The 50-First Dates Ch. 01-10

She laughed and we kissed. It was lightning. She was a great kisser. She started to giggle and asked if I wanted to sit in her car and talk a bit before ending the night.

"Sure, I'll make out with you in the car, Katie."

"That's not what I meant!"

"Yeah right, let's make out!"

In her car we got a little frisky. Everything PG-13. The more we kissed, the more she giggled.

"I haven't made out with anyone in a long time. This feels like high school!"

And it did. A lot of my dates did. Her comment was a brain worm that to this day I think of when I'm on dates. It was so much fun. The laughs, the flirting, the sexual tension. I revel in it.

We kissed and kissed, I made fun of her for "giggle kissing" and we kissed more. My hands found my way up her shirt a bit, then down the back of her jeans, fondling her round ass in her silky full coverage panties.

"Grannie panties, but sexy granny panties" she joked.

Totally ok in my book, I never really liked thongs anyway.

As things were about to get hot and heavy, the windows steaming, our fun time was interrupted by a group of 'kids' carrying on outside the car next to us. My half-hard cock dreamt of her mouth as the moments between our tonguing her comments were more and more suggestive.

"Next time we need to find a place a little more private."

I agreed.

Unfortunately, over the next week her texting slowed. Eventually she admitted that she wanted more than something casual with me and I had to turn her down. I did not want to date a woman with kids, even though her situation may not have been that bad seeing as how she was kid-free every summer and her daughter wasn't due back for another month. Truth is, she wasn't attractive enough for me to go down that path with.

Date #4: Crystal the Good

This one was a failure and I learned a lot. I had all of the momentum of a series of great date performances behind me and I got cocky. Every date was all over me, but Crystal was not. That's not to say she wasn't into me, because she was, but I got too aggressive, miss-timed a kiss, and scared her off. I made this mistake a time or two after, but now have it completely dialed in.

She was a late-20's redhead. Long straight light auburn hair, milky pale skin, gorgeous smile, petite pear-shaped body with a nice fat ass and thighs. Probably 5'3" and maybe 130lbs. She was hot. She was also as sweet as she could be. Had a similar relationship experience as I did, catching her husband cheating and being totally broken.

We had a great date. Burgers and beers, kicked her ass all over the barcade, and all signs pointed to something happening going forward. Perhaps not all signs. In retrospect, I did notice a lack of reciprocation when I made physical contact. Not that she was repelled by me, or I was getting super handsy or anything, she just didn't touch me back. I playfully shoved her when playing a game and nothing. I guided her as we walked with a light touch on the back as we changed directions. I offered myself to her by closing distance, but she never quite broke the barrier with me. It's those little things I've grown to read with incredible accuracy.

I walked her to her car and was stopped for the standard end of date embrace. I kissed her. She kissed back, but I tried to REALLY kiss her. The second I parted my lips I felt she wasn't into it. I stopped, thanked her for a great night and went home.

Like with all of my dates, I timed her commute back and sent her a text making sure she got home ok. She did and thanked me for a good night. We texted a few more days, then she disappeared. That happens a lot with online dating, but in this instance, I think I know exactly where it went wrong.

Date #5: Nikki the Catfish

A disaster. Nikki was 40, tall, 5'9", and kinda cute, with short, kinky, poorly bleached hair and tan, but lots of freckles like I love. She was fun to talk to and her body looked good online.

My first 'fatfish.'

Walking up to the seaside bar, I almost turned around as I saw her. I didn't realize I was going on a date with someone who was a lineman on the practice squad of the New England Patriots.

She was a BIG woman and unfortunately, she made eye contact before I could bail. I had driven almost an hour to meet her, so I decided to make the best of it. With her 'decades of smoking' raspy voice, she greeted me as "funny man" and wrapped herself around me.

What's funny is despite being big, she actually carried it pretty well and didn't look totally terrible in her green maxi dress. In a different setting, late at the bar, she might be someone fun to fuck around with after last call. So, I got drunk.

I got really drunk. I had 11 Coronas with my fish tacos and we had some laughs. As the sun set, I realized I had drank way too much and no way should I be driving home. I switched to water and we took a walk on the beach.

I was taking salsa dancing classes at the time and I showed her a few moves. We kissed, which was actually pretty nice, but even with the beer goggles, I wasn't attracted. We ended up at another bar down the beach for several hours screaming at each other over a live band. We walked back up the beach, I walked her to her car, and we shared 'lip only' kiss. As I walked away, she said, "maybe another date?"

I flatly responded, "Maybe not." Got in my truck and left. She didn't message and neither did I. about 9 months later I saw her profile pop up again, this time with very honest pictures. I'm guessing this sort of thing happened to her a few times.

Date #6: Virginia the Ill

This girl was a mess. Late 20's, very pretty, really skinny, but had decent tits. We talked for a few days, set up a date, and one night she surprise-invited me over. She was drunk.

I met her out front of her apartment where she was letting her dog out. No makeup, but at 5'5" with pretty layered and highlighted hair, her cutoff t-shirt and loose sweatpants falling off her tight little body looked damn good to me.

We went inside, cuddled on the couch and began talking as she flipped through Netflix. We settled on stand-up comedy, but quickly moved to making out. She was a good kisser. Our lips and tongues were well matched, and my fingertips weaseled their way to her sweatpants, finding the top of her lacy thong against her soft, taut skin.

"I know how it looks because I invited you over, but I we are not having sex tonight."

No problem for me. I was ready with a rubber in my pocket, but she was fun and sexy, so I didn't mind waiting a bit. We played around a little more, my hard cock digging into her lean frame making me very, very horny.

Eventually things calmed down and we cuddled, finishing the show. And, she was asleep. I tried to wake her up, but she wouldn't budge. I gave her a kiss on the forehead and she started snoring. I let myself out and went home, sending her a text along the way explaining she fell asleep so I left, reminding her to lock her door.

The next day we continued texting and all was good. The day before our actual planned date she mentioned needing to get "another treatment." Treatment for what?

Cancer.

She had ovarian cancer.

I was blown away. Part of me felt deceived, but I guess I understand that's not exactly a great opener for your online profile. It was treatable, but she started in making jokes about "maybe dying" that made me uncomfortable. I went ahead and kept the date, though the thought of courting a woman who was dying stuck deep in the back of my mind.

I picked her up at her apartment. Before leaving, we shared a bottle of wine and she really started to open up to me. Her past was full of abusive relationships and some of the things she told me were downright frightening. I was starting to feel like she was really looking hard, not for me, but anyone who would be there for her, treat her well, and protect her as she "maybe" died.

I pushed the thoughts from my head, dedicated myself to a fun night, and we went out to grab some oysters. We got a bucket and she ate exactly two. Her appetite was completely killed by her cancer treatments. I tried to end the date right there, but on the way back to drop her off, she insisted we go to a cigar bar. She really was speaking my language, so I agreed.

We had a good conversation at the bar, then sat on a couch to finish our cigars and cocktails. She dangled her feet over my legs and I began rubbing her ankles. I'm not at all a foot guy, but if I was, she had really, really nice feet. Caressing her ankles, I found a little spot just below her calf that she missed while shaving. I teased her a little bit, playing with it, and she kicked her legs off of me, welling up with tears.

The final nail in the coffin.

I'm playful. I joke and tease. Despite my best efforts to laugh it off because, let's get real, it was NOT a big deal, she shut down. I knew right then and there I had to end it. With our cigars dwindling, she made a full recovery and we drove back to her place.

I pulled in, walked her towards her apartment, and said, "I had a nice time, but I don't think this is going to work. I know I upset you with that little spot on your ankle, and I'm sorry. But I know me. I'm going to play like that. I'm going to tease you. And I'm really going to hurt you. I don't want that for you."

The tears rolled down her face and she stormed off, yelling something about "emotionally unavailable men" slamming the door behind her. I wish that was the last time I made a woman cry on a date.

Date #7: Bethany the Dud

I went on a few dates with Bethany. She was another mom, but her kids lived out of state with her parents as she got her life together after relocating to Florida a couple of weeks before we matched. That timeframe was somewhat extended and she wasn't in a rush for anything serious, so it worked.

Bethany was in her early 30's, 5'4", super dainty features and as I would find on our first date, a big ol' butt. She had long brown hair, liked heavy metal music, but dressed like she was going to church every date. I liked her. The banter was strong, she was fun, and her big brown eyes were inviting. She was very pretty.

Our first date was pretty fun. I found a really nice rooftop restaurant over-looking the beach. It ended up being a place I take most dates who live in that area as it's romantic and after a few glasses of wine, the beach almost begs for a little frolic, tease and tickle.

Right off the bat she spilled her red wine all over her white dress. She was so nervous. Sweet, innocent. I joked with her and calmed her down, we shared a nice meal, and walked the beach. Playing in the sand as the water cooled our toes, I thought of my date with Brynn. Similarly, I went aggressive, just grabbing and kissing her.

She tongued me hard and deep, perfectly swirling her tongue around mine and nibbling my lips each time we broke. My hands roamed up and down her body, not being too frisky, more teasing that I could just take her at any moment. She was driven wild. She began directing my hands to her ass.

Grabbing big handfuls of her firm, rotund rear end, I pushed my hardening dick against her. Her little high-pitched moans sent me into a frenzy. I bit and kissed her neck. She grabbed my member through my shorts, tugging it hard against her. I pulled down the top of her strapless dress, unveiling nice sneaky big hangers, with sexy ghost nipples that perfectly matched her pale skin. I lifted her up and gnawed back and forth between them, her whimpering moans growing louder and louder.

"Oh shit!"

She slapped down hard on my shoulders and flailed herself off, falling back on her ass in the sand.

I turned to see a family approaching from a distance with flashlights - crab hunters, I'm guessing. I helped her up and she pulled herself together, sheathing her big soft tits and giggling as we walked back up the sand. We held hands and I noted that her tiny hands would "make my cock look so big!"

And, eventually, it did.

We texted a lot after that date and I figured I might have myself a little girlfriend for a while, not that I stopped dating or anything. It took a few more weeks for our schedules to align and I planned a fun evening kayak excursion with a guided group.

Meeting for dinner at a spot along the way, the service was terrible and we almost missed the boat so to speak. We ended up taking our food to go and ate as I broke many traffic laws getting to the marina for our tour. We made it.

It was a lot of fun. We had a few moments where we could hide a little bit from the group, a place where we swam and kissed, teasing each other under the water. I drove us back to the restaurant where we met and we started making out heavy in the front seat.

The bar was hopping and there was a lot of people milling about, but our spot was secluded enough to play a while.

I pulled her bikini top down and dove into her milky skin, finding her tiny nipples with my tongue and nibbling them hard. She moaned louder with each successive bite, eventually grabbing my hand and placing it around her neck. She liked it rough. Not as innocent as I originally thought.

I moved off her tits and kissed her, pushing hard on her throat. She whimpered loudly and I squeezed tighter, her kissing became rough. She bit on my lips and I placed my other hand on her neck, fully choking her. She pushed back, gasped, and rammed her tongue into the back of my mouth moaning hard.

Keeping one hand on her neck and modulating my grasp, my other hand moved down to her thick thighs. Teasing and tickling, my fingers danced to her warm center. At first, she spread open, allowing me to rub through her shorts and bikini bottom. She writhed and breathed into my mouth. I started to slip my finger up her shorts and she stopped me.

"I'm on my period. Let me touch you."

I'll never say no to a good time, so I pulled the string from my trunks and sat back. She stared into my eyes as she stroked me through the thin fabric. She grabbed the front and stuck her hand in, gripping my shaft and tugging lightly.

"Ooooo it's thick."

Fully at attention, she pulled me out, leaned forward and took me into her mouth. She sucked briefly as I played with her large, exposed bosom, then the rumbling of a Harley starting next to us killed the fun. We both jumped and she got freaked out.

"Would you hate me if we picked this up next time?"

Of course not. It was fun, but definitely uncomfortable anyway. We pulled ourselves together and kissed briefly, then she got into her car in took off.

Our last date was a complete dud. I was exhausted from going out the night before and she wasn't feeling well either. We ate dinner, discussed another date, but my dating schedule was really ramped up with exciting new matches so I told her I wasn't feeling it any more. Plus, I knew her kids were about to come live with her and I didn't want to sign up for all that.

Date #8: Angela the Head

We matched just before I was trying to go to sleep one night and chatted for a few hours. She was a ton of fun. 26, hot, and exciting. 5'6" a modern Joan Jett looking dyed black hairstyle, pale skin, a smattering of freckles, various random tattoos, and a super cute feisty smile. We planned a date a couple of days in the future and moved off the app to text before going to sleep.

She loved to text and never slept. I woke up that next morning to a couple risqué pictures of her holding her tits in 'handbras' and wearing short athletic shorts, showing off her myriad of odd little tattoos. I in turn, made jokes and teased her, trying to instigate more.

She didn't disappoint. More handbra pics, ass shots in pink boy shorts, a full nude with emojis covering the fun bits - every one of them with a messy backdrop of dirty laundry and makeup implements reflecting in the mirror. I sent her a picture of the base of my hard cock that night, the rest hidden in my boxers. We flirted hard and I was excited for our date.

Angela didn't drive so I had to pick her up at her shitty apartment that she shared with four guys. Her situation felt strange, but I found out later that they each had their own rooms and she was the only one who had her own bathroom.

I told her I was arriving early and she indicated in her texts she was very nervous. I tried putting her at ease and felt my own nerves explode when I pulled into her parking lot. It was VERY sketchy. I wondered if I was being catfished and about to get robbed when she popped out the door in a classic little black dress. Little, very little. Skin tight. She spent the entire night pulling it down so her ass didn't hang out.

She had a plump ass and a little more than handfuls on her chest. A sexy youthful body that could double for any girl in those casting couch pornos. She was hot.

I took her to a little dive bar for burgers, something she mentioned early on that was totally her thing, and then we took a walk towards the beach. Along the way we stumbled upon a free outdoor concert with some decent 70's cover band. I bought us a couple of beers, she smoked a cigarette, and we played and made out for about an hour as the sun set, pausing only as she danced to a few of the songs and I stared at her hard nipples, unrestricted with no bra.

I suggested us hitting the beach and after buying her a Sno Cone, we walked down to the sand. She finished, we kissed, then we walked to the water and play fought like kids. It was a lot of fun. I was all over her soft ass as we made out and even though there were some people around, I lifted her dress and rubbed her pussy through her black lacey thong under the cover of darkness.

She turned and pressed her ass against my girth, but stopped me from sticking my fingers in her panties. Another one on her period. It didn't matter, she was an easy puzzle to solve. I had her cumming pretty quickly and just as quickly, becoming embarrassed.

Not embarrassed to the point of shame, but rather shocked and a little sheepish that I was able to do that so quickly. "it's probably because you're old and have fingered a million girls" she joked. In reality, I do have some skills, but her buttons were just easy to find. At that point she went into good girl mode and we just flirted and talked while walking the beach.

We climbed a lifeguard tower and sat cuddling watching the lights on the pier in the distance and listening to the ocean. I was getting tired, so I figured I should end the date, especially since it didn't seem any sort of sex was on the table. Helping her down from the oversized chair, I teased that next time I was going to have to really make her cum.

"Next time, huh? You think you've earned a second date?"

"I don't think, I know. Just imagine what we could do when we're both comfortable and you're able to have sex."

"I'm able."

"And I'm willing. Bust out the old towels!"

"Nice try! Not tonight!"

She shoved me back and ran towards the staircase leading off the beach. I chased her and we held hands walking back to my truck. More flirting as we drove back to her place and when I walked her to the door and gave her a kiss she said, "just come inside."

Everything was dark and nothing stirred as we made our way through the run-down building to her room. Each room had its own deadbolt as the apartment was an old house, converted into a communal living space. Entering her dark, messy room, cloths and bullshit piled up everywhere, she cleared her SquishMallow collection off her small bed, flipped on a string of Christmas lights that ran haphazardly halfway around her room and down the wall, then invited me to make myself comfortable on her, while she went to the bathroom.

I sat there looking around, thinking to myself, 'what a shithole' and she came out in nothing but her thong, the light from the bathroom highlighting her silhouette. I pulled my shirt off and she climbed on top of me, grinding herself against me and pulling on my shorts. I unbuttoned them and she pulled them down, making the point to readjust my boxers to keep my granite manhood in place.