The 50-First Dates Ch. 01-10

She ground atop of me and we made out, my hands roaming her body, cupping her firm tits and soft ass.

"God I wish I could fuck you!"

"If you keep doing that, I'm definitely going to fuck you."

"Well then, I'll stop!"

Rolling off of me, she laid beside and began touching me all over. We kissed hard, our tongues lapping in unison and bodies aching for sex.

"Hold me."

Turning away from me, she pressed her supple ass against my desperate cock, circling her hips and turning her head back for my mouth. I wrapped my arms around her, feeling up and down her body, pinching her little brown nipples and massaging her stomach and thighs. Thinking of Bethany, I reached up and held her neck, testing the waters.

"Fucking choke me."

I squeezed.

"Mmm... really choke me...

I squeezed hard.

"No marks though!"

"That's going to be hard to do like this."

"Just not that hard. Just enough to make me feel dizzy."

I've trained Brazilin Jiu-Jitsu for almost four years, so I had just the thing for her.

"I can use a choke hold, but you have to tell me when to stop. Just tap my arm."

"Yes please."

I wrapped my arm around her neck, grabbed my opposing bicep, drawing that arm behind her head, giving her a firm squeeze.

"How's that?"

"YES. Just like that!"

She reached back and pulled on my dick as I very slowly increased the pressure. The harder I tensed, the more she tugged. She let out a little grunt and tapped my arm, releasing herself from my hold.

She huffed and puffed, swallowed hard.

"More."

I squeezed again; she wriggled her ass into the pre-cum spot on my tight boxers. I choked harder.

*tap tap tap*

"Uhhhh" she heaved, "let me catch my breath."

Her hand found my cock again, breaking the waistband and fitting into her hand.

"God I want to fuck you."

"I can do that."

"I can't, sorry."

"This is fine."

"Choke me again."

She was lightly stroking me as I clamped down hard. She gurgled for a second and gripped with purpose on my girth.

*tap*

Breathlessly, she pulled me out and held me between her cheeks, grinding up and down.

"More."

I squeezed again, just as hard. She shuttered and flailed, tapping immediately.

"Oh fuck"

"Too much?"

"No, it's perfect."

She lifted her leg, reached under, dragging my fat helmet down her thonged crack and clamped her legs around me, holding it against her red-hot pussy, burning through the thin black lace.

"Again" she panted.

I squeezed, she ground my cock, and she tapped.

"More."

The same.

We repeated this several times and her taps came slower and slower. Her hot pussy burned against my titanium as she shook, shivered, and masturbated me with her milky thighs.

"I need to stop or I'm going to fuck you."

"Like I said..."

"No, not happening. But let me show you what I'm good at."

She rolled over and slid down the bed to the floor on her knees, dragged her hair back up over my thighs, boxers, stomach and chest. She licked down to my belly button, pulling my boxers down along with my cock, allowing it to pop out with a satisfying slap against my stomach.

She tossed my underwear to the side, grabbed me with both hand and stared at it a second.

"You have a REALLY nice cock."

I laughed and she immediately took me into her mouth. She bobbed and twisted, wrapping her finger and thumb on the base to stroke me as she played with my balls with her other hand. All the way down to the base past her tonsils, she swallowed and slurped, then drooled over the tip as she handled the length of my shift with a full grip. Up and down, perfect pressure, perfect grip, perfect mix of hard and soft and not a hint of teeth. She wasn't lying. She was more than good at this; she was an expert.

I've had thousands of blowjobs from dozens of women in my life and I've never been a huge fan. On the good side of girthy, teeth are often involved and even when not, they just never did a lot for me. Angela converted me. Apparently, I've just never had a really good one.

She moaned and purred, expertly working my strained cock, knowing exactly when I was going to cum. Rapid bobbing turned full deep throat as I began to flex in her mouth. Every spurt was met with a deep, hard swallow as if she was trying to take my balls with her. She squeezed the top of my thighs and sucked, sucked, sucked, holding me perfectly in her throat and vacuuming the life force from my body. Easily a top 5 lifetime orgasm.

As if she was inside my brain, her suction softened along with my cock and by the time the blood had completely left my member, she was hardly holding me inside her mouth. I slipped out with a little kiss and she giggled, walking to the bathroom as my head spun. She returned a moment later and I began pulling myself together. I slipped into my boxers, then shorts and she handed me my shirt. She threw on an oversized shirt and walked me back outside.

A couple of her roommates were smoking on the porch, making things a little uncomfortable. I told her I had a good time, gave her a little kiss, and left. When I got home, I texted her, thanking her for a great night and telling her I'd like to do it again sometime.

"Glad you had fun. I had a great time too. Definitely."

The next morning, I woke up and took a piss, noticing a major discoloration on the tip of my dick. A deep blue contrasted the normally purple head. I panicked. I mean, it couldn't have been an STD showing up that quickly, could it? I didn't fuck her, but I guess you can get shit from blowjobs, right? Maybe something seeped through her panties and got to me? Maybe her panties were bleeding color or something with her wetness?

A solid 5 minutes of freaking out and staring at my cock from every angle, it finally hit me. The perfectly round, dime-sized mark looking like I dropped a bingo marker directly on my pisshole... A fucking hickey. Jesus. Wait, nope. A fucking dickey (pray that word somehow becomes a regular part of your vocabulary).

The text that night was the last I ever heard from her. No idea what happened. I texted her a few more times, sent some memes and gifs, then flat out asked her what was going on. Nothing. She was gone. Too bad too, she was so much fun. I could use head like that more often. I'm thinking at that point though, that was once in a lifetime shit.

Date #9 - Lisa the Lovely

My first girlfriend in forever, not that it started that way. At this point I was fully addicted to dating. Chasing the dragon for that fix. I was running on multiple apps and drowning in conversation. Eventually I decided that juggling more than 10 matches at a time wasn't ideal. I fucked up a lot because of it. Responding to the wrong people, asking repeat questions, and it was a mess.

In that mix, however, I matched with Lisa. Lisa was super cute, my age, tall, thick and busty. She had that sexy librarian thing going on with her glasses and big toothy smile. She was the right kind of curvy. Real thick. One or two super-size me's from falling part, but still had a flat tummy despite her ample thighs, butt, and chest.

She was fun too, we chatted for several days, but I had too many dates lined up to schedule something. Like countless others before, one day she just disappeared from the app. Gone. Profile and everything, nowhere to be found. I felt I fucked it up majorly somehow.

A couple of weeks later, I found her on another app and messaged her, 'hey stranger!'

She matched quickly, 'oh my God, I'm so glad you found me! I got overwhelmed on Hinge and deleted it, but I really regretted not giving you my number first.'

Boom, it was on. I scheduled a date right away and a couple of days later we were at my coveted beachside, rooftop place watching the sunset and slipping her favorite Pinot Noir. She was sexy. Bright yellow body suit with tight black slacks, nipples poking through the stretchy fabric in the cool air-conditioned atmosphere. We laughed and flirted, finishing the bottle, and talked about hitting the beach.

I couldn't stand it, I was so attracted to her, that when we hit the elevator, I immediately started kissing her. She was excellent. She felt like sex. Her firm thickness called to me.

Hitting the ground floor, I told her we needed to make a pit stop at my truck.

"You thought of everything!" as I pulled out a beach blanket, bottle of red wine, corkscrew, and two plastic cups.

We kicked off our shoes, walked to a darker section of the beach and laid out the blanket. I poured wine and we continued making out. She spilled her wine on her fluorescent body suit and we laughed.

"It's ok, I just bought three more!"

Perfect. They are sexy.

Rolling around on the blanket, my hardness died to be inside of her. She was a nice girl though and stopped me from getting too frisky when I unbuttoned my pants. More talking, laughing, and wine, we kissed and touched more, then she let me unbutton her pants.

I reached back under the tight fabric, grabbing mountains of her cool cheeks and rubbing myself into her.

"Oh my god, this is crazy."

"Sorry, I don't want to freak you out. We can stop. I like you and want to see you again."

"I want to see you again too."

The kissing resumed. The petting resumed. We got hot and heavy. I pushed her pants over her big ass and sat up, pulling them off into the sand. I mouthed over her body, clamping down on her tits and made my way to her robust thighs, nibbling and licking, eventually grazing my teeth over her pussy, soaking through the thin highlighter fabric. I stared up at her face, she stared back at me. I unwrapped my arm from her thigh and flicked open the three buttons on the body suit, holding her cute bald pussy back from the air.

She giggled, I dove in, licking and sucking as her fingers ran through my hair. She lifted herself up and down into me as her juices began flowing. Looking back up at her, I flicked her little clit with the tip of my tongue between her fat lips, and pushed a finger inside. Tight. Incredibly tight.

She cooed at first then pushed my head back from where I was nibbling around her perfect little pussy.

"Sorry, I need to stop."

"No, no. I'm sorry."

"This is just a lot for a first date. I haven't been with anyone in a while and this.... It's just a lot."

I felt her recoil.

"You're right, we definitely need to save something for the second date, otherwise we're going to be full on swingers by date 5" I joked.

She laughed and began buttoning herself back up. She pulled her pants on, I cleaned up our spot, and we kissed in the parking before she left.

Unfortunately, our 2^nd date plans a few weeks later were interrupted by a god damn hurricane. We texted a ton throughout, talked on the phone, and even had phone sex at night.

"Phone sex! Who has fucking phone sex?!" She mused, relaying the conversation she had about me with her friends.

The storm had passed, but her power was out so she was unsure about another date so quickly.

'I guess you could come over, but I don't know what we'd do.'

'Yeah, you're right, whatever could we possibly think to do with a bottle of wine, in the candlelit darkness. Nothing we could do to keep us entertained.'

She sent a series of laughing emojis and would later brag about that comment to her friends. The next night I went to her place.

We shared the same bottle of her favorite Pinot from that first date which I had picked up on the way and then another she had laying around. We talked on the patio for a couple of hours. She excused herself to the bathroom and I met her in the hallway, kissing her and rubbing her body.

That night it was a purple body suit and black shorts. I had them off of her in a quickness. She ran around her room lighting candles as I watched her big white, sexy tan-lined ass jiggle in the flickering light as I got naked on the bed.

I pulled my cock and she climbed on top of me, kissing my lips, nibbling down my neck, my chest, licking my nipples then biting down my stomach. She gave me perfectly serviceable head, nothing special, but enough to get the ball rolling until I pulled her back on top of me. I felt her fat pussy engulf my shaft, she ground a little and I pushed her to the side on the bed.

I buried my face in her tight little honeypot. Noticeably looser than last time - she must have been so nervous before - but still plenty grippy. I worked my finger in and out as I sucked her little clit and she pulled on my ears, clawing my scalp. She came with a breathless "yeesss" and I mounted her.

Her full, flowing body invited me right in. I pressed my cock against her little hole, slipping myself in and grabbing her thighs against my chest, slowly stroking in and out. I pushed forward on top of her, holding myself up above her as she held her knees back, allowing my cock fully into her depths.

In and out, her big tits rocked in waves up and down as I rose up to admire my work. Her thickness took me and I pounded harder and hard.

"Fuck me from behind."

"Flip over."

I kissed her and bit her lip, pulling out and watching her flip to her hands and knees in front of me, her massive ass up in the air. I drove in, grabbed huge swaths of skin right at her bikini tan lined hips and pounded. Her body rippled with ever hit and her already clutching canal, squeezed hard as she came.

"OH FUCK FUCK YEASSS!!!"

I exploded seconds later, pouring my pent-up seed from the bottom of my 'I've been fucking around with a bunch of girls and haven't busted a nut in a week' balls, she moaned, "wow I can REALLY feel that."

I collapsed in sweat onto her clammy body, squirting out of her leaking pussy and licking the salty sweat from her neck.

"I should have asked before cumming in you."

"I would have said something before if I was worried. I'm on the shot."

We cuddled naked, soaked in the humid Florida air wafting through her open windows and fresh sex, laughing that we could hear the neighbors through everyone's open windows, knowing they most certainly heard us. She invited me into the shower as I was about to fall asleep, but I declined, passing out before she even had the water on.

We woke up the next morning with my morning oak in her crack, immediately fucking in the spoon position and I tried pulling her on top. She seemed reluctant, but obliged, then began holding her stomach and tits as if she was trying to hide them from me.

"I love your body, don't hide it from me."

"Sorry, I just hate being on top. It's doggy for me every time."

That was the start of the downfall. I love cowgirl. I can see and feel everything. I'm not big on doggie. She loves doggie. It makes her feel sexy and she cums the hardest that way. And, she hates being on top.

Whatever though, she was awesome. She did live far away, but she was someone who I knew I could spend a lot of time with. She was smart, fun, sexy and I really liked her.

We got up, went to breakfast, and I drove back home - an hour-long drive.

It took almost three weeks for our schedules to align for another date. I went over to her place again and we drank and fucked just as before and it was great. We woke up the next morning and got to talking. Planning another meetup and it quickly devolved.

Our schedules sucked. Her hours, my hours, the distance. It just didn't work. It was really hard to get together. She was my girlfriend despite not really having spent that much time together or officially making it official. I shut down the apps and was happy as a clam, just waiting to see her again.

We eventually had another rendezvous, very reminiscent of the post hurricane meetup. More wine are her patio and another good frolic in the bedroom. We cuddled ourselves to sleep, waking up the next morning still holding each other. I was ready to make it official, but as we talked, we both realized it couldn't possibly go on further.

She cried and I held her for several minutes. She sniffled, wiped her eyes as she looked up to me from my chest, "I need to feel you one more time."

I spooned her and we slowly made love. I delicately caressed her and kissed her neck and ears. She reached back and held my ass, grinding herself over me. I finished and she turned to me, lightly kissing me and running her fingers through my beard. We stared into each other's eyes and kissed, lovingly touching each other.

"It's time for you to go," she said, her eyes welling in tears.

"I guess you're right."

I kissed her deeply one last time, holding her close. I hugged her, kissed her tear-soaked cheek and got up to collect my clothes. I got dressed as she laid in a ball under the covers, sniffling.

"I'm going to go," I said quietly standing over her.

She sniffed and nodded. I leaned down and kissed her forehead. "Goodbye" I whispered, turning and walking out of the room, hearing the sounds of her quietly breaking down behind me.

We texted periodically for a while, until we both faded away, and eventually, she popped up on my social media some months later. She looked happy, hanging on what looked like a really nice guy, in her profile pic. I was so happy for her. I'm so glad she found a good guy.

Date #10: Angelica the Nothing

Nothing at all special about this experience, but it was the first time in which my date looked way better in person than in her pictures. A LOT better.

She was pretty enough, very tall, and curvy. She was from Spain. Olive skin, thick brown hair, and a cute smile. I was a bit reluctant based on the mediocre conversation and pictures that weren't very impressive.

In person, everything was amplified. Her 5'10" frame held her curves perfectly. Her body looked better and her face was more than pretty, she was beautiful. Thick plump lips, pretty brown eyes, and an adorable accent. She had a funny thing with her mouth as she talked, hard to describe, but it was almost like her mouth didn't move exactly the way it should with the sounds she made. Endearing.

We had a nice date, hugged at the end, but despite my attraction to her physically, something was missing. Maybe if we had kissed it would have been different, but I was talking to too many people to bother finding out. My dance card was once again, full.