waiting for me to leave. Good going.

I turned and went to the light. She followed. Wait, she's supposed to turn the other way. Hmm. I guess there's a couple gas stations this way, none the other way that I know of. Ok she needs gas.

The light changes, I turn, she turns. I drive past one gas station, then another. "FUCK, THIS CRAZY BITCH IS FOLLOWING ME!"

I jammed the pedal to the floor, barreling through the next light as it changed to red and she was still right there. I completely ran the next light, turning right immediately after, whipping around behind a shopping plaza, screeching tires back onto the road, and doubling back in the wrong direction. I had lost her.

What the fuck!

I get home, replied to some messages on the app, put my phone down and closed my eyes. Just as I was dozing off, the phone buzzes.

Reyna.

Open the screen and it's a series of lingerie pics. Bright green lacey body suit, high cut thong, and perfectly perky little tits pointing right at me. She was bashful enough to cover her pussy, but each picture was more suggestive than the last. The final picture was her bent over, squeezing her juicy ass and biting her finger. If she wasn't so crazy, I would have loved to fuck her. Her body was sexy as all get out, with just the right amount of chub like I like in all the right places.

I ignored it. I figured I could just walk away unscathed.

The next morning as I was getting off my exit for work, another message.

'I had a great time last night. Hope you liked my pictures.'

As I parked, my head spinning. How do I handle this?

Wrong. Wrong is how I handled it.

I replied back that I had a nice time, didn't feel a connection, and like a dumbass said, '... but those pictures were in appropriate.'

My phone buzzed constantly for the next half hour. Walls of text. 'I can't believe it, I thought we had a connection...' 'There's nothing in those pictures you couldn't see any time you went to the beach...' 'Are you gay or something?'

After figuring out how to block someone on my phone, I deleted everything and unmatched on the app. Fucking crazy, but I liked to think I learned something.

Date #2: Brynn the Kisser

Brynn was actually my first match. She looked like she had a killer athletic body, despite being in her early 40's and not an avid gym goer. Not that it's not possible of course, but one thing I found on the app is finding a woman over 40 with a lean, athletic body were pretty rare outside of total gym rats. I don't do gym rats and like a thicker woman, so it's not a problem, but it's an apt observation.

I actually wasn't that attracted to her face, but her impressive natural physique and being super fun and nice through messages, had me intrigued. She was 5'7", kinky curly hair to her shoulders, freckled pale skin, and an adventurous personality. Just a few days off my disastrous first online date, I was with her - my 2^nd online date ever.

It just so happened to fall on the 4^th of July. I made reservations at a nice spot near the beach, within eyesight of a big fireworks display. I figured we could eat on the patio, watch the fireworks, and if things worked out, maybe head to the beach where there would be fireworks of our own.

The spot wasn't convenient for either of us, so she met me at my house and we drove together. The very first thing I noticed when I met her at her car was, she looked way older than her pictures. Her body was totally on point, but the face was a little leathered. A woman who grew up in the sunshine state and discovered sun screen 3 minutes ago. She wasn't unattractive, but I wanted someone with a more youthful appearance. I will say, the little bit of panty flash she gave me getting out of her car to greet me was a nice touch.

We had a few laughs on the drive and while waiting for a table to open up, talked over beers at the bar next door. The more I drank, the prettier she got. By the time we ate, we were both a little tipsy and basically missed the fireworks. She had nice blue eyes and was fun. Her freckled cleavage and pale skin gave me ideas.

I paid the check and asked if she wanted to go to the beach. As we hit the sand, I spun her around and surprised her with a kiss. She was the worst kisser ever. She gave me that straight hard tongue. Terrible, but my hands roaming her sides, and the top of her perky ass let me ignore it.

I grabbed her hand and pulled her towards the ocean. We laugh and played, splashed the edge of the surf, and threatened to tackle each other into the water. We kissed a little more, but her skills didn't get any better. When my hands found her strong thighs and tight ass, I gave up on her stiff motionless tongue and began kissing her neck and nibbling her ear.

She let me lift her dress, squeezing hard on her cool ass, but stopped me when I began rubbing her bushy pussy through her thong. Figuring I'd have better luck with fewer clothes, I made my move.

"Let's swim."

She looked shocked, but excited. I pulled my shirt over my head and dropped my shorts into the wet sand, kicking up into the softer sand where the water could never reach. Brynn giggled, pulled her dress over her head and tossed it up with my clothes.

Her mis-matched bra and panties told me she had no intentions of getting this comfortable, but a few beers and a glass of wine, maybe my award-winning personality, let her open up to me.

In the bright moonlight, her body did not disappoint. Nice full tits, flat stomach, a little curve to her hips and a taut, full ass. I grabbed her, pushing her to the water as I nibbled her lips and felt her body. My cock stirred and swelled in my spandex boxer briefs as we fell into the waves. I played with her body under the water, sucking and biting her neck, feeling every inch she would allow me to. My hard cock pressed against her mound while she wrapped her arms around my neck and kissed me deeply, her tongue finally moving - just barely.

Still a shit kisser, but a fantastic playground of a body, I unclasped her bra and let her supple tits out into the night. She had great little nipples, rock hard from the cold water, little brown buttons that I pinched and sucked back and forth, grinding myself into her. She moaned and grabbed my cock momentarily, then in an instant shoved me back and put herself back into her bra.

"I don't want to do all of this."

"I'm sorry... I..."

"No, it's fine. You're great. Fuck, you're great. I'm just not trying to fuck you on a first date, ya know?"

She was a good girl. No idea why she was never married. From what little I saw; she could have made the right guy really happy.

We threw on our clothes over our drenched bodies, went back to my truck, and I took her back to my house. She gave me a kiss and drove away, sending me a text thanking me for a good night.

We continued talking for a couple of weeks, but I couldn't shake the idea of not wanting to kiss her out of my head. The face, that tongue. I couldn't do it even though her body was incredible. Eventually I told her that I decided I didn't want anything serious with her, to which she wished me luck and I never heard from her again. Like so many others, I see her pop up on the dating apps every now and again, using a bikini picture she took for me on her profile, per my recommendation. Her body was really, really fun.

Date #3: Katie the Giggler

Katie was nothing, but laughs. Tall, curvy, blond in her early 30's, pretty smile and ice blue eyes. She didn't have the best body, or the best face, but she was incredibly fun. I actually went on two dates with Katie and she was the first I willingly broke my "no kids" rule with.

We shared a bottle of wine at a nice outdoor restaurant near a park on a lake. Everything was fun and easy. She wasn't looking for anything serious, which is why when she sent me a message, I went ahead and responded despite acknowledging that she had a kid. After my first several dates, I was very open to just going out and having fun, not taking it quite as serious as I maybe started.

On the date I found out that she actually works for a company who's a supplier for my business. It's a megacorporation so she had nothing to do with anything I dealt with, didn't know any of my contacts, but we shared a laugh going through her company's intranet to put some faces to the voices and emails I've dealt with for years. Dan, my AR contact, was a funny looking man.

Anyway, after dinner we walked through the park, she told me she was "very attracted to me" then said, "I don't kiss on the first date." Ah, whatever. She was fun. The banter was top notch. She dished it out and could take it just the same.

A few days later we agreed to a second date. Another fun experience. We ate, we laughed, and then we made out like prom night in the parking lot.

I walked her to the car, gave her a hug, and said, "You're going to kiss me now because this is the second date."