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.