The 50-First Dates Ch. 41-50

"Oooo candles!"

I followed her in and she immediately began stripping for me. The old t-shirt came off and her big, plump perky tits fell to the sides. She squeezed them together and lifted them to her face, licking back and forth between her nipples as she gyrated her hips. I sat on the bed as she twirled around, bending over at the hips and popped her back, shaking her ass in my face.

She squealed and giggled as I slapped hard on her ass. Dropping down to the floor, she twisted as she rose up and ran her thumbs around the top of her pants, rocking her hips back and forth as she bent back over and pulled them down.

"I'm so fucking wet" she moaned as she reached between her thick thighs and rubbed her pussy, making macaroni sounds as I played with myself. Sauntering over as I pulled my shirt off, she poked my chest, pushing me back onto the bed. She reached down, pulled my waistband and rubbed her massive chest up and down over me. I lifted so she could pull my shorts off and she climbed on top.

"Mmm, daddy, I want to feel that dick."

Sorry to break the tension here, but I must confess. I hate that daddy shit. Madison was so sexy though; I wasn't about to stop her from doing anything I she wanted. She was pure sex. Endless plush curves, buttery smooth skin. The perfect amount of meat on every part of her body for me.

She mounted me, rubbing her freshy shaved pussy up and down my cock. I wanted to go in raw so bad, but something told me it wasn't a good idea, so mid-kiss, I flipped us over and reached over her head to the nightstand to grab a condom.

"Mmm... good boy."

With the condom pinched between my teeth, I stared down at her and I couldn't help but touch every part of her I could reach. I played with her big tits, squeezing their young firmness and tweaking her nipples. I lightly touched down her stomach, pausing to grab a handful of her little belly and running down between her legs and pushing her soft thighs back, my cock teasing her opening inadvertently.

Slipping the jimmy on, I rubbed it up and down her glistening pussy, then pushed into her tight hole, nearly cumming instantly. She was perfect for sex. Every inch of her felt perfect, inside and out. She held her knees back as I hovered over her, drilling that little twat hard and fast. I couldn't help myself, starting to cum not even 30 seconds into it.

I paused, trying to hold back.

"Did you finish?"

"I'm trying not to."

"it's ok, you can cum."

"Not yet."

A little reset was enough for me to keep going, but it didn't last long. Another minute maybe, and I filled the bag with body pressed against her, wishing she could wrap my enter body with hers.

"Wow, that was quick."

"Not as quick as my last boyfriend. You're good at this."

"You have no idea yet," I laughed.

We got up, went out to the living room and actually started watching a movie, cuddled up on my big recliner. As with earlier in the evening, her lack of maturity surfaced. Her comments and jokes were a little annoying, but her naked body made everything ok. Maybe a half hour later, my caresses over her perfect skin brought junior back to attention.

"Round two?" I teased.

"Definitely!"

We got up and went right back to the bedroom, picking up exactly where we left off. No foreplay, just another condom on with a quickness and reassuming our final position. This time, however, my body was ready.

Splish splash, I tore her up. Her moans turned to screams, alternating between my name and that "daddy" crap. I didn't care, I was a wrecking machine of sex. Pure destruction of everything I loved about touching a woman. She clawed my back as I ravaged her into exhaustion.

"I want on top so I can cum again."

Absofuckinglutely.

I rolled to my back and she followed on top, one knee in the mattress and the other up in the air over me. She directed my meat around her opening as she pushed her tits together and teased herself over me.

"Oooohhhh" she whispered as she guided me in and sat down fully.

She bucked up and down as I held up her bouncing tits and roughly swam each hand up and down her body individually, grabbing handfuls of sweetness everywhere along the way. Tight, young, thick, firm, sexy.

The more she got into it the more inhabited became and the more her dripping wetness coated my pelvis. That tight little pussy and all her creamy wetness caused something I've never experienced before. Out of nowhere, I realized the condom was gone and I was fucking her raw.

At that point, it was done, so I didn't even hesitate to continue. I just knew I couldn't cum inside of her and she very specifically didn't want me to.

She had another orgasm and a request, "fuck me from behind, daddy."

As you wish.

She flopped down next to me and got up on all fours. I moved behind her and began massaging her hot pussy juice on my straining cock. Sliding right in, I grabbed big handfuls of her hips and ass pounding with all my might, the headboard ricocheting against the wall.

"Yeah, fuck me daddy! Pull my hair!"

I wrapped a huge handful of her thick hair into my fist and pulled her really hard into me, folding her backwards.

"Yeah daddy! I'm cumming hard daddy! Fuck me just like that daddy!"

Slap slap slap slap slap slap

"You like that fat cock baby? You like it?"

"I love it daddy, I love it!"

"Fuck yeah you love it! You love that hard dick!"

"Yeah! Yeah! Yeah!"

"You ready for me to cum? You ready to feel it?!"

"Cum for me daddy! Cum!"

"Fuck yeah, I'm gonna cum!"

Not a goddamn thought in mind except for emptying my balls, and empty them I did. Yanking her head back by the hair and tearing a chunk out of her hip with my other hand, I buried myself deep against her luscious ass without a care in the world, pumping my load deep within her.

"Ohhhh daddy..."

A split second later I realized what happened. Fuck. God damnit.

"That felt really good."

"That's because the condom slipped off."

"What?!"

"Yeah, sorry, I realized it, but I couldn't stop."

"Have you been tested?"

"I do, regularly."

"Good."

"How about you?"

"I did because my last boyfriend cheated on me."

"So, we're good?"

"As long as I'm not pregnant."

"Honestly, it felt like a dry load."

"Dry load?"

"Yeah, when I came earlier, I think I dumped it all. Didn't feel like there was anything left."

"I guess we'll find out."

"I hope not."

Madison didn't stick around for anything more. We looked through the tossed bedding for the condom, unable to find it until she went to pee and felt it coming out. She fished it out and tossed it into trash, threw on her clothes and left with a quickness, leaving me naked in my bed.

She didn't seem weird about anything, but I made a point to follow up the next day to be sure. She was fine, just wanted to get home because it was late and she had to work in the morning - the same thing she said on her way out. I wasn't sure that was real, but I went with because frankly there wasn't a damn thing I could do about it anyway.

All was normal and we texted the same for a few weeks. Eventually, she disappeared a week after getting her period and confirming that indeed, she hadn't gotten pregnant. I think she was a little turned off by the fact that I told her I didn't like being called "daddy", even though she seemed to take it in stride. Too bad too, because she had top tier friend with benefits written all over her. Fuck, I loved her body.

Date #43: Bree the Buddy

Bree wasn't my buddy, but after matching with her on an app and talking to her a bit, we figured out that her BFF is a mutual friend. She was tons of fun and attractive, but not really my type.

Her stats would make anyone raise an eyebrow, but for me, I'm simply not a tit guy and she was ALL tits. Ok, so she had a booty too, but the star of the show on her 5' frame were absolute monstrous jugs, bigger than your head. She had no problem flaunting them either.

We talked for about a week before we could schedule our date and, in the meantime, our friend provided her with glowing reviews. I don't need help making women feel comfortable and putting a good foot forward, but of course I appreciate having any leg up I can get.

The banter was top notch and conversation was easy, so I knew the date would be a good time. As expected, it was, even though she had a dead battery and showed up almost 40 minutes late.

She looked good though, cute with her little glasses and long dark hair. Massive cleavage tempted my gaze more than any mortal man could resist and walking to the table at the fondue place, the assets looked pretty ripe in her jeans too.

We joked about her allergies, had a little scare by some unknown ingredient causing her to get red and blotchy for a good 15 minutes, and it seemed like things were going really well. I generally don't get into it on the first date, but before we closed down the restaurant, we were making plans for another date.

I walked her to her car, she was noticeably cold, so I opened my jacket and invited her in for a hug and cuddle. That turned to making out in an instant and she laughed, "I'm SO glad you're a good kisser."

We shared a chuckle or two over bad first kisses and how that's almost always a good indication of overall bedroom performance, made out a little more, and called it a night. I liked her and it was easy, so I thought maybe it could go somewhere.

It didn't.

We chatted more leading up to our next rendezvous over the following days, but I felt her slowly fading. She acknowledged it before I could, apologizing saying she was busy and did pick up the pace with comms for the next day or two. On the eve of our 2^nd date, she was gone. A ghost. No response to my normal 'good morning' text. No response to my follow up meme that evening. Nothing ever again.

It's funny, that sort of shit happens all of the time in this modern dating environment, but I really didn't expect it here considering we have that mutual friend. Oh well, I always have other options, so no huge loss, but I do think it would be funny to run into her at a party or something sometime and give her some shit for it.

Date #44 - Ada the Influencer

The award for most interesting career out of any woman I've dated so far definitely goes to Ada and frankly, that's the only reason I'm mentioning her. She was a social media influencer, doing makeup tutorials and hocking various products. She started off a photographer and videographer, and by working with various people in media parlayed that into a good career online.

Now, you'd think because of her job title that she would be the most beautiful woman you've ever seen, but you'd be wrong. She wasn't unattractive, but she took a god damn good picture (go figure) and apparently wore all the makeup she markets at all times. Mid-30's, slight Russian accent, 5'7" or 5'8", blond hair, blue eyes, and what I can best describe as a frumpy body. She had curves in the right places, but also some in the wrong places too. She wasn't horrible to look at, but certainly wasn't for me - especially because I had just met another woman who I was wildly attracted to. We had a nice dinner, a couple of drinks, and when I walked her to her car at the end, I simply just wished her luck on her dating adventures.

Date #45 - Mary the Decisive

Mary is a cutie. She was also incredibly indecisive when it comes to what we are and what we're doing. I'd make her my girlfriend, but she wants kids and I don't. We had a great chemistry off the bat and some of the best banter out of any women I've ever talked to. She's just a ton of fun and, well, sexy as all get out.

36, 5'10" with a bit of curves. Nice perky butt that's small on her, but more than a handful for any man's hands. And, while I'm not a boob guy, she's got big'uns. Long legs, pretty blue eyes, nice smile, very funny and is very, very smart. An entrepreneur she owns a couple of salons and in a funny twist, one of my favorite breakfast spots in town. Mary was girlfriend material.

The story arc of Mary ebbs and flows in and out of us becoming a couple, becoming platonic friends, and just being friends with benefits. At first, she was a match like any other. Good convo, things aligned in terms of lifestyle, super flirty, but then the subject of kids entered the fray and neither of us were going to compromise.

At that point we hadn't actually met yet, so she started immediately playing matchmaker with one of her single friends.

'She's a redhead, tall, nice body, has a couple of kids, but isn't currently dating. I'll see if she's interested.'

'This is the most interested online dating experience I've ever had. We've gone from let's be a couple, to maybe let's fuck, to "I'm going to hook you up with my friends" lol'

'I never said we would fuck! WTF!'

'No, but you thought it.'

'Maybe.'

Unfortunately, or fortunately, I didn't find her friend especially attractive, so after brief awkward conversation we resumed our flirting. She insisted over and over again that she could not do anything casually, but continued to feed into our attraction. After several days of near constant contact, she agreed to go out on a date.

I chose one of my go-to places - hibachi and sushi, with an arcade right next door. There was a small miscommunication on the start time, so I ended up sitting in the parking lot waiting for her for almost 40 minutes. Definitely worth the wait. Greeting her, I was instantly attracted as she was rocking 3" heels and towered over me. That, in and of itself, wasn't really a turn on. However, taller women usually wear flats unless they're out with a really tall guy, so I really liked her confidence.

We ate sushi, shared a bottle of wine, and flirted our asses off. From there, we hopped over to the arcade, had a couple more drinks and played games until they closed. As usual with all my arcade dates, I kicked her ass all over the place and things got very flirty as we went. When all the games shut down and the staff started cleaning up, I walked her to her car.

The flirting was reaching peak levels as we talked and she leaned up against her car, both of us waiting to see where it was going to go. Of course, I knew exactly where it was going.

"I'm going to kiss you now."

Her eyes went wide and she giggled, "are you now?"

"Yep."

I reached out and ran my hand around the back of her neck as I stepped in and gave her a sweet little kiss. She smiled. I took my other hand from her hip and held her face with both hands, kissing her harder with a little tongue.

"That was really nice."

"It was."

"I like how you just told me you were going to kiss me."

"I knew if I didn't, you wouldn't stop talking long enough for me to go for it."

"You're a talker too."

"Not right now, I'm not"

I slipped my fingers in her belt loops and pulled her into me, immediately swirling my tongue around in her mouth as her arms wrapped around my neck. We made out for a few minutes and I rubbed up and down her back, racked my fingers over her outer thighs, and teased up under her shirt to play with the top of her jeans.

Enjoying that progress and noting it was already later than she wanted to stay out, I ended it with another little kiss, put her into her car, and went on my way. We texted a bit more that night and then continued with a lot of communication the following week. Top tier banter and flirting - I was really beginning to like her, but I knew we couldn't get past the kid thing.

We had a lot of conversations about that. It was ongoing. She'd get hot for me, then ask me about having more kids and I'd respond as I always did, which would prompt her to revisit the idea of a casual thing only to back off of it, and me finally reiterating that it was her choice and I was good with either way our "relationship" went. I did want her as a girlfriend, but I also didn't want to be the reason someone would give up their dream of children or waste their time with me and missing out on someone else who could give her that.

It was tough though. I did really like her and she, was VERY into me. Reluctantly she agreed to another date, but cancelled the next day.

'You're a super nice guy and I have a lot of fun with you, but I can't get over the kid thing. I started talking to someone that I align with more in that way, so I'm going to see where that goes.'

'No worries. I hope he gives you everything you're looking for and I really appreciate you being up front with me like this. If things don't work out, you know how to find me.'

'I'll probably be calling you in about a month.'

'Can't wait.'

It was a little over two weeks, not a month.

'What have you been up to?'

'Oh, met some girl who wanted kids, fell in love, got my heart broken, rebounded with 11 hookers and a midget, then found my soulmate, got married, had 14 children, watched her slowly die of cancer... the usual... what have you been up to?'

'a midget?'

'THAT'S WHAT YOU GOT FROM THAT????'

'lol'

Just like that, we were back in action, picking up right where we left off and repeating the same damn conversation about "should we" or "shouldn't we" and "what are we" and "where is this going?" She was really in her head about me, which scared me a little bit because I felt like she might compromise and regret it, or go physical and get too emotionally invested. I was totally honest with her, never changed a damn thing with my stance, and ultimately told her it was casual or nothing. I would feel terrible being responsible for her regretting not having kids or wasting her time with me if there's a chance, she could have gotten that with someone else.

Another week of back and forth, we were on another date.

We met in the parking garage in a trendy area I loved to take dates. Lots of little restaurants around, a couple late night bars, and a small lake that was nice to walk around. We opted for Mexican, margaritas and carnitas, continuing to build upon our strong attraction. God damnit she looked hot.

Skin tight, short, sleeveless pastel dress in the unseasonably warm weather, highlighting her curves and catching the eye of ever guy she walked by. After dinner we walked around the lake and went to a basement bar for another drink. Getting more comfortable in a dark corner booth, our favorite subject came up again as my hand was rubbing just past her knee on her inner thigh. Kids, casual, the same.

At this point we were both on repeat. Over all of it again, exactly the same. No resolution, but we made out a bunch anyway.

I walked her back to her car and our kissing turned to light petting. I couldn't keep my hands off her tight body and soft ass. She commented about how she'd never got so frisky in public, let alone a well-lit parking garage with the occasional person walking around. I checked in to make sure she was comfortable and she responded by kissing me harder.

Things progressed. I rubbed all over her body. Up and down her taut sides, over her tight stomach, up to cup her big firm tits, eventually I hiked her dress up from her mid-thigh, reached far back and felt onto her bare ass, noting she wasn't wearing a thong.

"I don't like thongs."

"Fuck yes, neither do I. These cheekies are seeeeex-y."

"They're just plain."

"Let me see."

She nods sheepishly.

I lifted her dress up in the front to expose the beige silk, seamless panties in the front.

"Oooo, these are nice," I whisper as I ran the back of my fingers up and down her warmth.

"They're just basic."

"Basically hot."

I pressed between her milky thighs, rubbing under and touching a bit of wetness.