The 50-First Dates Ch. 51-60

The last several years have been a blur of sex and indulgence. I've honed my craft and maybe, just maybe, not exactly used my power for good. Ok, definitely. I've done a lot wrong, but most of all, wasted my own time. Let's be honest about my situation. I am feral. By this point I am at the intersection of desirability, skill, and ambition. Ethics and morals are loose, if not merely situational. I still maintain honesty, but I've began doing things that I really can't be proud of.

When we last left off, I had a new girlfriend. Well, kinda. I had one that was fun enough for me to temporarily commit to. Fun-sized Annie was a lot of fun for about a month before she got fed up with my lack of depth with her. Truth is, this was an ongoing theme. I am great at building attraction, but not so good at building relationships. I keep things far too superficial and don't really allow myself to open up, nor do I put much effort into really getting to know these women. I'm destined to be great for a fun time, but never for a long time.

Now, that girlfriend thing, she's date #51.

Date #51 - Kinsley the Cool

Another swipe I was taking a chance on. Kinsley had a cute face, bigtime cleavage, and no full body pics. Profile seemed fun so I swiped and immediately the conversation was top notch. Instant vibes and quick to go on a date. She recommended a gourmet burger spot close to halfway between us and we went from match to dinner in just a couple of days.

She arrived right on time and surprised me by being way more attractive than her pictures. Mid-30's, 5'8", nice tan, blond highlights, a little shimmer on her prominent cheekbones, and a thick curvaceous body. Her massive tits swayed side to side under her sequined halter top and plump ass popped with each step under her tight jean skirt. She was all sorts of the right kind of sexy.

Pretty standard first date dinner, but the conversation was stellar. That quick vibe continued to escalate as we talked dating horror stories and shared some laughs. Past all the getting to know you stuff and long discussion about how gifting someone anal plugs is not appropriate after a few dates and before you slept with them; Kinsley was just fucking cool. Another one where we were just totally on the same page with everything immediately.

We joked and teased through our meal and while we had discussed just doing dinner and making it an early night, the attraction was so strong I lobbied to continue the date and she happily agreed. We tossed around a few ideas and I brought up karaoke. By this time my hand was already casually caressing her thick silky thigh and she was petting my arm consistently.

Walking to our cars, I pulled her in for a kiss as we crossed the parking lot, catching her off guard.

"I was not expecting that!"

"What were you expecting?"

"I don't know, but I figured maybe at the end of the night."

"I'm sure we can think of much worse things to get into by the end of the night" I said, slyly smiling.

"Oh, like dive bar karaoke?"

"Something like that."

Another quick little kiss and we jumped in our cars, me taking the lead with Google Maps navigating us to the nearest karaoke spot. We pulled up and both wondered if we were at the right place. It looked like a radio station with no obvious bar, but up some questionable fire escape style stairs was a door with a neon "Karaoke" sign above it. Against our better interests we went inside.

What a strange place. Like a scifi film. A long hallway of black plastic reflective panels and LED string lights lining the ceiling, weaved around with doorways to random vinyl covered lounges spread about. The first couple of rooms were lit up and empty, but we eventually found one with a crew of rambunctious teens. This wasn't a karaoke bar, it was a private karaoke lounge.

We had a little laugh acknowledging this is not what we were in for and began to find our way out. Through the labyrinth I noticed a darkened lounge with the door cracked.

"Check this out."

"What are you doing?"

"This..."

Grabbing Kinsley's hand I pulled her into the room, pressed her against the wall and kissed her hard. She ran her hands down my chest as I felt down her body, running my fingers slightly up the side of her skirt as she lifted her knee around me.

"Stop, we're going to get caught!"

"By who? There's nobody here."

"Somebody has to be here."

"I'm not so sure..."

The words hadn't fully left my lips when the light flipped on and a stocky little Asian guy who looked half Comicon, half Yakuza quipped, "you two with a group?"

I didn't bother with any explanation, just said we were at the wrong place and he walked us to the door. Back in the parking lot we laughed about how weird the whole thing was and I pulled up directions to the karaoke dive Hannah (Date # 41) introduced me to.

We had a blast singing, doing shots, and flirting. I found out later she took a video of me and sent it to her her friends. I think that gave her permission to escalate things - I'm sure the tequila shots helped too. After a little kissing, I licked up her neck, grazed my teeth over her earlobe, flicked it with my tongue and gave it a little suck causing goosebumps to rise up her body.

"I want to show you what you do to me."

She pulled herself forward, grabbed my hand and slid it the rest of the way up her skirt giving me seductive eyes and a little smile. Spreading her legs open, my fingers met with a wetness pouring through her silk panties. I teased gently with my fingertips.

"I think it's time to get out of here."

"It's definitely time to get out of here, but I want you to make sure I get home safe."

"I see you Kinsley, I'll be happy to escort you home."

At her place she wasted no time, leading me up the stairs and into her massive bedroom. Sloppy lips, swirling tongues, and gnashing teeth left a trail of clothes from the threshold to mattress. Falling in together, our bodies tangled and we rolled around. My hard cock felt her gushing heat pour over me as I effortlessly slipped inside and she found her way on top.

We fit together extremely well, like our loins just knew what to do and the rest of our body's were merely along for the ride. Raising up she rocked her hips back and forth as I marveled at her body. Bust was definitely aftermarket, but incredibly well done. No visible scars, very natural hang and feel despite being cantaloupe sized. She had great bikini tan lines and cute little nipples with half dollar areolas. She held my hands as I squeezed her tits together, massaging them in rhythm with her grinding. Her head rolled back as I released her chest and rubbed down her belly to her thighs - just the right amount of thickness, everywhere.

She leaned forward and kissed me, rising up and bouncing with a satisfying wet slapping sound. I reached back and gripped her round ass, pressing my feet into the bed and thrusted in time with her strokes, plunging completely into her depths and nearly falling out with every cycle.

"Oh god this is good."

"You're pure fucking sex."

"I want to cum."

"You're allowed."

She stops, rolls to my side, reaches into her nightstand and pulls out a small pink vibrator.

"Does this bother you?"

"Only if you tell me it's going in my ass."

She laughed, "no it's for me. The only way I can get off."

"As long as you get off."

She smiled, twisted it on, and laid back with her legs spread wide gently rubbing it up and down her little tan outlined racing stripe.

"Now fuck me and make me cum."

"Maam yes maam" I say, jokingly throwing up a salute.

I climb on top as shes writhing beneath me, her massive breasts pushed together and knees splayed to the sides. I grip the back of her thighs, pushing them up and allowing my granite member to press against her vibrating womanhood. Dipping my hips slightly, I push in, feeling her tighten around as my thickness penetrates deep.

"Oh FUCK!" she quivers, her orgasm shooting through her about halfway through my third slow thrust.

"Oh fuck yes!" she pants as it extends through several more slow, deep strokes.

"Now it's your turn. Fuck me hard and cum inside of me."

Never saying no to a good time, I ground my hips in deep, sliding my knees forward and sliding my hands to her chest, forcefully pushing her into the comforter. She struggled to maintain control of the vibrator while I pounded hard against her, banging the headboard against the wall as she moaned and panted, "fuck yes... fuck yes... fuck yes... fuck yes..."

I clamped hard onto her tits and buried myself against her cervix, exploding like a supernova with long spurts we could both feel painting her womb. She reached up and grabbed my face, spreading the smell of sex into my beard as I collapsed on top of her and breathlessly kissed me deep and slow.

"I'd say this was a good first date."

"Uh, yeah" she laughed.

Our second date was much less formal. We originally had plans to grab oysters at a spot near her place, but she had to work late so I just met her at her place when she got off. We shared some wine, ate a couple of gummies, and cuddled on the couch when she brought up mushrooms.

Apparently the last guy she dated, who gave her three sizes of butt plugs on their third date, had given her mushrooms, but she broke it off with him before they could do them. It had been a while and neither of us had to work the next day, so we indulged.

"We should have sex on these."

"Nope, bad idea. Lots of drugs pair well with sex, shrooms aren't one of them."

"Really? I thought it would be cool."

"It's definitely not."

"Then I guess we should have sex before we start feeling them."

"My thoughts exactly, now strip for me."

"Do what now?" she laughs.

"You have a sexy body and I want to look at it."

She giggles, "I've never stripped for anyone before."

"Just move slow and be sexy."

She held her chin, her mouth agape, with a french tip tapping a couple of times on her front tooth.

"I need more wine."

She chuckles as she moved from the couch and sauntered into the kitchen. Pouring a glass, she slowly sticks her ass out a bit and sways back and forth, building the courage to put on a show. She glances back at me watching her, giggles and shakes her head, then scrolls her phone. Just as I'm beginning to think she's blowing off my request, a slow Beyonce song starts playing and she turns around, face beet red.

A big swig finishes off her new glass and she slowly walks forward, swinging her hips and slowly lifting her tank top to expose her stomach. She spins around just as she's almost at arms length, bends forward at the hips, then drops her ass down in time with the music, giving it a couple of bounces before rising back up.

Turning back around, the grin that was previously welded onto her face, melted off as a serious seduction swept over her and she stepped between my legs, leaning forward for a kiss, only to shove me back into the couch just as our lips met. Turning her hips side to side, she lifts her shirt enough to expose the bottom of her tits before reaching under and squeezing them together. Leaving the tight yellow fabric stretched around her bustline, she pushed her hips forward running her fingers down her stomach and slowly unbuttoned her jean shorts.

She teased the top of her purple silky panties, spreading her shorts open and allowing her fingers to disappear underneath. Once again she turned around and slowly worked her tight shorts off her plump ass, bending over and taking her thong down with it. As her shorts hit the floor, she stuck her butt out and grabbed her thighs open, the sound of her wet pussy slips spreading apart permeating through Beyonce's chorus.

Turning back to face me, she stepped out of her shorts and thong and peeled her tank top over her head, tossing it in my face as she lifted her leg over me onto the couch. I lean in as she glides her finger up and down her ample lips, fishing my arm under her leg, clenching her ass, and pulling her pussy to my mouth.

My free hand danced up her stomach and onto her nipple as I pulled her ass, smashing my mouth onto her dripping twat. Running her fingers through my hair, she rocked forward, her eyes fluttering. Grabbing my hair and shoving me back, she snaps, "fuck me."

Rock hard and ready to go, I unbutton my shorts as she turns around and presents her ass to me, balancing herself with her hands on the coffee table. I tear off my shirt, stand up, and pull my cock out of my boxer briefs, allowing my shorts to fall around my ankles. Her legs are a little long so I tap the inside of her ankle with my foot, spreading her legs wider so I can get the right angle, slipping fully into her sodden canal.

Clamping onto her curves I pounded her depths completely, ever so slightly bottoming out with every stroke. Enough to completely fill her up, but not so much to cause any pain. Like I said, we fit well together. The sexual tension and excitement had me cumming pretty quick - just long enough to lose our breath and crack a bead of sweat.

My hard fast strokes built up a froth around my shaft as I wrenched her hips back into me, firing like a cannon against her walls, my knees shaking and weak. I fell back onto the couch as a gulp of cum poured out of her gape, oozing down her leg as she panted and stood back up and jiggled back into the kitchen for a paper towel.

"You're a pretty good stripper for never stripping before."

"I never said I've never stripped, I said I've never stripped for anyone else."

"So you strip for yourself?" I laugh.

"No" she giggles, "I took a class years ago. Was supposed to be a present for my husband, but, well, you know how that worked out."

Shortly after, the drugs took hold and we cuddled, laughed, and giggled on the couch for the rest of the night. We woke up in the middle of the night in the middle of sex - one of those, "who started it?" sort of things we all love. Fucked again in the morning and I was sold. She was my new girlfriend.

For the next couple of months I stopped dating and we saw each other every Thursday and occasionally on the weekend, which is all our schedules allowed. Right about the time when we were talking about introducing each other to friends, she grew tired of the superficial nature of my relationship strategy and broke it off with me. It kind of sucked, but I wasn't too broken up about it, on to the next!

Date #52 - Mal the Comedian

Mal was my first real success story outside of the online dating world in a long time. Frankly, with how busy I could be doing everything online, hunting in the wild just seemed like a waste of time. On one hand, it's much easier to build attraction. On the other, in the online world you know there's a baseline attraction from the start and everyone is open to dating whereas in real life, most women are either not single or just aren't interested.

I just sort of fell in with Mal.

A buddy of mine had been talking about doing stand up comedy for a while. I'm a naturally funny guy and always thought (incorrectly) that I could do well as a stand-up. One Wednesday evening when I didn't have a date planned, I sent him a text confirming he was going to the open mic and I was going to join him.

I noticed Mal right away as the most attractive women at the bar. She looked to be late 30's, tall, really busty, and had a sexy librarian thing going on with her black horn-rimmed glasses and dark hair pulled up in a clip. I had my eye on her throughout the show and when my buddy did his set, he gave me the opportunity.

The bar was a dive and there was a funky odor in the air that night. He made a comment about it from the stage and Mal blurts out, "well your friend over here is wearing flip flips!"

That got as big of a laugh as anything that night and immediately had me questioning my toe hygiene. With some nonchalant olfactory investigations it was determined that my peds weren't the issue so when the show ended, I made my move.

"I'm going to need you to smell my feet so I can prove to you that my flip-flop situation is not a problem here."

Mal spun around, took one look at me, and burst out laughing.

"No way I'm smelling your gross feet. I have a thing with smells."

"Good smells or just bad smells."

"Your feet don't smell good."

"They don't smell at all, however other parts of me do smell good."

"Oh yeah?"

"You tell me."

I lean forward deep into her personal space, extending my neck past her face.

"Go ahead."

She laughs, then murmers.

"Ok, you pass the test."

"Oh, we're testing now?"

"Always."

"And what are some of these other tests? If it's essays, I'm out. I only have time for multiple choice, at most."

"Just observational, except one."

"What's that?"

"I like butts too."

"It's your lucky day because I, happen to have one. Take it everywhere I go. See?"

I spin around, push my ass towards her and shake it back and forth.

"Whooo!" she hollers, giving me a slap.

"Hey now, touching is extra."

"You're extra."

"You have no idea."

As we continued talking and flirting, I noticed she was definitely a bit older than I originally thought. Turns out, she's 46 and, the kicker, she's got SIX fucking kids. Wow, I was not expecting that from someone who's body was in that good of shape.

We talk about being single and what we're looking for - I acknowledge that I'm here for a good time, not a long time and she's down with that so I tell her to find me later when she's ready to make out. She laughs, and I walk way to reunite with my buddy who's smoking a joint on the back patio. Mal shows up shortly after and sits at our table, lighting up a cigarette.

Then she proceeds to talk endlessly, running off most of the people around us, my buddy included. There's only a handful of us remaining on the patio and I'm really tired of hearing her talk, so I excuse myself with an offer.

"I'm going to leave now, if you want to make out, let's go."

"I can't right here." Mal advises, pointing up at the camera in the corner.

"Who gives a shit? You think they're going to jerk off to it?"

"No, but I know everyone here. Just walk me to my car."

We make our way through the parking lot, to a secluded corner behind a full size van where her car is parked. Immediately we start kissing and I'm happily surprised by her skills.

"I'm glad you're a good kisser," I say in approval.

"You're a REALLY good kisser. I was not expecting that."

"I'm good at a lot of other things too, wanna see?"

"I do, but it's late."

"Another time then."

We resume making out and my hands wander her body. Popped her jeans open, roaming the undergarments. Nice and shapely, big bolt-ons that reminded me of Kinsley and a nicely trimmed pussy that was dripping before I even touched it.

"Ok, that's enough for tonight. If you keep touching me, I'm going to fuck you and we can't have that."

"Definitely can't have that." I scoff.

"Not tonight at least."

"Ok then."

I plant another one on her, grab big handfuls of her ass through her jeans, give it a little slap and walk away.

Nothing more really happened with Mal after that. I'd run into her a few more times over the last couple years when I go fail badly at comedy. Seen with a couple of boyfriends and tried to pick up her friend one night before giving her a hug on my way out and lick-biting her neck. Just kinda fun as I don't really have much interest other than the flirt we have going on.

Date #53 - Christine Myers

Ok, so Christine's last name isn't Myers, but I realized that she looked like my friends growing up who's last name was Myers. Looked so much like them in fact, that it totally freaked me out and ruined everything. Not really everything, personality ruined it too, but the sex was great.

Online dating is always a roll of the dice, you never quite know what you're going to get. With Christine, I got sexy sultry in pictures and similarly sexy sultry in person, just flavored in the Myers family who lived down the block from our high school. 5 boys and this was probably their long lost sister somehow.

Anyway, the swipe, match and texting weren't anything to write home about, but she seemed fun so I set up a date. Christine didn't drive, so I agreed to pick her up at her place. I pulled up, sent her a text and decided to go up and ring the bell. Standing there for a couple of minutes, I get a text back, "it's the apartment in the rear."

I walk around back to see a tiny little house, the size of a large shed. She pops her head out and immediately I recognize the Myers in her. Late 30's, shoulder length black hair slightly kinked up, olive skin, and a hot little rasp in her voice. Definitely some sort of latina, but I never asked which flavor. If she didn't remind me so much of my high school friends, she had a lot of good going on. Definitely pretty, quite thick in all the right places, hiding some cute handfuls in a Joan Jet t-shirt and wearing painted on jeans that couldn't hide anything.

After initial pleasantries, she fed her cat, finished the Modelo tall boy she was drinking, and we jumped in my truck to hit a nearby bar. My original plan was to check out the one restaurant in that area I had not yet taken a date to, but as it turns out, that's where she worked so it was definitely a no go. And, is now forever a no go.

We had a bunch of beers and ate bar food, laughed and flirted a bit. Somehow we got on the subject of kissing and by this time my hand was already on her thigh, so I just leaned in and kissed her at the bar.

"Woah, I was not ready for that."

"For not being ready you sure were kissing me back."

"Oh no, your timing was great, I just didn't expect you to kiss that good."

"I am a man of many talents."

"Are you now?"

"Is that a challenge?"

"Maybe."

"Fuck around and find out."

"Ok, let's go."

Just like that we were heading back to her place. She grabbed us both beers and I'm not sure either one of us even drank a sip. Her apartment was an efficiency so the only place to sit was on her bed, which ended up quite convenient.

I kicked off my shoes and made myself comfortable, laying across the bed as she fumbled with the remote for the TV. Scrolling through the guide she sat down in front of me and I reached up, grabbed her arm, and pulled her back onto the bed. She rolled to meet me and as we kissed she wrapped her thick leg over mine.

She was a great kisser and getting really riled up quickly, grinding herself into me as I got hard. Passions grew as I lifted her shirt, slid my hand up the back, and unfastened her bra.

"One handed? Really?"

"A man of many talents."

"Stooooop."

My hand ran down her back and into the space her massive booty causes to always remained open at the top of her jeans.

"No underwear? Really?"

"I have talent too."

"I don't think laundry day is a talent."

"Shut up" she giggled.

Plunging my hand deep down her pants, cupping overflowing handfuls of cool, soft, silky skin, I feel her hand stroking me through my shorts. Reaching between us, I unbutton and open my shorts, pulling down my underwear to give her access.

"A man of many talents" she purrs.

"I aim to please."

Undoing her pants, I push them down and she begins to wriggle herself free. I pull my shirt over my head and help strip hers, then I slid my bottoms off as she takes me into her mouth. She works me up and down with solid technique and fervent enthusiasm.

With a pop she pants, "do you have any condoms?"

"In my truck."

"It's ok, I have some."

Giving me a couple more strokes and a quick kiss on the tip, she scurries across the room with her big butt hinting at dimples as it shakes, reaches into a drawer and returns with a three pack.

"Three? That's ambitious."

"That's just how they come, but I thought you had many talents."

"Touche."

Stretching the rubber over my cock, she hovers above me on the bed, her ample curves glowing in the pale light of the muted TV. Crouching down, she guides me inside of her hot little hole. Rising up and down she planted her hands onto my chest and lifted up and down with long, slow strokes. My hands lifted her thighs from underneath as I gyrated my hips to meet her pace.

"This is exhausting."

"Bend over."

"Oooo."

I roll off the side of the bed as she buries her face into the bedding and sticks her ass way up in the air, it's bulbous heft oscillating like overly firm Jello. Grabbing thick handfuls of ass, I push my dick into her as she digs her nails into the comforter. Fast slaps have her squealing into the pillow and my cock pulsating with intensity.

"Deeper"

"On your side."

She falls to her side and I push her knee up, straddling her other leg and working myself into her tight little sliver. I grind myself in fully, reaching over and grabbing her full B cup's with big thick nipples and generous dark brown areolas.

"Yes, that's it."

As I build intensity she forces the pillow over her face and screams like she's being murdered.

"OOOOOOOHHHHHHHH FUUUUUUUCK!!!!!"

She cant handle it and just as I'm starting cum she launches herself up the bed, trembling in a heap, and whimpering breathlessly. A couple of quick strokes to finish myself off and I'm stepping off the bed to throw the condom in the trash.

"I can keep going, I just need a second."

"I finished."

"Really? When?"

"Just now."

"You mean after?"

"Yeah."

"I'm so sorry!"

"Ha! it's no problem, it was still good."

"If you're not in a hurry, there's still two more condoms." she laughed.

"I guess I'm not in a hurry."

Drank our half warm beers and cruised though a little bit of TV, spooning until junior started to stir again. Half hard and drooling between her impressive cheeks, I began lightly rubbing myself up her crack. She got the memo and began turning her hips back and forth, filling me up with blood and working me deeper into the crevasse.

Reaching up to the window sill, she rips off another condom as I run my hand over her stomach and across her tits, nibbling and biting her neck and ears. Rolling over to kiss me, she unfurls the condom over my length and pulls me on top of her.

Rising up on my knees, I popped the head up and down her opening, trimmed with short neatly groomed hair, I tease her a bit before pushing it inside. Her nails clawed down my forearms as I find bottom and begin thrusting. Hoisting myself over her, she clings to the back of my arms and arches her head side to side while her moans grow louder.

Within a couple of minutes she's full on screaming and nearly convulsing with every movement. My body slaps against her thick thighs and her little tits rock up and down. I lean back, pushing her knees down to her chest and watch her little belly heave with every breath as I lose sight of myself inside of her.

The sweat builds on my brow as I rapidly impale her, the heavy clapping sounds of bodies in sex mostly drowned out by her 'oh's echoing through the room.

"Oh my god!"

Once again she dives up the bed, a quivering mess.

"God, you're really good at this."

"Talen..."

"I know, I know... are you about to cum?"

"Not even close."

"I can't do it any more."

"That's ok."

"I'm definitely going to finish you off."

"Much appreciated."

I lay back down, peeling the condom off and giving myself a few strokes as she makes her way to me. She nibbles my nipple and tugs me briefly before moving down and taking me back into her mouth. Nice and sloppy with ample hand action, but it's hard for me to cum with just a blowjob.

"Are you close?"

"No, it's hard with blowjobs."

"Ok, but my jaw hurts."

"We can always just rub."

"What do you mean?"

"Just grind, no insertion."

"Interesting."

"It's fun, get on top."

She lifts her thick leg over me and scoots up until her moist warmth gently glides over my straining shaft. With slightly increasing pressure and more lengthy strokes, she starts really getting into it.

"This feels really good" she whispers.

"It's one of my favorites."

"I can't believe how good this actually is... it's really turning me on."

Just then she leaned all the way forward, lifted her ass, reached between her legs and guided my raw cock inside her feverish pussy, kissing me hard.

"I hope that's ok."

"It's already done."

"Sorry, it's been so long" she pants into my mouth, slowly raising her hips.

"How long?"

"4... no... my god, almost 5 years."

"That's a long time"

"Oh FUCK this feels good."

Sitting up, she grinds back and forth, every so often bouncing up and down.

"I want you to cum in me."

"Is that a good idea?"

"I'm on the pill."

"So... a great idea."

"Yeah" she breathlessly moans, her head rolling back and body shaking.

"Crouch over me and fuck me that way."

"Like we started?"

"Exactly."

Sitting back hard, she brings her leg up in front of herself and dismounts my glistening manhood. Reaching under and delicately directing it, she squats down on top of me.

"Up and down... yeah, just like that."

"Oh god... shit... oh... oh... oh... OH MY GOD!"

Just as another orgasm rips through her system I begin to cum. I force her thighs down so my cock is at maximum depth and blast into her, my firm grip not allowing her to escape this time.

"OH OH OH OH OOOOOOOOO OHH GOD."

She's a complete mess on top of me, ever fiber of her being twitching in pleasure and she falls backwards against the wall, contorted in the corner.

"I'm going to pass out."

"Ok, probably time for me to go."

"Yeah it's late."

And those were her last words to me. I knew it wasn't going anywhere, but the sex was pretty great and I could look past the family resemblance for a while. I guess she had different plans. I sent a text letting her know I got home and then I never heard from her again.

Date #54 - Clara the Prude

I previously named Hannah the prude, quite unfairly. Clara, however, was a prude.

Clara was a total cutie, early 30's, thick wavy almost messy looking blond hair, natural beauty with no makeup and at 5'6" carried a nice bit of curves despite being pretty lean. She was a freelance writer who was routinely published in several big magazines. If you've been to the doctor's office in the last 5 years, there's a solid chance you've seen her work in stack of magazines in the waiting room.

She's traveled the world, living mostly in tropical paradises, but grew tired of short term relationships and missed 'the feel' of the US, so she planted herself here for a few months to figure out if this was a good forever spot.

We had a great vibe and went on fun dates, but when it came down to anything physical, it was completely hands off. No touching. Of course, I'd break the touch barrier, while she didn't recoil in horror, she also never reciprocated. And the real clincher - she wouldn't kiss me.

Three dates and no kiss. I felt the vibe on the physical during our first date, so I didn't even try. That vibe didn't really change, but sometimes you just have to shit or get off the pot, so I went for it at the end of date number two. Again, no recoil or objection, just zero kissing back. On the third date we actually were at a spot really close to her place and we got a little tipsy, so when I walked her home I was really wondering if something was going to happen.

Nope. Nothing.

Get to her place, she thanks me for another great date, and I once again go for it. Same thing. Like kissing a stone.

"Why don't you want to kiss?"

"It's too soon."

"Too soon for kissing?"

"I'm still trying to figure things out."

"Honestly, kissing is a huge thing for me and if it's not good, I'll lose interest."

"I understand."

"Ok, well you take care of yourself."

"Are you breaking it off?"

"Yes, I'm sorry, I thought it was clear."

"Wow."

"Look, the physical part is a major part of the equation. If that doesn't work, none of it will work with me."

"I don't disagree, but why rush to the physical?"

"I'm not trying to fuck you today, but a kiss can tell you a lot about your sexual compatibility."

"You think so?"

"Absolutely."

"I'm not sure about that."

"Hey, it's fine. This is what dating is all about. We find out how we're compatible and how we're not and weight it on balance then open ourselves up to each other. Kissing is a big thing for me. Just seems we're not compatible in a fundamental way."

"I guess not."

She was definitely a different one and I've caught a few of her articles in various waiting rooms. Needless to say, her content is not sex and relationships.

Date #55 - Mayra the Soft

Everything about Mayra was sweet and soft. She had soft features, spoke softly, was dainty in her mannerisms, and had a soft, curvy body. Originally from Venezuela, she moved to the US when she was a teenager and now in her early 40's, even her accent was soft.

While she did have a couple of kids at home, she had a good bit of free time since they lived with her ex-husband over the summers and we met just before they were out of school. I liked her pale skin and how her makeup was very light, but always wore striking lip colors that popped due to her fair complexion. The jet black hair bobbed just past her chin provided more contrast. She was 5'6" with plump handfuls, a nice plump ass, and just a bit of a belly - soft and curvy... sexy.

After some laughs over dinner at a high end casual seafood place, we hit the beach across the street for more wine and a little frolic. Like everything else about her, Mayra was a soft kisser. Not a bad kisser, but just not forceful or incredibly passionate. We kissed, I roamed, and as my fingers became dampened on her soft hilt from under her dress and my member strained to the graze of her neatly manicured nails over my shorts, she retreated, insisting we save more for a second date.

We met a few days later at a spot she liked right across the street from her job as a regional executive for a major international bank. She couldn't commit to anything more than dinner since she had to travel early the next day so we had a few laughs, a few tacos, and made out in her car for a half hour before she had to go. Nothing especially notable about this date except for her casually dropping interest in being friends with benefits. So casual, in fact, that I didn't even realize she had lobbed that softball until I was about halfway home.

When she returned from her trip she insisted we meet up for the weekend. She was back at work on Friday, then wanted to come straight over to my place after. She was pretty aggressive, which seemed out of character and a definite contrast from the submissive softness vibes she had given up until that point. Offering to take care of dinner so long as I had wine, she made it clear that she was staying the night.

Just before 7pm she shows up looking professional in a white silk blouse, black skin tight skirt just above the knees, matching mid-heels, over sized sunglasses, and four bags of groceries.

"Didn't forget anything did you?" I laughed.

"In my car... where's the kitchen?"

I directed her to the kitchen and retrieved her suitcase from the open trunk of her Mercedes. I wheeled it into the living room and came into the kitchen, where Mayra was a whirlwind of activity. She already had a pot and skillet going on the stove and was slicing some flank steak.

"Make yourself at home."

"Are you upset that I'm cooking for us?" she retorted wryly.

"Not at all, but didn't you mention keeping this a bit more casual last time?"

"I didn't have time for lunch today and haven't had a real meal in days so you get to eat good too."

"And you're spending the night... that feels very girlfriendy."

"I just like sex when I first wake up, is that a problem?" she responds, still not turning around from her butchery.

"Only if waking up in the middle of the night to have sex isn't a problem for you." I say, pressing myself against her, running my hands up her body, squeezing her chest and licking her neck.

She giggles, lets out a little sigh, and turns to kiss me.

"Go sit down, this will be done in a minute."

"You don't need any help?"

"Men don't belong in the kitchen. Sit, relax, pour us some wine."

By the time we started eating we were already down a bottle of wine and didn't make it past our first glass of the next bottle throughout our meal.

"Are you ready for dessert?"

"Did you bring something, or are you going to make it?"

"I brought it. Come see."

She smiles and stands up, tempting me with her finger in a come hither motion. She prances ahead of me.

"Is this your room?"

Before I can say anything, she's through the threshold and pulling up her skirt, exposing her jiggly white butt highlighted with garters, stockings, and a cheeky thong.

I skip in behind her, wrapping my arms around her stomach and chest, grabbing her throat and licking her neck, then nibbling her ear. She presses back into me, softly moving side to side, rubbing her cheeks across my growing interest and reaching back to harness the back of my head.

I hike up her skirt fully above her waist, running my hand down the front of her silky underwear, teasing over her dampening hilt. My other hand races up her shirt, shoving her bra up her chest and squeezing hard on her soft handfuls while the nibbles on her neck turn to scraping bites.

She spins around, reaching down and lifting my shirt. I raise my arms as she pulls it over my head. I stretch back, pull down her skirt as she shimmies. I unzip it and it falls to the floor. She's fiddling with my belt as I unsnap her bra and begin to pull her shirt over her head. As she tosses it to the side, I'm dropping my shorts and pushing her onto the bed.

Mounting her, I kiss and bite her lips as she rakes her nails up and down my shoulders and arms. My hard cock presses against her trembling stomach. She finds the waistband and begins to push down my boxers. I roll off of her, reorienting myself properly at the head of the bed and pulling her to me. She stretches my underwear and peels them from mid thigh. I kick them into the ether.

She delicately holds my member between her thumb and forefinger, slowly taking me into her mouth and softly sucking. A little more. A little further. I reach the back of her throat as her easy touch, tightens around the base and soft slurping sounds drift through the dimly lit room. I extend my hand under to cup her cute little tits. Nice soft handfuls, cute little areolas, long thin nipples hang softly in my grips. I tickle down her side, reaching hard to get a handle on her ass.

She walks her back end up the bed and into my clutches. I rub her soft smooth skin, gliding my fingertips over the slick mound burning through the silk fabric. I tear at her panties, pulling them partially down and ripping them at the waistband. She kneels up, stroking my cock and staring down at me, then flops next to me, wiggles herself out of her panties and kicks them from her ankle.

I roll to her, but she pushes me back, kissing me as she climbs on top. She sits back, her pussy spread wet and enveloping my shaft. She grabs my hands from her thighs, intertwines our fingers and brings them to her chest. Grinding, she slips forward just a bit, then back, effortlessly guiding my compass due north to her buried treasure. She's hot and busy, massaging my hands into her tits, grinding my cock into her depths, and softly moaning as her head throws back, her short bobbed hair sticking to her face as it rotates side to side.

She was methodical, but not boring. She created interesting angles with her hips and kept her strokes varied, making me feel like I was on the verge of cumming without letting me go. It wasn't raw passion or seductive pleasure, it was something different. A soft comfortable build up. A slow burn towards the main event. She teased the edges of fucking and making love, while clearly working herself into her own euphoria using my dick as a tool.

While nothing hard or fast, she was in constant motion. Her body flexed on top of me and her tempo slowly built. Never past a medium pace, she worked me for 10 minutes before she began to relent. Covered in a clammy sweat I could feel as she directed my hands around her body from her tits to her belly, to her thighs, ass and throat. She breathed hard, but steady. I sat up, wrapping my arms around her sweaty back and pulled her to me. Her heavy breath panted into my mouth as I pulled my knees up, planted my feet, and took over the workload.

Her hips ground in circles as I began offering slow short strokes. She stiffened and locked in as I drew further, faster, harder. Thumbs in the creases of her hips, hands welded firmly in place, teeth gnashing together in forceful kisses, I smash myself into her completely, our perspiring bodies slapping and sliding against each other. She moans loudly, holds her breath, exhales hard, and convulses onto me, her little hole locking like a vice as she cums.

"OOOOOOHHHHHHHH!!!!!"

A deluge of liquid soaks me to the bone. She squirts uncontrollably as I pound wet sponge sounds from between us. Relentless, the splashing runs completely between us. *SLAPSLAPSLAPSLAPSLAP...*

I'm dying to cum and completely numb. She's going limp and I'm breaking concrete, gasping for air. I slow, stop, take several deep breaths.

"Did you finish?"

"No, I just need a breather."

"I can't anymore, let me help."

She slides off of me, reaches down, grabs my sodden member and twists and pulls, giving me exactly the type of new sensation I need to regain some feeling. She strokes me softly, with touches of firmness that really gets me peaking.

"Are you going to finish?"

"I want to fuck you again."

"Ok."

"On your stomach."

I direct her onto her stomach, kneel beside her stroking my cock, and throw my leg over her. Massaging her ass, my thumbs part her cheeks and I guide myself between her legs, back into her soft little honey pot. I lay on top of her, grinding her soft, plump ass; feeling the cool dampness of her previous squirt drying on her ass. She locks her legs together, then crosses them, pinching me tight. I rise back up, locking my hands on each cheek and watching my girth slide in and out. Moments later, I feel myself letting go.

I wrap my feet under her legs and lock myself as deep as I can be, both of us completely clenched as a 21-gun salute empties from my balls and coats her insides. We relax, lay beside her in a mess of sweat, sex, and her spraying orgasm.

"Do you normally squirt?"

"It happens sometimes."

"Glad I have a mattress protector."

"We're definitely going to need it."

Except, we didn't. Part of what got so tedious with Tanya (Date #40) was the constant bedding laundry. I really didn't want to get into all that again. I gave it another go one night about a week later with the same results. Mayra said she didn't expect it every time, but my dick hit all the right places and stretched her well enough that she knew she could always cum with me. And that meant, more squirting.

So, I allowed us to slowly fade. She never asked, I never offered, and eventually one of us just stopped responding. Shame too, cause she would have been an excellent friend with benefits. She makes dinner, fucks my brains out, then leaves. Talk about ideal.

Date #56 - Sabrina the Meatball

This lil rasphy voiced cutey was a total meatball in all the right ways. Not even 5' tall, blond hair just past her chin, mid-30's, built like Christina Hendricks if you removed 6" from her torso, arms, and legs - like god had leftover tits and ass pieces, but not enough arms, legs, and torsos. She just looked fun.

Her profile was ho-hum, every picture she was making a funny face, demonstrating her personality and hiding the fact that she did appear prettier in person. We ate dinner one of my go-to spots near the beach and she just pushed her food around her plate, never finishing her glass of wine. I figured this was because she was conscious about her weight.

After dinner, we walked to the beach, threw down a blanket and uncorked the remainder of the bottle from the restaurant. We talked a little, started making out, and just as my fingers really started to play with the edges of frisky, she paused and burped in my face.

"OMG, I'm so sorry."

"That's an interesting kissing technique" I joked.

"So embarrassing. It happens after I eat."

"You barely ate."

"I know..."

She went on to tell me she is recovering from lap band surgery. In sort order that fun highway of curves will melt into a mudslide of destruction. I've encountered this a few times during the chatting stage - usually comes up when I start making dinner plans. It's great when people take their health seriously, but the thought of all that skin just turns me off.

We kissed a bit more and a little misting rain saved the day. If things were going well, I'd just roll us up in the blanket, but at that point I was ready to roll. Walked to her her car, ended with a hug, and later that night told her I wasn't feeling it. Shame too, cause she was exactly the right kind of chubby.

Date #57 - Jennifer the Positive

Speaking of thiccums, Jennifer had it going on. In a different universe, she had long term potential written all over her. In fact, by the 3rd date, I was already thinking girlfriend and so was she. It didn't work out that way though.

Jennifer was a total sweetheart and damn sexy. 5'10", early 30's, shoulder length blond hair, cool blue eyes, a cute natural smile, nice big hangers, and hips and ass that looked like she was trying to shoplift a few sets of pants from the dressing room at Target. Very wholesome looking, but had a slight edge about her. She didn't wear a drop of makeup and absolutely didn't have to. She had a great outlook on life and just had that low key charisma that you might miss if you weren't paying attention, but once you see it, she's just magnetic.

We ate dinner at an Italian spot I like to take dates to by the beach sometimes. When she showed up, I was totally hooked. She was wearing a little sundress that let her jiggle just barely filter through as she walked. We ate, had a pretty standard "good first date conversation" then we hit the beach.

Standard fare - blanket, wine, kissing, touching. Things were going well and despite thinking I could probably push things further, I kept it PG-13 and played outside of the clothes. Her big ass was the perfect consistency for some squeeze and shake which quickly got the lower unit humming.

The bottle of wine was kaput and it was getting late, so we called it and I walked her back to our cars. Another makeout session, booty jiggling shake as she got in the car (I believe I even said, "god damn look at that thing") and a second date was booked.

More of the same on this one, though we just walked and talked on the beach. We held hands, got flirty, but never really made it past making out. She was a good girl in that way, but did open up about her affinity for recreational drug use, which I certainly appreciate.

The third date was groundbreaking. I felt us getting closer and closer every step along the way. We met for a quick dinner, then onto mini golf, where things really escalated. Our fun and loose flirty conversations got a little more serious and we were just totally comfortable with each other. It felt natural, with her positive energy, like it was the start of something real.

After I dominated golf, we ordered some ice cream and went to the bathroom to wash our hands. The mens room was occupied so I just followed her into the ladies. To my surprise she wasn't just washing her hands, she dropped trow and peed as I hit the sink. I apologized for intruding and she just laughed, saying she saw where this was going and it wasn't a big deal. She was so sweet and positive, like nothing could shake her.

When she stood up, she angled her ass towards me just a bit, did a few hops to stretch her milky white heft into her tight jeans, leaving just the slightest hint of dimple as the tough fabric burst over and onto her waist. Her ass is what the Kardashian's were going for when they ended up with diaper butts. Top 10 booty's I've ever played with.

We ate our ice cream and once again, hit the beach. This time with my backpack in tow - I was positive things were definitely getting hot and heavy tonight. I was right.

A little chatting then straight to business. Kissing, playing, I'm hard as a rock, opened up my shorts to give her full access, up her shirt, bra unfastened, pants unbuttoned, my first feel of that glorious ass as she strokes me out of my underwear and into the cool night breeze...

"Wait."

"What?"

"I see where this is going."

"Me too, I like you. I think we might have something here."

"That's not what I mean... I mean, sure, but there's something I have to tell you before we go any further..."

"You have a penis."

"No... it's..."

"Look, as long as it's smaller than mine, we're good..." I tease as she really starts to tense up.

"My ex husband cheated on me and gave me HSV."

Herpes. Simplex. Virus. Brake check!!!

Hot and heavy got cool and limp in a quickness as we discussed the implications. At that point she just advised me to do my own research and, "will totally understand if it's a dealbreaker."

That night and a good portion of the next day, I did my research... and it was a dealbreaker. Turns out it's one of the few STD's that are easier for men to get than women, condoms aren't very effective, and despite her being outbreak free for 6+ years and being on a suppressive drug, there's still a good chance for me to get it.

What really surprised me was how difficult of a decision it was. Granted, we'd only been on 3 dates and if it didn't work, having to have that conversation with every woman I wanted to have sex with would be excruciating. I just couldn't do it and the girl with the positive outlook on life to match her positive test results, was in the rearview.

Date #58 - Drea the Familiar

Too familiar.

Drea was a late 30's, never married, no kids, Brazillian woman with a body that could stop traffic. Her face was cute enough, but at 5'6" with a thick bronze body and long black hair, this executive chef was hotter than the sun.

We met at a little bougie boutique seafood place on the beach where she took apart the menu and everything we ordered. It was like watching one of those reality chef shows. She impressed the waitress so much, we got at tour of the kitchen and she, and the owner/chef, talked shop for damn near 20 minutes. It wasn't bad though, she was into me and I thought it was pretty cool how much knowledge she dropped.

We hit a little dive bar next door and through a bucket of Coronas, I figured out the thing that was off with her all night. I kept looking at her and thinking, "she's so sexy, but..." and I couldn't put my finger on it. Just as it was time to make the call on another bucket it hit me - she looked like my buddy's wife.

Not a spitting image, not even near it. But something about mannerisms and how she carried herself screamed her name. You'd never think they were sisters, but I'm convinced if you hung around with them long enough, you'd think they were related or otherwise really close. Now, it's not that I don't think both are attractive, but they weren't sharing the good parts with each other.

So, no more buckets, just a walk to the car where the little head took over and I went for a kiss. A little make out sesh, some pawing at her tight round booty, and it was over. She didn't text and neither did I.

Date #59 - Kit the Pitcher

The best part of this date was seeing Mal at a the tiki bar spot and us making eyes past our dates and flirting without being caught. Small world, I'm surprised I don't run into more women I've dated given the hundreds of dates I've been on. Though, at this point in my dating career, I was starting to be noticed a LOT by the service staff at some of the places I liked to frequent. It's never been a problem, though I've had a few close calls.

At any rate, Kit was a lot of fun. Brand new single; separated and still living with her husband - my specialty. These situations are perfect because I'm a ton of fun, they're not ready for anything serious, and there's a ton of pent up sexual energy. Once you get that ball rolling, sexy time comes really quick and the novelty of someone new makes them really, really get after it.

Standard "lake date" as I started to call it. Dinner at one of the four or five restaurants near the park surrounding a lake, a walk around the lake, a night cap at the basement bar, tiki bar, or taproom, then getting frisky in the parking garage.

And that's exactly what we did - Mexican, lake walk, tiki bar, parking garage fun.

Kit was a beauty. Short, late-30's, long straight blond hair, bright green eyes, touch of freckles across her nose and cheeks, a big gorgeous smile, and a set of hooters that looked about two sizes too big for her short curvy body. She was energetic and spunky, full of laughs and silliness. Even when she discussed her soon to be ex, she said her piece, kept it light and funny, and didn't dump like a lot of women do. I always found that gross and made me question people's character who dump on their ex.

She had one of the more interesting jobs of my many dates. Kit was a professional softball pitching coach. Her entire job was running camps and programs for high school and college girls, and working with individual teams across the country periodically. She'd fly out to California, work with a college team for a month, then return and run a camp where girls from all over the country would come. Apparently, Kit was a legitimate coaching badass. Super cool and so were them tittays.

We had already kissed a little at the tiki bar (after Mal had left, I'm a gentleman), so when we returned to our cars in the parking garage it was on. Years of repressed sexual energy poured from her as we kissed hard and sloppy under the flickering fluorescent lights.

Kit was a solid kisser and just clawed up and down my chest and stomach the whole time. My hands played around her soft curves, eventually sneaking their way under the back of her shirt and down her jeans to her modest ass tucked under some plain stretchy panties. I worked my way around to the front, flipping up her bra and milking her vast hangers before sliding down her fluttering tummy, toying into her waistband.

I could feel her drawing in her stomach and giving me access as she sucked hard on my tongue and dug her nails into the top of my chest. I thumbed open her top button and pulled, forcing the zipper down and allowing my wandering fingers to breach the top of her panties. Greeted with the soft felt of a neatly trimmed mound, my fingertips sunk into a gushing mess of pussy. Soft, plump, hot, she wriggled as my fingers swirled around, gently increasing pressure, but pulling back when she tried to force it.

Throwing her arm around my neck and reaching down to grab my wrist, she thrust herself into my hand and I cupped hard on her pelvic floor, my middle finger slipping deep inside her burning little pussy. Breaking from our kiss, she pulled me in and bit hard on my neck and my other hand drove down the back of her underwear to clamp the bottom of her ass and give me leverage to penetrate her depths.

She breathed hard into me as her sopping twat poured from my probing. She finally released my wrist and snatched my girth on the outside of my pants, yanking wildly and falling back into her car. The juice from her pussy had spread throughout her panties making me think she squirted, but the slickness told a different story.

As I ran deep circles into her wanting vulva, she began tugging on my belt. I pulled my dampened hand from the back of her jeans to assist in her goal. With junior free, I palmed her driver side window, leaning into her as we masturbated each other vigorously.

We were exposed. Well lit, public, anybody could drive by or walk through at any moment. We stared at each other, momentarily kissing, sucking a lobe, biting a neck, or just breathing hard in each other's faces. She shuttered and buckled as she came, gulping and panting with a light whimper, twisting her body to remove herself from my probing fingers.

Wrapping both hands around my bulbous erection, she stared into my eyes and deftly twisted and pulled. I hovered over her, both hands planted to the side of her car as she worked diligently to finish me off. I stiffened, my knees began to shake. She pulled me down, stuffing my cock into the top of her soaking wet panties. I bent my knees, feeling myself slide past the cold of the evaporating juices on her fuzzy hilt and into the slippery hotness between her thighs. She reached around my back pulling me in while stroking the base of my shaft until I exploded between her legs into the bottom of her panties.

"I wanted to feel you cum." she panted, as my cock slipped from between us.

"That was different."

We began pulling ourselves together.

"I was so ready to fuck you, but this isn't the place for that", she offered.

"We came pretty close."

"Very close."

"I guess that means date two is going to have to be a little more private."

"Much more private."

We kissed for a couple of minutes, wiped my pussy sauce handprints off the side of her car with some napkins I had in my glove box, and went our separate ways. I texted her to make sure she got home safe. She texted me that she had a great time.

The next morning I sent her one of my patented good morning messages and never heard from her again. Kind of weird. I've had dates go pretty well, then end up ghosted, but I've never had anything so hot and heavy where there was no sense of regret end up as a ghost. A few months later I saw Kit's profile pop up on social media. No indication of a husband or boyfriend or anything. Just some ads for her next training camp and a cute picture showing those sexy freckles.              

Date #60 - Mrs. [redacted] the Hotwife

[Apologies: Last minute decision to remove this one for privacy purposes]