The 50-First Dates Ch. 21-30

Date #21: Tina the Loss

This was another surprise, in the best ways. Tina was a few years younger than me, with two teenage kids, and a profile that was "meh" at best. She looked pretty and wasn't fat, so I swiped on her. Most swipes go nowhere, hell, most matches go nowhere, so I sometimes loosened my standards to find a needle in the haystack.

This one turned out to be maybe my best match ever, though potentially dangerous and I fumbled it completely.

Tina was fun from the jump. She had a great sense of humor, roasted me perfectly, and dripped sarcasm all over the place. My schedule was busy with other dates so it took a while for me to get her out, but after a few weeks it was on. I still wasn't sure what I was walking into when I pulled into a spot at her favorite sushi place.

She pulled in moments later and when I greeted her at her truck, I was blown away. She was PERFECT. Absolutely beautiful, but not in the high maintenance way. She wore a little makeup and was dressed very casually, but my mind was on fire. She was on fire.

5'6", lean but not skinny, big tits (DD's if I had to guess), a narrow waist, a little bit of hips and a perky little booty. She had eyes that sparkled and a smile that just melted me, wispy sandy blond hair down just past her shoulders and a very sexy half sleeve tattoo running from her shoulder on one arm.

We picked up right where we left off from text and flirted throughout dinner and beers. You could show me 1,000 pictures of beautiful women and I might not rank her at the top, but in person, she just had it. She had me in the palm of her hands.

After dinner I drove us less than a mile down the road to a shitty bar I had found on Google Maps, but the second I walked in I hated it. We found a table and I immediately made the call to go somewhere else. She recommended her favorite dive bar that was across the street from the sushi place and we sipped beer I hate, while playing darts. We laughed over bad date stories and she seemed into me, but I wasn't totally confident. Honestly, I was so blown away by her right off the bat that my mind was clouded.

It wasn't just looks either. Everything that came out of her mouth was perfect. Clearly, it really wasn't, but I just felt a great vibe with her and she was too God damn fun. She was, 100%, girlfriend material.

By the end of it, my mind was so damn fuzzy that I wasn't even planning on trying to kiss her. Even after the bartender asked if we were married and we made a cute couple while she was in the bathroom, I was still unsure. I was scrambled. To my pleasant surprise, I went for the hug and she just kissed me! Nothing crazy and I didn't push it, but it was nice. Cute almost. I was smitten.

We continued chatting back and forth until I scheduled another date for us. This one was special. It was the holidays and she mentioned she hadn't gone to see Christmas lights in years. We had also discussed our mutual love for oysters, so I planned on hitting the best spot in town to eat, then Christmas lights, then find a fun spot to chill at.

Oysters went swimmingly and I ended up with the biggest oyster I've ever eaten. I don't post much on social media, but that one - meat the size of my palm - went straight to Instagram. After finishing off our pitcher of beer, we drove to the lights display. It was a drive through setup where you tune in to an FM station and put through a giant parking lot, filled with lights synchronized to the music. It was pretty cool, but went by VERY quickly, so I tried to find a place to go to next as we pulled out.

Not paying attention, I pulled right into a giant outlet mall just as all the stores were closing at peak shopping season. Traffic jam.

We sat in excruciating bumper to bumper for over an hour, trying to figure our way out of the parking lot. I was totally embarrassed, figuring I fucked up completely, and to top it off, couldn't find a fun spot nearby. I was so focused on the lights I got overly confident with my knowledge of the area and failed to properly plan. We ended up going back to her little dive bar, each drank one beer, and she was ready to go home. Another little kiss, but I felt she had faded.

The guy who's so meticulously planned dozens and dozens of dates at this point decided to wing it with, to this day, the ONE woman who made me think "serious relationship" more quickly than any other. Then again, that was the danger with her.

In just a few weeks of chatting and two dates, I had "love" written all over her. I'm smart enough not to get ahead of myself and am always on the lookout for dealbreakers to protect myself, but every layer of that onion I peeled back, she just got more and more attractive. I'm not sure that I've ever so comfortably vibed with another woman in my entire life. Why couldn't I have met her in my 20's?!

FUCK!

My perception of her fading was reality and her texting became more and more labored. I tried to set up another date and she cancelled. The fading continued. She ended up telling me that she wasn't ready for a relationship and gave me all the standard soft letdown things. I waited a bit and reached out to her again, trying desperately to rekindle something, but another couple of exchanges and she was once again, gone.

Pretty recently I was doing my standard purge of go nowhere women and I stared at her number for a few minutes. Fuck it, I sent her a text. Nothing, as expected. Two days later I deleted her number, something I had failed to do in so many purges before.

It's ridiculous because I know I barely knew her, but honestly it really felt like a loss. Like a relationship was over. I didn't get too sad or anything, but it had that same sort of unfinished business you always have when something ends. At that point, I was starting to feel as if I was actually ready for something serious. Nobody else had, or has to this day, come anywhere close to making feel like opening up to the idea of something true and lasting.

Date #22: Amy the Amazon

My general strategy in making a connection started off as tons and tons of messaging over the course of days and weeks, moving to text, then scheduling a meetup given the craziness of my first date. It evolved into a handful of messages back and forth, spread out over a few days, then securing the date and moving to text to iron out the details. When I met Amy, I was somewhere in between.

We chatted a bit straight away and moved to text pretty quick. She actually wanted to call me to "make sure all this fun would hold up in person." Of course, I passed the test with flying colors and we scheduled a date. Unfortunately, my schedule was full as usual, so it had to wait for a couple of weeks. During that time, I was pretty busy and not responding very quickly.

She actually called me out just before the date, saying she was going to cancel on me, but her friends talked her into giving me a shot. She needed more attention.

For the date itself, we settled on a nice Mexican place neither of us had been to before. She had trouble finding the parking garage I mapped for her, so I ended up meeting her on the corner, talking on the phone to find each other.

I knew she was tall, my height actually, but she was also big. Not fat mind you, rather thick and powerful. Former power lifter in fact. A true Amazonian beauty. Blue eyes, very dark brown hair just past her shoulders, and massive curves in all the right places. I'd later find out, a hint of abs. I stared at her shimmering black stretchy pants as I approached, her broad thighs and ass begging to suffocate me.

We hugged and chatted as we walked to the restaurant.

"You're not 5'11" I chortled.

"YOU'RE NOT EITHER!" she laughed.

We were both right. I round up a little and she rounds down... what I would consider a lot. She's just shy of 6' leaving a solid one inch between us.

Fun was had at dinner and we took a walk through the park. She was very sweet and fun and that potent physique had me intrigued. She informed me as the date grew late that she does not kiss on the first date, so I had to take her on another if I wanted that sort of fun. And I was interested in fun, maybe more.

Second date we joked about me not wanting to kiss until the third date and I even playfully denied her at one point as we took another walk riverside. Maybe 15 minutes later, we were making out. She was a good kisser and feeling her voluptuous body against mine was very arousing. We talked and talked, going on several more dates, but the timing just never seemed to work out for sexy time.

Eventually I realized that things were going to get serious and after my experience with Tina, I had my shields up. I wouldn't let her in. I told her as much and with a few tears, we parted ways.

She reached out a few times over the following weeks and months, and we chatted here and there. One night, she propositioned me.

"How would you feel about getting together for fun, nothing serious?"

"Absolutely!" ("death by snu snu" chanting in my head - Google it)

We caught up over dinner and made our way back to my place. We watched about 10 minutes of a movie cuddled up on the couch and I was in my head the whole time. This felt like relationship stuff. In that moment I got up, and pulled her into my room. She peeled her skin tight striped dress over her head and I tossed my shirt to the floor.

We rolled onto the bed and the thoughts of relationship along with the plethora of drinks in my belly full of food turned against me. Junior down below was completely dead. I played all over her body, holding her massive tits and sucked her perfect pepperoni slice areolas and little button nipples. I ripped all over her voluminous stature, her miles of creamy white skin gave way to my touch and I licked every inch I could before burying beard in her hairless mound. I lapped and tongued, sending several orgasms ("almost 6") through her and my brain was downstairs trying to coax the turtle out of its shell. It just wasn't happening.

She was understanding as, it literally does, 'happen to all guys.' I was embarrassed. Nothing like that had happened to me in forever. Had this been a random hookup, I would have destroyed her. She came so easily it would have been an amazing time, but unfortunately, it just didn't feel right. I don't know if it could be love or any of that, but she's so damn nice and shared so much with me about her struggles in love, I guess I just didn't want the responsibility.

Over the course of the next few weeks, she tried to reach out, but I pushed her to the back burner and eventually stopped responding. I was usually so up front with everyone, but in this case, I was a coward. If there's some chance you're reading this, Amy, I'm sorry.

Date #23: Dana the Desirable

Dana was another risk I took. She was cute in her profile, a mid-30's MILF, but didn't have very good pictures. No full body pic, but I could tell she at least, wasn't too fat. What a pleasant surprise she turned out to be.

She was a bartender at a big fancy hotel and had amazing stories of meeting celebrities. We totally vibed on music, movies, and the important things like values and dating goals too. When we met in the parking lot at my standard Ferris wheel attraction date, I was quite happy with what I saw.

Short and thick, she had hips, tits, and ass for days. Her straight dyed blond hair and big brilliant smile drew me in, while her black rimmed glass gave me sexy secretary thoughts. We ventured across the street and teased each other as I kicked her ass at minigolf.

Dinner at a decent Mexican place nearby went very well and we never lost things to talk about. She was not into the Ferris wheel idea and I learned my lesson not to push it, so we ended up drinking cheap beers on the patio of a loud live music venue, just far enough away so we could carry on a decent conversation. At last call, I walked her to her car and went for the kiss.

She was a fantastic kisser, mixing the soft and strong licks and nibbles with me in perfect unison. My hands roamed up under her jean jacket as I pulled her tighter to me. Her body was firm, but supple, and I was overwhelmed with desire for her.

We kept kissing and my hands kept roaming, eventually I found myself under her shirt threatening to undo her bra as I sucked hard on her neck. Her little moans of encouragement guided my hands down the back of her pants, fondling the top of her cheeks and toying her stretchy thong. We played like this for almost a half hour, my cock drooling with excitement and my overzealous mouth leaving welts on her neck.

She was a bit embarrassed by the picture I took of the marks and we laughed and discussed another date. After a couple more days of texting, she confessed to me that she didn't feel ready for a relationship and wasn't the type of girl who could do casual. In retrospect, things went too far there in that parking lot and I think I made her feel slutty. I kick myself for that one because she really was fun, interesting, and sexy. I could see girlfriend potential in her.

Date #24: Mandy the Family

I met Mandy for our date at my favorite oyster spot. She loved 'em, said she hadn't had them in a while, and I'm always down, so there we were. Upon our hug in the parking lot, she was exactly as pictured in her profile. 40, 5'8", big pretty smile, long wavy black hair, pale skin, a very lean frame but big hips and a juicy ass. Very Italian.

She was sexy as fuck and her body was killer, but as we sat there eating oysters, I kept thinking she reminded me of my sister. Completely ruined it for me. A couple of pitchers of liquid courage and those thoughts faded, so we opted to drive to a bar that was on the way home for both of us to grab a night cap.

Several more beers, lots of laughs and flirting, I knew I couldn't be with her long term, so I angled for a hookup. Like I said, I'm not really a hookup guy, but in this case, I was a little drunk and figured she could be some fun. I didn't get the feeling that she would be into that sort of thing, but we were there so what the hell?

As we exited the bar we walked through the lot and she started walking away from me.

"Where are you going?"

"To my car, I thought the date was over?"

"Almost. I was going to walk you to your car and make out with you first!"

She doubled over with an echoing cackle, repeating my line back to me several times as she approached. I wrapped my arms around her, reveling in her lean upper from, my hands finding their way to her wide hips and we kissed sloppily between the parked cars.

"That was nice."

"It was."

"You're a really good kisser."

"I am. I'm also good at other things."

"What other things?"

"You want to fuck around and find out?"

"Maybe."

"You live nearby right?"

"I do, but not tonight."

"No?"

"No, I haven't done that sort of thing since college."

"This bar doesn't feel like college?"

"It does, but let's not. Not tonight."

"Oh, second date stuff?"

"Probably not then either, I want something serious."

"We talked about not getting too serious."

"I know, but I do eventually want it to be serious."

"I'm not sure I do."

"I guess that's it then. Thank you for the great date. And the great kiss."

"No, thank you. I liked that last part especially."

Giggles, "You take care of yourself, Jack."

Date #25: Maura the Manipulator

Huge risk on this one. I might have been drunk when I swiped her actually. Zero attraction to her face, but I could tell she had a nice body. Maura was a true freckly ginger, 5'7", lean and somewhat athletic, but dressed like an old church lady. Because she was an old church lady.

Ok, so she wasn't old, but she was definitely an old soul, and frankly not all that pretty. She was 36, divorced a couple of years, no kids, and religion was a major factor in her life up until that point. She grew up very strictly conservative, married fresh out of high school, and started her career at the church. Somewhere along the way she lost her faith and turned the skills she developed working with people through the church into a career as a counsellor.

Maura was wicked smart and pretty wise, though she had some major gaps as a result of living such a sheltered existence. She had been exposed to a lot through her work, but hadn't lived a lot of life herself. Despite this lack of life experience, she really worked hard to break me down, digging deep into my past and truthfully, helping me deal with some of the lingering trust issues I had.

When it came to that inexperience, the biggest glaring gap came to a place that I am quite experienced with. Sex.

I took her to my rooftop romance spot that looked over the beach and we shared a bottle of wine. The conversation was good and despite her conservative attire - a standard long dress with a floral pattern - I found her plenty attractive. Her body was wonderful and she had some cute mannerisms. After dinner, we went to the beach just as I had on so many dates before, and popped another bottle of wine, getting more flirty.

There was a bit of a chill in the air and she cuddled up next to me as we laid on the beach and talked. She traced my chest and I rubbed her arm through the conversation, then I rolled to my side into her and lightly kissed her. She reciprocated and I escalated, working my tongue in and out of her eager mouth. For being so inexperienced, she was a pretty good kisser.

The tension grew, along with other things, as I held her and felt her body through the thin cotton fabric of her Sunday best. Her body was the perfect mix of firm and soft, turning me on as I teased the outline of her traditional panty line on her hip. She continued growing more feverish and I hiked up her dress to find my hand squeezing on her alabaster thigh.

Her breathing changed as we got more intertwined and, in a flash, she rolled away from me onto her side. She pressed back against me, grinding my hard dick with her cute perky ass as I kissed her neck and teased my fingertips over her dress, up her stomach and onto her perky C cups. I nibbled her ear and lightly tweaked her nipples through her bra, causing her to let out a loud moan.

I got more and more into it, mixing in some firmer touches along her body and between her legs, careful not to push too far and freak her out by being all over her pussy. Just a graze here and there as her dress continued to rise. Turning back into me, our mouths embraced again and she whimpered in pleasure as I pinched harder on her nipple.

I was fully at attention and out of pure instinct, I mounted her. She immediately froze, pushed against my chest and I jumped off as if she were electric.

"I'm so sorry!"

"No, it's not you, it's me."

"No, I made you uncomfortable."

"I'm not very experienced and my last experience was..."

"Say no more, we don't have to talk about it."

"No, I want to. It helps and you're making me feel safe."

She went on to tell me how she had only been with three men before me. Her husband, a guy she dated a year prior, and her last experience - being drugged and date raped.

I listened to the horrific story and really worried that I had frightened her. At that point I decided to call it a night. We packed up and went back to our vehicles. As I kissed her goodnight, she commented that we should have stayed on the beach. I made a joke about getting more comfortable in my truck and to my surprise, she eagerly accepted.

I opened the passenger door and let her in, then circled to my side and we started making out. My hands were being more cautious and respectful, then she started pulling one up her side and onto her breast. I resumed playing with her nipples and she got hotter and hotter.