The 50-First Dates Ch. 61-70

I know the numbering is thrown off here, but I had to square away my last minute decision to redact my original Date #60. Just so happens that my vacation a couple of weeks ago yielded a story so I threw it in there and wrapped things up at the end.

Date #60 - Cynthia the Brick

Sing along with me... "She's a brick.... Hooouse."

Boy was she. 5' nothing, built like a Mack truck. Cynthia looked very pretty in her photos and even prettier in person, but god damn was she thick. Crazy thick. Like a sexy Mrs. Kool Aid Man crashing through walls - "Ohhh yeah!"

When I walked into the seafood place and saw her at the table, my heart sank. She looked too fat, but once I got closer I realized it was all in the right places and she was a force of nature. Early 40's latina with straight shoulder length hair, blond highlights, and despite having infinite curves, a near completely flat stomach. In retrospect, I'm have to assume there was some lipo on the waistline because her body was damn near cartoonish.

We ate, had some laughs, and my attraction was growing. She was super fun, totally down to earth, and wildly sexy. Touching on more serious subjects, I hit the mother load of bad news. Previous marriages.

Truth is, we all have some sort of history and when you're dating in your early 40's, you're bound to encounter a divorce or two. Cynthia, however, had just buttoned up number 4.

Check please.

Going through the stories, none individually would have been giant red flags, but as a whole, this was a woman who couldn't handle being alone and was aching for commitment. I'm not that guy, but after the initial shock wore off I had her talking about not committing and on the verge of offering a friends with benefits situation.

When we finished eating, I walked her to her car and we seemed to be on the same page about taking things slow and not being in any rush for exclusivity. We kissed, I fondled the miles of firm curves and she pressed herself hard into me. It was great. She was sexy as all hell and apparently open for something more casual so I was pretty excited.

That illusion wore off in the coming days. She didn't totally come out and say it, but she caught feelings straight away. The tone in her texting changed, she was more aggressive in frequency, and even threw out a few triple texts. We had set up another date for the following weekend, but by our 1-week anniversary (I'm guessing she marked it on her phone), I knew I couldn't see her again. Last thing I needed was a stage 5 clinger.

I did give her a bit of a chance though, slowly fading on the texting to see if she would calm down, but as you might expect, it had the opposite effect. She responded immediately to every text and more double/triples. Finally, she ended up calling me and I had to tell her the truth.

"Sorry, but I think you're meant for fast and serious. I'm more fast and fun."

She took it well enough, though I did hear her voice crack a bit as she wished me luck and said goodbye.

Date#61 - Carly the Lesbian

Carly was one of the good ones and an interesting woman. She had spent her youth in standard heterosexual relationships, then her 20's and 30's only dating women. I was the first man she dated in almost 20 years.

Her profile was mediocre, but when I eventually met up with her, I knew immediately she was one to keep around. Super cute, spunky, about 5'3" early 40's latina who, without the bangs and highlights, could definitely have been confused for Rosie Perez (just with a much better tooth to gum ratio). She had a bit of curves and was just a little spicy from the jump.

We ate sushi and played in an arcade, another of my standard dates, and ended the night with a little bit of kissing - nothing spectacular. On our second date, we ate Mexican and drank tequila, then after watching a car crash when we were walking back to her car, made out hot and heavy, my hands deep in her pants snatching up her soft smooth ass.

One thing that was really nice about Carly was her proximity. As luck would have it, she lived less than 10 minutes away. Once our third date ended in my bed, the remainder of our rendezvous were mostly impromptu booty calls and there were many over a few months.

It started off as if we were heading towards a relationship, but she had a bit of a masculine energy that turned me off. I cannot exactly pinpoint anything specific, but at the time I knew pretty quickly that she just wasn't for me. She was a fun hang, a sexy little thing, and almost like a bro. A cute female bro who loved pussy, but needed some dick.

I established we wouldn't be more than friends after maybe the second or third time we fucke, which often ruins the physical dynamic, but in this case it may have improved it. We had a ton of sex. Usually two times per meet up, sometimes three, as many as three times per week. I bet we fucked 100 or more times in the few months we talked.

It was a bit of a learning experience for both of us. I taught her how to suck dick and she improved my fingering game significantly.

"Touch me like this... softly."

She grabbed my hand, lightly rubbing her freshly shaven pussy with her fingers intertwined with mine.

"Don't use any pressure, just rub around the outside until you feel it getting wet all over."

She releases my hand, running her fingers through my beard and pulling me in for a deep, forceful kiss.

"You feel it getting wet? Mmmmhmmm... make circles... yeah, now push a little bit."

My fingers drip with her excitement as I spread the slick essence around her womanhood.

"Oh, that's good, I like that pressure."

My palm is pressing on her pubis while my fingers work her at an increasing pace.

"Yes... good..."

I lean forward, taking her big dark nipple into my mouth, sucking back her little teardrop breast, slurping until it pops free, springing back to her chest.

"Rub harder on my clit."

My middle finger presses in, finding the hard little pearl, and gently applying pressure, continuing the larger circular motion with my hand.

"Up and down now."

My slathered hand works her entire pussy up and down, with my middle finger stronger and more stiff against her clit.

"YES... just like that... you might make me cum... faster!"

My pace intensifies as the scent and sound of her arousal fill the air.

"Go inside..."

She grabs my hand, halting my motion and pushes on my fingers. My middle and ring fingers plunge inside, curling up to her G-spot.

"That's it! YES... fuck yes!!! Harder!"

Pressing hard against the firm ribbed flesh of her sapphic canal, mashing her G-spot, I work deep and fast, building a froth that drips off my knuckles.

"JUST LIKE THAT JUST LIKE THAT.... UUUUUUHHHHHH.... JUST LIKE THAT!!!"

She shakes as the writhes and gyrates against my powerful digits, her flesh jumping as she orgasms under my relentless motion. I slow and gently draw circles with my fingers as I withdraw, returning to the outer rub that got her so hot to begin with.

"Whew!" she exhales, "Now how do you want it?"

"Like last night."

She smiles, leans forward and bites my lip, running her fingers through my beard. I roll to my back and she follows on top, then kisses down my neck to my chest, nibbles my stomach and continues down to my eager meat. With a few slurps and hand twists, the techniques I taught her just days before, she turns around and slides her legs under mine. Leaning forward, she presses her sopping mess of a cunt onto my cock, slowly grinding into it as I grip firmly onto her cute brown cheeks, admiring the white tanlines from her bikini bottoms.

Reaching under, she grabs my shaft, pressing it against her heat and grinds up and down slowly before moving forward and directing my helmet inside. Turning her hips down and clenching hard, she strokes my oak with her hot velvety pussy. I squeeze her ass and rub to her hips, groping her and pulling myself into her depths.

She sits up, arches her back, grabbing her ass and spreading herself while leaning into a rhythmic motion. Slowly back and forth, up and down she works to grind the base and deliver a full stroke nearly allowing me to fall out. I watch as her pussy stretches inside out with every motion and her cum builds at the base of my tree.

"Fuck me fast and make me cum." I demand as I reach up and grab a handful of her hair, pulling her down over me completely.

She begins grinding harder and faster, laying on top as my as my hands roam her soft body, clamping hard on her tits as her hips spin into me. She sits back up, bouncing up and down as her bright tanlined ass slightly dimple at the bottom of every squeeze. She falls forward, rocking back and forth quickly down my entire length as I use my fingers to push the base so it doesn't spring out of her tiny hole. I slap hard on her ass as her pace intensifies, leaving a perfect hand print welt that fades into white as I clamp hard on her soft flesh.

"I want it all!" she moans, springing forward and turning around, straddling in a scissor position, jamming me back inside. Clawing my knee she holds onto it like the rudder of a ship as she violently grinds back and forth, then slides up and down at a feverish pace, pelvis to pelvis taking me as deep as possible and bringing me to the verge in just a few seconds.

"Yeah, like that... you're going to make me cum."

"Mmmhmmm... MMMHHHHMMMM..." She bites her lip and hugs my leg tightly as she pulverizes herself on my rock hard girth.

She's relentless as I cum. So ravenous that my orgasm was shattered by her fervor. I came hard, but barely felt a thing and she worked herself over until I softened and fell out - a mess of cum and sweat between us.

"Did you even cum?"

"Yeah, a long time ago."

"I didn't even feel it."

"You were going pretty hard."

"Was it even good for you?"

"We've done better for me, but it was good for you."

"You almost made me cum again."

"Damn, so close."

"I've never cum from a dick."

"Never?"

"Never, but it's not like I have a ton of experience."

"Yeah."

"You did well with your fingers though."

"I had a good teacher."

"That wasn't weird or uncomfortable was it? I know I just kinda took over."

"Hell no, you made my job easy. Take out the guesswork. Now I know."

"You do. And I'm going to test you."

"Give me another half hour and you can test me again."

"I'm meeting up with some friends for brunch, so I'm going to take off. Should I come back tonight?"

"See you at 7."

We had a great time for those few months. Nothing serious, just enjoying each other for a few laughs and good sex. Come to find out, she's actually friends with an acquaintance from years ago - one of the most beautiful woman I've ever seen in my life, like Nicole Kidman with a nice fat ass.

I ended up calling it quits once I had another, more tempting option in the works. Carly hit me up when she knew I'd be on my way home after work and offered to pick up some pizza on her way over. I declined, told her I was going to go a different direction. She said she respected that and ended with, "I enjoyed you."

Date#62 - Tory the LinkedIn

This was kind of a funny one a midst a handful of completely forgettable dates during my time with Carly.

Tory was a cute chick, mid 30's, long straight brown hair, a little chubby, and with great big tits. Not may favorite body type, but she was smart and fun, with certainly no lack of sex appeal. We chatted briefly online and I set up a date for just a few days after matching.

Everything was accurate and as expected during the initial meetup. I was thinking fuck buddy by the time our drinks came and by the end of it, I was thinking career adviser. We met at a strange time for both of us.

My job was in flux after our big buyout and my position was wildly changing. I was starting to feel trapped between doing what I know is right for the business and doing what I knew would be better for my career. In a perfect world, those two things should align, but they often don't. Likewise, she was several months ahead of me in corporate takeover of her own and we were both fighting for changes in our ERP and CRM systems.

Once we started down that path, our semi-romantic dinner turned into a free-for-all vent session about clueless executives and spineless leaders. That's not to say there wasn't a little flirting, and we did make out a bit at the end, but the vibe was more LinkedIn than Tinder. We even joked between kisses that we should add each other on LinkedIn and start a professional romantic relationship, or an "out of office romance".

We both knew it wasn't going anywhere, but a good vent session and parking lot make out isn't a terrible date. I texted her to make sure she got home, she texted thank you, and neither of us ever texted again. We also didn't add each other on LinkedIn.

Date #63 - Liana the Dime

No exaggeration, Liana was one of the most beautiful women I've seen in my entire life - by far the most attractive woman I've ever dated. Physically flawless like she was built in a lab. I honestly have no idea why she was into me. I mean, I date above my level regularly, but this was ridiculous. She was movie star hot and I don't exactly have dating movie star looks, money, or power. She was a perfect 10, a dime, and my sweet spot is usually in the 6-8 range. But whatever, the good lord was looking out for your humble narrator during this time. God bless him.

Her profile was shitty, pictures lackluster, but she looked good enough for me to roll the dice on and I'm glad I did. We initially had a pretty solid conversation over a few days, then switched to text, and just as I'm trying to set up a date, she disappears. Oh well, it happens, and at this point I have no idea how hot she is.

Out of nowhere a couple of weeks later, she texts me as if nothing happened. I called her out, she apologized, and since I just happened to have nothing better to do that night, we set up a date. She picked a place near her which later I found out was literally across the street from her apartment; a bit of a flag for her level of maintenance.

When she got out of her car in the parking lot I damn near jumped out of my skin. 5'7", blond hair, tan skin, tiny body, perfect D's, long legs, and a hot little bubble butt - "cause I'm Brazillian." She was in a modest, but form fitting and somewhat short sleeveless white dress, fancy strapped heels, and matching french tips on her fingers and toes. While she was Brazillian, she had a very Eastern Bloc look to her - my first guess was Ukrainian, given my previous dates with a few of them.

Amazingly I didn't allow myself to be intimidated by her and I knocked it out of the park on that first date. I had her giggling and laughing, while at the same time getting pretty flirty without crossing any lines. Honestly, I was a toned down version of myself in that regard because, well let's be real, I definitely was intimidated.

And, to be fair, she was also really hard to read. She was quiet and reserved, paused and considered everything she said, and gave off a bit of an aristocratic energy that went beyond the normal vibe just from being that attractive of a person. There's also the fact that she's foreign so sometimes words and phrases don't always translate properly and her accent could get in the way here and there too.

While I hadn't done much to break the touch barrier up until that point, I threw caution to the wind and went for the kiss at the end of the date.

"I had a good time."

"Yeah, me too."

"Good, we'll have to see about another date."

"I'd like that."

"Ok, I'm going to kiss you now."

Most certainly not my smoothest, but I had no idea what in the hell was going on between her ears. She smiled, gave me an "Oh really?" and then wrapped her arms around my neck and we kissed.

God she was a terrible kisser.

Just gives you nothing to work with. Not a lot of motion, barely any tongue, no lip sucking, or anything really. So, at least I knew at this point she wasn't actually perfect and maybe I could coach up her kissing technique.

We texted over the following days, loosely planning my pre-packaged lake park date I've done so many times I'm tired of telling you about it. Aaaaand, she's gone. She disappears for another two weeks.

It happens, no big deal, but then she texts me again out of the blue apologizing and giving a pretty weak excuse about working too much. I'm guessing I wasn't the only guy in the picture, but that's fine because I was still fucking Carly and going on dates with other women too. Just how things go these days.

We do end up on that next date and all goes well for the first half, then takes a bit of a detour on the second half. After dinner, I tell her we should take a walk in the park and she agrees. As we're making our way in, we hold hands and I'm thinking things are going really well. We see the remnants of a farmers market in front of the trio of bars I usually end this date at, with a handful of vendors from that day still there selling some wares into the evening.

As we're window shopping, she starts asking about a bracelet. She knows it's a knock off Cartier and starts describing to me and vendor how the clasp is different and a few other details. Interesting. She's definitely used to getting some of the finer things in life. Then as we walk up to the lake and start down the path, she says, "I'm not walking all the way around."

I was a little shocked. That's always such a great time on all my other dates. Gets the blood pumping a bit, it's a good opportunity to get a little frisky along the way and of course, easy to talk without many distractions. I just went with it and we walked a bit, turned around, and went back to our cars, where, once again, she was a shitty kisser. Still a total smokeshow, still a terrible kisser. Which of course, had me wondering about sex.

For our next date, we did a standard dinner and made it a shorter date because she had to get up early the next day. Tacos, tequila, and makin' out in the car.

More flags arose. She asked me about my dating life, which is fair, and I'm honest, but I got some hints of jealousy. She then proceeded to tell me that she lied about her age on her profile because she was "tired of old men" reaching out to her. I've been down this road before, so I held my breath... Liana wasn't 42... she was 47.

Wow. Truth is, had age never been discussed, I would have pegged her for late 30's. Top tier genes.

She also revealed that her tits were fake, which I suspected, and she wasn't going to be able to see me for a couple of weeks because she was getting a completely unneeded face lift. At that point I started to wonder what else wasn't real, but she said the boobs were the only thing she's ever had work on and the face lift was one and done. Based on everything I had seen, and will see later, that's probably the truth.

We made out in the car. She still sucks at kissing, but I let my hands roam a bit, spent some time nibbling on her ears and kissing her neck. Rubbed up her smooth, tight thighs, teasing under her skirt a bit and didn't push it too far, just enough to turn her on. Eventually she kicked me out of her car and we parted ways.

Just like she said, we didn't see each other for another few weeks. She sent me pictures every few days of her face wrapped up like a mummy and we talked about seeing each other again. Eventually that evening came and she invited me over.

Given her state, I honestly didn't expect sex that night. I just went over to sip some wine, watch a movie, and try to grow whatever it was we had between us. I wasn't that into her personality, but a woman that hot is like a drug. You get a little taste and it can consume your life.

And it only got worse after that night.

We drank a bit, she complained about her face hurting, her dog barked at me the entire time - even when she locked him in her room, and eventually I just went for a kiss. She accepted and things got hot and heavy quickly.

She was wearing a loose orange knit style tank top and white cutoff jean shorts that weren't tight, but highlighted her little bubble butt perfectly. As we kissed, I flirted with my fingers running up her shirt a bit and down over her crotch. She spread her legs for me and I slipped up her shorts, running down on the crotch and massaging her damp hilt under her black lacy thong with the back of my fingers.

She unbuttoned her shorts and I pulled them down from the crotch, leaning forward and kissing her toned stomach and rubbed her pussy with my thumb. She began caressing my straining piece through my shorts. I popped my button and pulled myself out, her delicate fingers gripping tightly around and stroking me gently. At last, we found something sexual she's good at.

"Do you have anything?"

"Anything what?"

"A condom."

"I honestly wasn't expecting to have sex tonight."

"It's ok, maybe just a little bit."

"Like, just the tip?" I laugh.

"Yes, maybe just a little."

And with that she climbed on top of me and rubbed her wet panties over my steaming hard cock. I reached back, cupping her perfect ass, and pulled her thong to the side, feeling her little slickness glaze my length. She reached under, guiding me inside.

"Don't cum inside me."

"I won't."

"Are you close?"

"No, we just started."

"I just want to make sure."

She slowly moved up and down, her perfect little pussy gliding my meat at full length. I lifted her shirt up over her tits, exposing their perfection. Completely natural in look and feel, fifty cent piece areolas nearly the color of her skin, little eraser nub nipples and a smattering of freckles across her chest. 10/10.

I pawed all over her body as she worked herself over my girth.

"My face hurts."

"Is this too much?"

"No, it feels really good, but it's too much."

"Do you want me to finish?"

"Are you close?"

"I can make it happen."

"Ok."

I focused really hard on just how fucking sexy her body was and definitely hurt her a little more when I met her motion to make things a little more aggressive for me to climax more quickly. Another couple minutes and I gripped her tiny waist, lifted her off of me, and sprayed the both of us.

"Did you cum in me?"

"On you probably, but definitely not in you."

"Ok."

She dismounted me and left for her bedroom, her perfect ass sticky with my cum, bounced with every step. Returning a few minutes later in silky pajamas, she immediately kicked me out.

"You have to go now."

"Oh, I figured we'd finish this wine."

"No, you go. I don't do overnights this early."

I couldn't help but chuckle to myself. Oh, so THAT'S how that feels? I'm guessing it's different when I do it to a woman, but for me, it was like this smokin' hot chick just used me for sex and it felt quite wonderful.

We talked about seeing each other again, but it was complicated. That bit of exertion from less than 10 minutes of sex, pushed back her recovery a few days at least. Then, I had a camping trip with friends for a week and we already had some minor scheduling issues. To my surprise though, she paid me a special visit the day I was leaving for my trip.

She texted me early asking when I was leaving, then asked if she could see me before I left. Getting laid before camping for a week is always a good idea, so I jumped on the opportunity.

Taking a massive detour on her way to work, she came over looking incredibly sexy and very professional. Blue dress pants, white blouse, face looking totally healed (and exactly how she looked before she got the surgery), tall heels, and makeup on point.

We sat and chatted on the couch for a bit before she hit me with another one, "we need to have sex now because I have to go to work." I swear, her communication at times was like talking to a guy. She was the best in so many ways.

We start to play a bit and I kissed her neck at which point she stopped me and said she's still in a lot of pain. We didn't waste any more time. We both just stripped right there on my double recliner and she climbed on top, panties on the floor, but matching bra still on. Grinding her hot little honey pot on me got me rock hard in an instant and she helped inside as I unstrapped her bra.

"Don't cum in me."

"Don't worry, I don't want babies either."

"I can't have any more babies, but I don't know if you're with anyone else."

By this time I had cut things off with Carly, so I responded honestly.

"I'm not with anyone else."

"Ok, good."

"So... can I?"

"Yes, I guess so."

Just like before, her pace was slow and methodical, her perfect body a fucking dream to play with. Every inch tight, but supple. In her matching bra and panty set, she could walk right alongside the Victoria's Secret Angels.

I held her tiny waist as she rode me, pushing her hips down onto me for maximum penetration as a licked, sucked, and nibbled her hard little nipples. I squeezed the top of her firm thighs and clamped tightly on her tight ass.

"I'm going to cum."

"Fuck yeah baby, cum for me."

"I'm cumming!"

At that point I forced myself to cum as fast as possible. I wanted her to feel me cumming deep inside of her as her body continued to quiver in orgasm. Just as the final trembles left her body, my cock exploded inside of her, flooding her with my seed. Long, strong spurts filled her as she ground against me, holding my head against her chest.

"My face hurts again."

"I can't wait until you're fully recovered."

"Me too."

She scampered away to the bathroom as I took in the sight of the most beautiful woman I've ever been with, prancing naked through my living room with two weeks worth of my pent up cum spilling from her beautiful pussy.

We texted every day on my trip and I sent her pictures and video. She got a little jealous because there was a girl on the trip I had some history with, but I tried to put her at ease. In the meantime, out of nowhere Mary (Date# 45) starts texting me a couple of days into my trip and I had to politely tell her that 'I'm seeing someone... but I'll let you know when we break up.'

I get back and we make plans to see each other a few days later. She just wants to come over and relax, so I make up a little charcuterie board and pop a bottle of wine. Her work day ran long, so she came over very late took one sip of wine and asked to see the bedroom.

Straight to business once again. She's more healed, but still needs to take it easy. Still her on top full time. As we start, she thinks we can go a little longer and I'm wanting to try new things with her.

"Do you like your pussy licked?"

"Only if you're good at it."

"I mean, I'm not professionally trained or anything..."

"You can try it, but I can't lay down."

"Well my favorite way to do it is you on top."

"Really?" she pans skeptically.

"Trust me, climb up here."

She slides her naked body up as lift her over me. Her taut little body and big hanging tits brush over me - god she's fucking hot. She hovers over my head as I stare up at her perfection. The first time I actually got a good look at her pussy and of course, it's perfect.

Completely waxed, flirty little bikini tanline, plump outer lips, a small gash revealing delicate, bright pink minora with a tiny little hood barely visible.

"Now sit down, but don't completely smother me."

"Like this?"

I devoured her completely. I licked, sucked, and nibbled her, roaming my hands all over her body, tonguing deeply into her perfection, and watching her stammer as she held tight to the headboard. She ground back and forth on my face, reaching down and palming my head, guiding me to just the right spots. For several minutes I was in heaven - it truly might be the single greatest sexual experience of my life. I've never been so turned on giving oral.

With her juices dripping through my beard and down my neck, she slides back down me, immediately sheathing my throbbing cock in her gushing hole. She came twice in pretty quick succession, then asked me to finish. I happily obliged and pumped my new trophy girlfriend full of every horny teenage kid's hopes and dreams about getting laid.

Once again, I enjoyed the post show, watching that perfect specimen sashay across the room to leak my fluid out of her body. When she returned, we cuddled up and she wanted to talk. She asked about my trip and things went sideways with her jealousy. She's convinced I'm interested in other women and my explanations didn't seem to really be helping. We went round and round, going deeper into some things we had talked about and exposed some miscommunications.

The biggest one I misread was her question about me seeing other people. She wasn't necessarily asking me to be exclusive or if I was dating, she was more concerned about my past partners and if I had been tested. Since Carly and I were both tested, and agreed to be transparent about other partners, I knew I was in the clear, but I took her question as something else. So, while it didn't stop her from taking the risk, how I answered made her question if I was being honest and it got the jealousy ball rolling.

I thought we were in the clear after we finally got to the end of that night, but I was wrong. Her texting slowed over the next week and she brushed off plans I tried to make for the following week. Finally she sent me a text to break things off, saying that she lost attraction after my trip. I didn't fight it cause frankly, I was pretty much just in it for the sex, but her rush to jealousy was a product of her own mind, not reality.

I did make one more attempt with her by sending a text and inviting her over. She kept asking why and I tried to play it off, but eventually I had to be true to my intentions and I offered a friend with benefits situation. She was NOT happy with that and chewed me a pretty good one over several texts.

Oops.

Date #64 - Nicolette the Dude

After the Liana thing blew up, I was ready for a break. We were just coming into the holiday season, I was planning a trip back home, and was just burnt out. Plus, how do you follow something like that? Every woman is going to pale in comparison physically, so take some time and do a reset.

So, like a month later, I reopen the app. Not taking it seriously, not doing long swiping sessions, ignoring matches unless they actually seem interesting - you know, the way healthy people use online dating.

Up pops Nicolette. Sassy bio, some overly filtered pictures, but cute enough and seems to have a fun curvy body. At this point, I'm being overly selective, but for some reason when I started messaging her, something clicked and it seemed like I should go out with her.

That was the last time I'm going to trust my intuition.

She beat me to the spot by a solid 15 minutes and as I approached her at the bar my "WTF Meter" pegged. She was much bigger in person and much less cute. Rocking a sweatshirt, jeans, and her motorcycle helmet next to her, she was ordering her second beer when I walked up.

We chatted, she was a total bro. Also was an active duty police officer who lived with her stepdad in a totally weird sounding situation. I felt like I was on a date with a dude. Zero interest at all. We had a couple of beers, acknowledged nothing was happening, and I walked her to her bike.

We watched a drunk couple stumble up the road, laughing and making bets which one was going to fall down first. I gave her a hug and sent her on her way. Just as she pulled away, I noticed two very attractive women on the other side of the street watching the drunk couple as they doubled back up the street.

I approached just in time for all of us to watch the drunk woman take a spill into the street and hit her head pretty good. Drunken hubby assisted, but almost fell himself. At that point, me and the two beauties, ran over to them. He was stammering about his keys and she was obviously concussed or in the least, too drunk to talk. We 9-1-1'ed them a ride and worked to keep them from wondering off.

EMT's showed up pretty quick, so we walked back to the restaurant the girls were closing down and got to talking. Try as I could, these girls were just not into me - too young, too pretty - but hey, it's still fun flirting with pretty girls.

Date #65 - Jan the Belly

Another rude nickname, but it's all I can think about. Jan was a really pretty gal, thick as all get out, and a good 5'8". She was late 30's, pale complected, almost black hair, and very, very pretty. She was also a mom to two near out of the house teenagers.

We matched and vibed quick, planning our date almost immediately. We agreed on a seafood spot right on a river in an area of town I love taking dates to and with Nicolette happening between our planning and the actual date, I almost cancelled. Arguably should have.

Jan showed up looking delicious. A little thicker than her pictures, but her giant tits squeezed into her little black tee and big round ass with thick thighs stuffed into her stone-washed jeans would make most men do a double take. Just as pretty as her pictures with pale blue eyes a light touch of freckles on her nose and a mischeviously cute smile.

Conversation was good throughout dinner and back at her car, we began to make out. She was so sexy. Kinda reminded me of a thicker, less traumatized version of Maggie (Date #30). She's a great kisser so things heated up pretty quickly. My hands found their way across her body - back, sides, hips, thighs, ass and back around.

Pretty quickly I found the skin above her jeans under her shirt, and flirted my fingers around the top of the waistband to the front.

"Nope," she pushes back.

"I'm really trying to get into your pants... I mean, I am, but I can restrain myself... just flirting with the thought of it."

"It's not that. It's just that I have had two kids."

"Ok."

"It's a lot for me to have someone touch my stomach."

"Oh, no problem."

We resume making out, my hands exploring under the clothes even more and more as we play. Up the back of her shirt, I flick open her bra, then shove my hand down into her boy shorts, pawing wildly at her perfectly fleshy rear end.

"I can't believe you just undid my bra!" she scoffs with a giggle.

I smile, pulling her ass to me and pressing my hardness to her stomach.

"You're sexy."

"You're sexy!"

We continue and once again, I tease the waistband, popping open the top of her pants before retreating again to her ass, sliding my exploring hand around her thigh and between her legs, my other hand wrapped around the back of her neck and pulling her into our kiss. The side of my hand begins rubbing gently against her dampened panties and she writhes into me.

"Mmmmm uuuugghhh"

She gently grabs my forearm and pulls it up, my hand now finding her belly and under her shirt to her massive tits.

"Ok, we have to stop."

"Yeah, it's a lot."

"It takes me a long time to get this comfortable usually and I feel really exposed."

"Well, we are in a parking lot. A dimly lit parking lot with nobody around, but still."

"No, not like that. It's just... I've had two kids."

I realized in that moment that the situation wasn't the problem, it was her self-consciousness about her stomach.

"Hey, no problem. Here..."

I rebutton her pants and adjust her shirt back down.

"I'm sorry."

"For what? This is first date and probably not a bad idea to chill a bit anyway."

"Yeah... so... you're really sexual, huh?"

"It's a thing for sure."

"I like that. Seems like we're compatible like that. What's your favorite position?"

"Cowgirl for sure... not cause I'm lazy, just cause it gives me full access. And cause I'm lazy."

"Oh, it's doggie for me."

"I'm down with the dog. Also like prone bone and truthfully, upright missionary is vastly underrated."

"Upright missionary?"

"Yeah, like missionary, but I'm not laying on top, we're more like an 'L' so I can look at you."

"Oh... so cowgirl and the 'L' thing... it's going to take a lot for me to get there."

"What do you mean?"

"I've had two kids... so..."

"Ah, no worries."

Except, worries. I don't know what she looked like cause we weren't there yet, but I can't deal with self-consciousness in the bedroom. It ruins it. Lovely Lisa (Date #9) had the same problem with cowgirl, despite not having kids or much of a belly.

Yep, that was it. We chatted a bit more, parted ways, and the next day I texted her wishing her luck and explaining that something was missing for me.

Date# 66 - Mary the Speedy

This isn't sexy, but it was kind of fun, so I figured I'd include it. Despite me blowing off Mary during my camping trip, she never stopped texting me. She waited a couple of weeks, but circled back around again unprompted just as things were falling apart with Liana.

I kept it PG until Liana gave me the boot and then resumed flirting hard like old times. She wasn't having any of my friend with benefits nonsense, but I did enjoy chatting and playing around with her. At one point she mentioned running a singles event, inviting me, and that prompted a discussion about alternative dating options - matchmaking services, singles events, and speed dating.

Mary had done speed dating in the past with poor results. I thought it sounded lame until she mentioned that the events are almost always dominated by women, "and they're all hot and the guys are NOT." Not that I trusted her judgment in hot women, but at least the ratios were promising.

I poked around and found an event a few weeks off and invited her to join me. She teased that it'd be weird given our bit of history (and the fact that she's super into me, but would never admit it) and I just told her that no matter what, at least we'll have someone to make out with at the end.

I picked her up at her place and we drove downtown to a spot I was familiar. It just happened to be the hotel where everyone stayed after my friend's wedding. We all piled in the bar a couple of times that weekend so I had it pegged.

I immediately noticed the lack of competition. Two really hot women, a few attractive gals, and only a couple total no-gos, but it might as well have just been me and just one other guy. I mean, there were a few other guys, but in no way were they competition.

Despite Mary trying to cock block me right off the bat with the pretty Russian blond at the bar, it went pretty well. Russian blond was a terrible flirt and had that Eastern European - can't figure her out - thing going on. Then it was on to a reasonably attractive woman from Colombia who I could barely understand and was angling for a husband, fast.

Up next a nerdy redhead who was very cute, but also loved Jesus I think cause my brashness and cursing was definitely putting her off, though she was sweet as can be. From there it was on to the world traveler nerd girl who wasn't horrible to look at, appeared to have a nice curvy body, and was practically screaming "fuck me right here Jack" with her eyes as we talked. Had I been in a little of a different spot, I would have certainly taken her up on that.

Then came the slender blond, the only one who wasn't 6-8 years younger than me. I spotted her right when I walked in, pegging her for the most attractive. I started talking to her and she was clearly, not the most attractive. Nice enough and would be a solid bar pull, but her vibe was weird. Rosie Perez's crazy hot sister was around the next corner - a total surprise.

I actually remember her name because she was so fucking hot. Mid-30's Puerto Rican from the Bronx, hourglass figure, lips, hips, and tits for days. Angel was BEAUTIFUL (despite the tough accent). We had a pretty good chat and the flirt game was decent - she was the only one I really wanted to pull that night.

Finally came the Nubian princess. From somewhere in Africa, this girl was a goddess. Skin as black as night, a figure that just didn't quit, and a face that belonged on magazine covers. She was also the youngest there and immediately started talking marriage and children like she was reviewing CV's for life partners.

By the end of it, Mary and I were chatting with random hotel patrons at the bar while our bartender when to "shoot my shot" at Angel. We chatted with the Russian blond a bit too, but ultimately called it a night. I took Mary home and we made out a bit in her driveway. This apparently confused her as "all night we were just buddies, but now you want to make out."

Yeah, that was kinda the deal from the start.

Not sure I'd ever speed date again, but it was a good experience. I got on the app after and 'yes'ed everyone, with the unreadable Russian, the polite and Holy redhead, and smokeshow Angelisa being the only ones not to like me back. I was in breather mode, so did nothing with it.

However, after that experience, I have considered hosting one of the events. Our host sucked, but it seemed like a fun gig to do every now and then. Plus she told me I'd get paid $75/hr to interact with single women. Since there were generally more women than men, the host routinely talks with them as they wait for the signal to switch "dates." Seems like fish in a barrel.

Date# 67 - Jessica the Nightmare

God damn camera phones and their ability to fool us. Jessica was cute in her pics though seemed a little hesitant to smile - sometimes that means crooked teeth, sometimes that means dental disaster. However, in one pic she had enough of a smile to appear as if we were just talking crooked teeth, which I happen to actually like. Plus, she was a lean and busty redhead with freckles, so what's not to like?

All of it.

We met up at the same spot I first took Clara, which was a surprise because I honestly thought I'd never been there before when I set it up. Of course, as I approached, I recognized it immediately. The only reason I recognized her was she happened to be the lone woman standing by the entrance alone and the closer I got, the worse everything came into focus.

Her body was the kind of frumpy instantly recognizable as being built by massive weight loss. No shape, loose skin on the back of her arms, and her face was almost sunken and gaunt. I believe the term now is Ozempic face. Despite her efforts to hide it when she greeted me, her smile was definitely more dental disaster than crooked teeth, though she had that too. Dead teeth, others generally discolored, and something a bit off about her bite too, like her jaw was twisted.

Harsh, I know, but look people... this is online dating. Dating. You're going to meet. Be honest with your pictures. Don't set yourself, and others, up to fail.

We sat for drinks and I pumped the brakes straight away.

"Before we think of ordering food, let's chat for a bit and see if we have more a vibe cause you can't tell anything through text."

She agreed and the conversation was labored. She knew only one of us were well represented by our pictures and I could tell she was uncomfortable. After the first round, there was a solid lull she couldn't fill and I didn't want to, so when the server approached again, I looked at her and shook my head. She nodded, and I asked for the check.

I gave her a hug, wished her luck, and said, "fuck online dating" once again.

Date # 68 - Reyna the Revelation

With that nightmare fresh on my mind, I returned home to spend the holidays with my family. Shortly after I left, my father who had been ill, passed away. Dating was the furthest thing from my mind and I had no desire to do anything social at all.

I didn't let that last too long. While still struggling with my grief, I emerged from my cocoon, more moth than butterfly, and forced myself to be social. I found a dive bar near my house and quickly became a regular. I was just focused on my social life in general, steering away from any sort of dating, but significantly increasing my real world interactions. The thought of another Jessica situation made the idea of another swipe mystery prize (or punishment) seem completely not worth it.

Over the next couple of months I was on the prowl though. I flirted with women everywhere I went. Most everything went nowhere, but instead of go nowhere matches, I was having go nowhere text exchanges with women I actually knew I was attracted to. There were a variety of parking lot make outs and a date here and there, but nothing too interesting. My new angle of attack yielded much fewer interactions and "results", but was much more satisfying.

I'd been getting pretty good at meeting women in the wild when Reyna entered the picture. Out with coworker at a new dive he wanted to check out, I stumbled upon Reyna while I was waiting for a beer at the bar. The guy next to me stepped away and there she was, dumping years of trauma on her friend a few stools down.

She was cute, just over 5' tall, long thick dark brown hair, a nice little curvy body, and LOUD. Stereotypical Italian MILF on the verge of hitting the wall.

I eaves dropped while waiting for my beer long enough to determine she was in the middle of a break up that was long over due. About the 2nd sip of my fresh beer and her friend gifted me the perfect opener.

"You just need to get out there and have a good time!"

"Excuse me, sorry to interrupt. I'm a good time, what's your name?"

They both completely lost it, Lisa laughing and play slapping Reyna, almost shoving her into me and Reyna with her face buried in her hands cackling uncontrollably. We chatted briefly about the fresh separation and future divorce before Lisa excused herself to the restroom. By the time she returned, Reyna and I were in a full on flirt, her resting her hand on my shoulder and me with my hand on her thigh tickling the skin just below her hiked up dress.

Within 10 minutes, Lisa pulled her aside at the corner of the bar and after a bit of back and forth, she left and Reyna came back, hanging herself off my shoulder and giving me "let's get out of here" vibes.

"You want to go make out in the parking lot, don't you?" I joke.

"OH MY GOD! No, I don't want to make out in some bar parking lot."

"That's a shame... cause I'm pretty good at it."

"Bar parking lots or making out?"

"Both."

I turned back to my buddy, who was gazing off at the TV behind the bar.

"This girl's trying to take me home... you good?"

"I am NOT trying to take you home!"

"All good man, you guys have fun."

"C'mon, let's go..."

I grabbed her hand and lead her out into the parking lot, spinning her around and licking her neck just after stepping off the curb.

"I'm not doing this here."

"Where are you doing this?"

"Oh my god, this is so bad..."

"Seems like you could use a little bad... how long has it been?"

"Fucking forever, but not here... it's too public."

"Easy girl, we're just making out. I'm not trying to fuck you in the parking lot."

"Still, I need..."

We were interrupted by a couple of guys stumbling out the door and turning the corner for a smoke.

"I need a little privacy. Like, is there a park or something around here? Some swings?"

"Making out on the swings? Boy, it's been that long, huh?"

She's on her phone scrolling.

"Here, let's grab a six pack and just go talk" she offers, not even looking up at me.

"I guess I'll follow you."

And off we were. I followed her to a gas station a few blocks away and then onto a secluded park a little ways further. We parked alongside the road, she grabbed the six pack from her back seat and a little blanket from her trunk.

"Park's closed."

"What?"

"Look, there's a fence and a sign saying it's closed for construction."

"Is that a bench on the tennis court?"

"That part's open."

We cracked a couple of beers and walked into the middle of the tennis courts, plopping down on a cold aluminum bench. She wrapped her miniature blanket around us and we began kissing.

A good enough kisser, she was immediately turned on and raking her fingernails up and down my arms, breathing heavily, and quickly mounting me knocking my beer and breaking it onto the pavement.

"Oh fuck."

"Don't worry about it."

"I don't care about that... it's this. This is crazy."

"A little, but it's fun ain't it?"

She looks down at me as I pull at the flesh from her sides, running my hands up her ribs and pulling her back to me.

"Mmhmm"

We kiss. She's grinding me feverishly as I paw at her ass, her skirt hiking itself up until my hands are fully clasping her cold, soft ass. I push her back and begin to readjust my cock inside my shorts. She stands, pulls her skirt down and turns away.

"Where are you going?"

"This is crazy."

"A little."

She turns back around.

"I want to fuck you."

"We can arrange that."

"This is crazy."

I pull the wadded up blanket from the bench and lay it on the ground in front of her, sit down and reach for her hand.

"Are you feeling crazy?"

Without a word she steps over me and sits on my stomach, pulling my hands to her tits and arching her head back, her long brown wavy hair tickling my knees. She lurches forward, grabbing my face and jamming her tongue down my throat, immediately grinding powerfully and getting me rock hard.

"Mmmm" she pants into my mouth.

I run my hands up her thighs, pushing her skirt up past her ass, using her motion to make exposing her effortless. She bites my lip and sits back, tugging at my belt and tearing open my shorts, shoving her hands into my underwear and pulling me out into the crisp evening air.

She stands up, bents over and places my meat onto her tongue. She sucks as she pulls her thong down, releasing me, and kicking her underwear off one foot. Sitting back down, she rubs her glistening muff up and down my shaft, then reaches up her back to unzip her black dress. Pushing forward, she drops the front down to expose two solid handfuls with cute nips and a bit of hang.

Gripping them hard I begin to buck into her, teasing my cock closer and closer to slipping in. She leans forward over me and as I take a nipple into my mouth, she reaches between us and strokes me roughly. Releasing her nipple with a satisfying pop and graze of the teeth, I lift my hips and she sits back, directing me inside of her.

She shudders as she lowers herself over it, her gushing hole stretching from years of being ignored.

"MMMMMMmmmm!"

She grinds me deep inside of her, shaking as she bears down and my girth fills her. I feel her juices pouring around me as she raises up. The cool breeze highlights the wetness between us with a momentary chill before she drops back down and grinds me further.

"I want to feel you cum."

I grip her hips and rock her back and forth, pushing my myself up and down, faster and faster, until shes merely hovering over me and I'm splashing into her furiously, her little tits spinning just below my chin.

"Oh fuck! That's it! That's it! Please cum!"

"ARRRGGGGHHHH!!!"

In just a few minutes I built up and uncorked the load of a lifetime. I felt every pulse spurt more and more of my fluid deep inside of her. She clamped herself to me, biting my lip and quivering as she ground every last drop out of my nethers.

"Oh my god, I needed that."

"I think I did too."

We quickly pulled ourselves together and walked to our cars. We exchanged numbers, kissed, and parted ways. Later that night, she texted me, but I didn't respond.

I had a moment with myself on the 20 minute drive home that night. I couldn't believe I was so reckless. Within an hour I met and fucked some random woman. At first it felt like an accomplishment, but then it felt gross. Unprotected sex in a fucking tennis court at 10 o'clock at night with a complete stranger who didn't ask any questions before demanding I pump her full of cum. That's college shit, not the behavior of a man in his 40's. Definitely a wake up call.

Time to grow up.

At least with online dating the illusion of knowing someone is possible, but in reality, this wasn't the first time I'd done this. Chat with someone a few days, go out on a date or two, then just start fucking without a care in the world. It WAS crazy. Stupid. That's not to say I didn't protect myself most of the time or at least ask questions. And I guess I was getting tested regularly anyway, but still, I felt like I needed to slow my roll a bit.

Over the next couple of days I really thought about the situation. I had already slowed down on dating considerably, but I decided to make a concerted effort to control myself. No more one night stands, no taking big risks in general. Try to do it the old fashion way, which meant no more online dating. It's too easy, too tempting. I didn't need it to meet women anyway, but with it, I had the potential to meet an unlimited amount of women very quickly. At least in the real world, options were more limited. So, that's where my focus turned.

Date# 69 - Agnes the Vulnerable

I'm not particularly proud of myself for this as I have a visceral disdain for cheating. Cheaters are right up there with thieves as far as scum of the earth care concerned. Then again, I have an admittedly strong scumbag streak that runs through me so assisting a cheater... I'm not beating myself up about it.

After a lakeside party for my buddy's birthday, the host had passed out and we ended up at the infamous karaoke bar. Place was packed and I made a few rounds chatting people up until I ran into a group of four hot late 30's women. Using the one girl who was passed out as my opener, I chatted up the other three, targeting Mary who stroked my beard and rubbed the back of my freshly buzzed head as we flirted.

Then I noticed her ring. She was married. Surveying the group, they all had impressive rocks on the worst finger. Fuck. Been here before.

Women go out on a girls night looking to get the male attention their husbands have been neglecting. Largely, they're a waste of time, but a surprising amount of them are pretty quick to jump into the back of their grocery getter to cheat on their unsuspecting husbands. Years on the prowl and many, many offers such as this have ruined my faith in humanity. I wonder if these slags feel anything as they drunkenly scramble to scrub sex fluids and reinstall car seats in the driveway before climbing in bed with their loyal 'till death do us part'ners.

But, I was drunk, and Mary was tall, thin, blond, and beautiful with big green eyes and bright red lipstick, so I didn't concern myself with humanity too much.

I buzzed between groups, touching base with my friends, running into a guy I used to train jiu jitsu with that I randomly, but consistently, run into every 2-3 years, and ended up doing some shots with the four married women.

Mary had her fill of my attention at that point and Agnes was getting chatty. Eastern European, but raised in the states, she was a natural beauty with sandy blond hair, average height, high cheekbones, very little makeup, and some nice curves sneaking through her red flowery maxi dress. The flirt was strong and I was calling out her group for being married and on the prowl.

"We are NOT on the prowl... just having some fun."

"Husband approved flirting?"

"A little flirting never hurt anyone."

"As long as it's just flirting."

"It is... not that he'd care."

"Oh, so tell me you're a couple of freaks without telling me you're a couple of freaks."

She laughs, "No, it just probably wouldn't even notice."

"Oh damn, it's like that?"

"Yeah, it's like that."

Then we got deep into it. They married young, basically hated each other, but were sticking it out for the children. Lived completely separate lives, separate beds, and no sex for almost 3 years.

Having a little shred of humanity left in me, I went into counselor mode and gave her the best advice I could. I've seen this sort of thing before with friends and I have a good idea of what works and what doesn't, though once something is that far gone, I doubt there's any fixing it. Once someone quits on their vows, it's done.

Getting to that point and justifying in my head that making this gal squirt in the back of her mini-van wasn't really going to do any harm in the world, I turned on the charm and started flirting again pretty heavily.

My friends left and while still in flirt mode, my karaoke song was called and I was up to perform. I ended up with four backup dancers and Agnes was getting a little handsy as they took turns grinding on me. I made my move just after we stepped off the stage.

"Probably time to go outside and make out."

"Oh really? Seems more like it's time for me to walk away from this conversation."

"And go outside?"

"Nice try."

"Barely trying."

"I can't make out with you, I'm married."

"Sorta." I grin.

"Technically." She laughs.

"What happens in the mini-van, stays in the mini-van."

"You drive a mini-van?"

"No, nevermind."

We went back and forth a few more times, but it was going nowhere. I excused myself and found the bachelorette party I had talked to earlier, making no headway there either. I made another friend at the bar, had a couple more drinks, and closed out my tab. It was last call, so I hit the can and on my way out, noticed the married gals heading toward the door.

I got jammed up briefly with some fat girls I had talked to earlier, but made it outside just in time to see Mary and Agnes hugging before Mary stepped into a Lexus SUV. Agnes turned and walked towards me, fiddling with her purse in search of her keys.

"Want to see my van?"

"You really don't have a van, do you?"

"Maybe."

"I hope not, that would be creepy."

"Creepy because of the bed and mirror ceiling, or creepy cause of comfortable ergonomics and reasonable gas mileage?"

"You totally are the type of guy with a bed in your van."

"I do have a bed, but not a van."

"That's nice for you, I have a bed too. Time for me to go."

"I was talking about my truck."

"There's a bed in your truck? Why?"

"All trucks have beds, that's what makes them trucks. You know, the back where you put all your shit when you move or something."

"Oh... ok... I'm leaving."

"You keep saying that, but you never actually walk away."

"How about this?"

She pats my chest and pushes by me.

"Ok, have a good night. Drive safe."

"You're going to let me walk through this scary parking lot alone? Didn't you say you were a gentleman?"

"If you're trying to seduce me, it's working."

"Ugh, don't ruin it..."

She turns and continues walking. I catch up and begin guiding her through between cars with my hand on the small of her back.

"Thanks for the chivalry."

"Thanks for making out with me."

"We haven't made out..."

"... yet." I smile, stepping in close and wrapping my hand around her back, pulling her towards me. She stares up into my eyes nervously, placing both hands on my chest almost as if she wanted to push me away. I slowly lean in, softly kissing her.

"Ok... that was... that was nice, but I have to go..."

"Ok."

I stand firm, not moving. My hands on her hips, fingers lightly caressing her sides, cock beginning to stir between us. She isn't moving either.

I lean in, stopping at the last second, feeling her gasp just before our mouths connect. Another soft kiss. A light brushing of my probing tongue. My hand runs up her back and pulls her in tightly as I fully kiss her. Her arms wrap around my neck as her tongue swirls into my mouth, dancing perfectly with mine. Agnes is a phenomenal kisser.

"Fuck."

"In my van?"

She laughs, "stop. I can't. God I want to. Fuck I want to... I can't. I just..."

"It's ok, I'm kidding. Just a little makeout sesh, no biggie."

"I have to go."

"Ok."

I stand firmly, my hands returning to her waist and her hands still clasped behind my neck.

"I'm leaving now."

"Yeah, you should go."

Neither of us move.

"Maybe just one more" she smiles.

"Another for the road is always a good plan."

We made out for a solid 15 minutes. I never pushed it past first base and once we started grinding against each other and my hands were fully roaming her soft round ass, glancing up to her ample chest, her "I have to go" actually became serious and I opened her door, gave her a little peck, and we parted ways.

Date# 70 - Jess the Cruiser

We'll go ahead and file Jess under, "missed opportunities cause I'm a fucking idiot." I'll be kicking myself about this one for a long time.

I hadn't been on a real vacation in years, so when an opportunity arose to go on a cruise, I jumped on it. 5 days of fun in the sun and 5 nights making myself well known to my fellow cruisers. The karaoke helped for sure, but by halfway through the trip, I was a household (cabinhold?) name because of my late night antics at the club. The entire trip people would approach me by name and I had to scramble to see if I could remember who they were. It was a blast, though pretty exhausting.

I had some success in flirting and some grinding dances each night, but never really had an opportunity for more until the final night.

I noticed Jess a few days into the cruise at one of the bars onboard. She was a hot little thick blond, young and drunk; seemed a little wild. She was part of a bigger group, obviously family, that I casually infiltrated the night before our interaction. Through that recon, I figured she was totally off limits as giant intimidating brother and giant intimidating uncle were in tow every time I saw her.

That last night I found myself at the bar, listening to some house band cover semi-obscure hits. I made my rounds, chatting up the college crew I had been partying with most nights, the couple from Kentucky who were my age and just great, salt of the earth people, the single mom around my age who I met on an excursion that was attractive and fit, the young couple with gold teeth who yelled my name across the buffet every morning, and a few others - it was a busy night.

Consistently, Jess was the only one on the dance floor.

She was lost in her own little world as she danced and spun around the empty floor, striking long mascara clumped lashes pinned to her sun-kissed cheeks, messy bleach blond hair flowing in the air and over her shoulders as she raised her arms to the ceiling and twisted her hips while dropping into a crouch and popping back up. Her white flowery sun dress hugged her waist, barely highlighted her perky handfuls, and showed a hint of thigh above her knees while guaranteeing a nice round ass was hiding underneath. She looked every bit sexy southern belle and dangerously tempting farmer's daughter in one hot little drunken package.

With her cornfed pro-wrestler sized family patriarchs watching from the sidelines, I knew I couldn't just make a beeline for her, but I had to make something happen. It was my last night, so why the hell not. I opted to grab a new drink and wander the perimeter, this time using my Rolodex of contacts to give me an excuse to interact with her naturally. I worked the outskirts, grabbing everyone I knew, and anyone else unlucky enough to make eye contact, onto the dance floor.

Next thing you know, the dance floor is full and she's taken notice.

"You did all this."

"I know, it's one of my skills."

"Impressive. What other skills do you have?"

"I'm a great dancer."

"No you're not."

"You haven't seen all my moves yet."

"I've seen enough."

"What about this?"

I spun around, bent over, and did my best (very poor) twerk, then dropped low and bounced back up, sticking my hip out and slapping my ass.

"You should never do that again."

"I know, it's too hot... dangerous."

"It's something." she laughs.

The song ends and the band starts yapping as they did between songs, clearing the dance floor. I resume a previous chat with Kat, the single mom from the shore excursion, pulled her to the dance floor as a slow number played, and watched as most of Jess's family disbursed. Seeing an opportunity after excusing myself from Kat, I decided to see what the situation was with the remaining family, noting that fee fi fo fum uncle was gone and only her gargantuan brother remained. Since he was the one I talked to most during that prior interaction, I figured this was my best play.

We chatted briefly and were interrupted by his wife. Once again noticing Jess as looking pretty lonely on the dance floor, I tried to lure the couple out there as a ruse to get myself out there again. Next thing I knew I was out there among a mob because "Save a Horse, Ride a Cowboy" is a popular dance number these days apparently. I took the opportunity to flirt with her a bit, nothing too overt, just told her she needed to calm down on the hair flipping and some of her more suggestive moves. She responded by qualifying herself and telling me how she just graduated from college and landed a great job (that for the life of me I cannot remember) along with an impressive side gig (no surprise I cannot remember that either). That was exactly the vibe I was looking for - once they start trying to impress you, you know you're in.

A few more songs and I wasn't paying attention, almost missing that she was leaving with her crew. Luckily I caught it just before they bailed, so I made my way past them to talk to some other people, staking a position in their path as to intercept them on the way out. It worked perfectly and I caught the group just as they exited.

"You guys aren't leaving yet, are you?"

"Yeah, it's getting late and we have to pack." Jason, the big brother, lamented.

"I'm not going." Jess mumbled.

"You're going." Jason's wife quipped.

"I'm going to the casino." Jess retorted.

"You're going to bed." she argued.

"She can take care of herself," Jason pleaded, pulling his wife away.

Sensing my presence may have been part of the problem, "Well, you guys have a great night, nice to have met you." I retreated back into the bar, turning back just in time to see the group part ways, with Jess alone walking towards the casino.

Doubling back, I caught up with her just as she made it to the casino bar.

"I'm out of drinks."

"And you haven't had enough?"

"No, I have. I think I'm going to bed."

"You don't want to go to the club? For such a little dancer, I'm surprised I haven't seen you there yet."

"I've seen you there."

"Uh oh." I laugh.

"Yeah, you should be afraid."

"The only thing I fear is that hair flip."

She giggles.

"I'm drunk, I should go to bed."

"Ok, you sure you can make it."

"I'm not that drunk."

"Fair enough. It was nice meeting you."

"It was fun dancing with you."

And, she was gone. I grabbed another beer, chatted with some old guy I met the night before, and made my way to the club. It was just starting to pop and I made my way around, talking to the groups I had met before and chatting up a few others. Maybe an hour later, the place was packed and I was at the bar, taking a break to cool off and getting a fresh water when I felt a little scratching tickle on my lower back.

Jess.

Gone was the flowy sun dress and in place was a tight red shirt with frilly straps and matching booty shorts. A hot little PJ outfit, advertising every perfect curve of her young, semi-chubby body. This girl was hotter than the sun.

"Holy shit Jess, you're still alive!"

"I came back to dance."

"Well, let's go!"

I grabbed her hand and led her towards the dance floor. Just as we were about to hit the densely packed crowd, I tug on my wrist from the side had me locked in with Mike, the guy in the wheelchair with long dread locks that I chatted with every time I saw him.

This is where I completely fucked up.

"Hey, let me say hi to this guy real quick and I'll meet you out there."

"Ok."

And that was the last time I saw Jess. I spoke with Mike for maybe 5 seconds and lost that beautiful girl in the sea of chaos on the cruise ship dance floor. I scoured the place for a solid 20 minutes before running into the college boys and asking if they had seen her.

"Yeah man, she left a while ago when we were coming in... said she was going to bed."

Based on the timeline, if I had to make a bet, I'd say she didn't make it through the song that was playing when we were walking out. I bailed on her long enough for her to say "fuck it" and end the night. She was there to see me and make bad decisions. I totally blew it. Smooth move Jack, smooth fucking move.

Epilogue

My original goal was to run the first 50 in this series as a play on that goofy movie, but I never actually found the end of the maze and just kept writing over the last 18 months. We're now caught up and I feel like my exploits are beginning to become dry and boring. It's all the same thing. Meet girl, flirt with girl, get frisky with girl, maybe fuck girl for a while, repeat - sometimes with a weird, funny, or embarrassing story sprinkled in along the way.

Now that I'm done with online dating, the weird, funny, and embarrassing stuff will certainly slow down, but I'm courting younger, more attractive women at a much higher ratio. So if you're in it for the fun stories more than the sex, it's probably not going to get better for you. Then again, this is Literotica, so you're probably more interested in the down and dirty anyway.

Here's a few from the bar that could end up as segments in the coming weeks/months:

Lacey - 23, 5'10", blond, blue eyes, lean with wide hips and a nice heart shaped ass

Kristen - 25, auburn hair, hazel eyes, freckles, braces, smokin hot little body like Annie (Date# 49)

Karla - 27, tall, brown hair and eyes, thick top to bottom, former D1 athlete, sassy

Patty - 27, 5'9", dyed red hair, hazel eyes, thicker than a Snickers (just short of disaster)

I guess I'll leave it up to you. Are you as burnt out by my exploits as I am? Should I pursue these options at the bar? Maybe I should just dust off some of the old friends with benefits and set up a rotation. Or is it best for the world if I renounce my ways, find religion, and take a vow of celibacy?

Comment and let me know if anyone's still interested in me continuing this series until I fuck up and get married or my dick falls off.

~Jack