The 50-First Dates Ch. 31-40

After dinner we walked to the waterfront benches I often end up at and sat chatting. I kept looking at her; big brown eyes, freckly skin, and long straight auburn hair - there was something super sexy about her. Looking down at her ample cleavage and her cute, raspy voice didn't hurt at all either.

We discussed how she was fresh off a marriage, exploring her bisexuality, and wasn't in for anything serious. As she was talking about how I was obviously some sort of dating expert, I just started kissing her mid-sentence. She gave me ALL of her tongue immediately, but settled in to my style very quickly, going from "what the fuck is this" to "hey, she's actually a good kisser" in record time.

My hands found their way onto her massive thigh and teased up under her shirt pretty quickly. She started getting excited and rubbing me through my slacks as passerby's strolled down the walk. I had my hand almost under her bra, struggling to wrangle one of her massive tits when she broke free.

"I want to take you home with me, but that's a bad idea."

"Is it?"

"Yeah, it is."

"Why's that?"

"If we did that, we'd have sex."

"I'd imagine so."

"I've only ever been with two guys."

At 28 years old, Malorie had had exactly two relationships. Lost her virginity to her high school sweetheart, then shortly after they broke up when she was 19, met her much older husband (currently in his 50's).

"And some random guy from Hinge isn't your idea of number 3, right?"

"I'm not against the idea, but it's a first date."

"No doubt."

We hit the pause button and I switched to discussing her newfound bisexuality.

"Have you even gone out on a date with a girl yet?"

"No, you're my first date ever."

"Any prospects?"

"Actually, yes. I have a date with her tomorrow."

"Fun. Want me to come along to help you through it with my expert advice?"

She laughed, "I think I'm good."

"Ok then, you'll have to tell me all about it."

"Sounds good", she giggled.

We made out a bit more walked back to our cars, saying our goodnights and heading home. We chatted a bit before her date and late that night, she started texting me again, but I was already in bed. Circling back around the next morning, we had a fun talk about the differences between her two dating experiences.

'You're definitely a better date.'

'And a better kisser, too.'

'Maybe.'

'Pfft! You loved it.'

'I liked kissing her too.'

'Best of both worlds, I guess.'

The more we talked the more apparent it was that she was interested in both of us. Seemed like things might be falling into place for a threesome, or maybe I was just fantasizing too much. Over the next week we continued talking and planned a second date.

On the day of our date, she sent me a text asking to reschedule. No problem, happens sometimes, though I did notice she didn't offer any alternatives, which is never a good sign. Still no problem, I had no investment at all, she was just possibly a fun fling or maybe ongoing friend with benefits situation.

Another week went by and our texting was still going strong. I attempted to schedule another date, but she was wishy washy. Been here before, so I knew she was about to disappear. Interestingly enough, she didn't. She kept right on texting, sending me of a bunch of different women she claimed were all her, and continued our little flirty dance. I was rapidly losing interest so one day I confronted her.

'Not sure what's going on, but it seems like you're not interested in seeing me again.'

'It's complicated.'

'Shouldn't be. We're both looking for the same thing, there's an attraction, not sure what can be holding you back.'

'Remember Dana?'

'Your lesbian date, sure. You guys getting married?'

'LOL she's not a lesbian. She's bi. And married.'

'That's scary.'

'Why?'

'You're involved with a married woman. I'd expect you to be shocked by that.'

'I knew before I went out with her.'

'Interesting.'

'They're poly.'

'Ah and you're part of the group, huh?'

'I guess so.'

'Sounds unsure.'

'I am, but we're not doing labels.'

'Ok, so they don't want you to see anyone else?'

'They don't care, but it's weird for me. I feel like I'd be cheating.'

'Things are that serious?'

'I don't know. I thought I could do the casual thing, but I'm getting feelings for them. And then you're great too and I don't want to fuck that up.'

'Woah, nothing to fuck up here. We went out one time. We had a good time, but we talked about not being serious or exclusive.'

'I'm not sure I can do that.'

I didn't need to hear anymore. She wasn't cut out for the type of sexuationship I was interested in with her, so I told her she should explore things with her new couple and not to worry about me. It was odd, she almost seemed to be upset like I was breaking up with her. She didn't really say anything, but her messages became short pretty quick and when I wished her luck and said goodbye, I never got a response - like she was hurt.

Date #34: Jen the Mom

I matched with Jen and the conversation was solid enough. Combined with a very pretty face and nice curvy body, I was quick to set up the date. She was late 30's, blond hair, blue eyes, maybe 5'4" and had great thickness.

When I met up with her, I was not disappointed. Tight jeans, tight pink top with a hint of midriff, and jean jacket that didn't quite match the color of her light jeans. She was very pretty, bubbly, and her smile really drew me in.

I knew she was a mom based on her profile, but our conversation wasn't too deep leading to the date at a local attraction. I found out pretty quickly, she wasn't just a mom, she was a MOM.

Still having a preference for childless women, I never really had a boundary as to how many, how hold, or how involved a woman was with her children. I wasn't looking for anything serious at that point, so it largely didn't matter, but with Jen I really questioned it.

Jen had 5 kids. 4 boys and 1 girl, ranging in age from 22 to 4. Listening to her describe her life over our fajitas I knew it wasn't going anywhere. No big deal, it didn't need to, but the more she talked the less attracted to her I was. As any good mom should, her life absolutely revolved around her kids.

It was really all she talked about. All she had to say. She had no hobbies or interests outside of being a mom and from the sounds of it, she was a great one. Involved in every club, sport, hobby, and whatever else her kids were in to. Part of this was endearing, but as I started asking questions about how she finds time to date and what she is looking for it was abundantly clear I just wouldn't be interested.

Our date was the first time she had gone out in months. Months. No drinks with friends, no dates, no time at all for herself. Full-time mom. Quite respectable, but again, it wouldn't work for me.

The kicker was when I broached the subject of what she was looking for, she admitted she wanted a father figure for her kids. I wasn't signing up for that and it really changed how I filtered during discussions on the apps. Moms are cool, dating a mom is fine, but the freedom of a childless woman is way, way easier. She can move around my schedule and not the other way around.

Despite being fun and us having a great time, I didn't even go for a goodnight kiss. I simply gave her a hug and sent her on her way. She never texted me; I never texted her. She definitely got the feeling there at the end that I wasn't a good fit for her.

Date #35: Wanda the Firecracker

This is another one I took a little chance on. Wanda was older than me, 44, and looked pretty cute on her profile. She looked amazing for her age on the screen, but photos can be very, very tricky. She was originally from Puerto Rico, moved here several years back after her partnership failed, and she wanted a change.

On her profile, she had a few full body pictures that told me she had curves, but she might have been a little fat. She had big green eyes, multi-colored hair, and that pale freckly skin I love. She didn't fully smile in her pictures, which could mean she has bad teeth or maybe just a little crooked like I like. If her pictures held up, she could be a lot of fun, but I went in with pretty low expectations.

When she pulled up, she looked ok through her window. Then she got out. Holy shit! Wow! Wanda was HOT.

Not a bit fat. 4'11" big D cups, small waist, nice hips and an ass that can only be described as a booty. She smiled big, sporting near perfect teeth with just a little bit of crookedness which drove me wild. Her hair, while blue, purple, and green also showed her natural strawberry blonde. Absolute smoke show.

We ate dinner and had a good conversation despite the slight language barrier. I had to repeat myself a few times and she searched for words here and there, but overall, it went pretty smoothly. She liked a lot of things I liked from movies to music to drinks and food. She was a "down for anything" chick which is important for me. Picky eaters and non-adventurous women are a huge turn off.

After dinner we walked through the park and around a lake, talking and being playful. She wanted to sit on some of the benches lakeside and the conversation continued. She had a little bit of an edge to her, though I was still surprised when she brought up sex.

"Ok Mr. Jack, what do you like for sex?"

I laughed, "what do you mean?"

"Do you like rough sex?"

"A little bit, depends on what you mean by rough."

"Tie me up and spank me."

"I can be down for that. As long as you don't want me to really hurt you."

"Choking?"

"I like to choke."

"Hold me rough?"

"You mean, like this?"

I threw my arm around her waist and yanked her petite body up onto my lap, biting hard on her neck.

She giggled, "OH Mr. Jack, you like it."

"I do."

She kissed me hard, repositioning herself to full straddle me. She was a solid kisser, swirling her tongue around my mouth while pulling my ears to force my face into hers. My hands held her narrow waist, working my fingers down her jeans and up her shirt.

Just as I found the underside of her bra, she broke free.

"Let's keep walking."

Half hard in my shorts, we made our way around the lake and stopped at a bar. We drank a few beers, made friends with a couple at the bar, and I just marveled in how sexy she was. The accent, her innocent look, that pretty face, the incredible body. I had thoughts in my mind that she was someone I definitely wanted to keep around for a while.

A few rounds deep, it was getting late and we left just before last call. She put my arm over her shoulder and held me as we walked to our cars. We made out again and I got a couple of good squeezes on her supple ass, overflowing handfuls of perfection. Exactly the right size, shape, and consistency for me. She made me hard in seconds.

"Mr. Jack, you're excited" she teased.

"What can I say, you're damn sexy."

She giggled, "I like what I do for you."

Giving me a quick peck on the lips, and playfully pushing down my rock-hard member, she opened her door and sat down.

"Another date?"

"Absolutely" I groaned, thinking of my dick dripping in my shorts.

I leaned in and kissed her, got in my truck and we both left.

She was initiating texts a lot that next week as we planned our second date. My favorite oyster spot, then a little dive-bar up the road for drinks. I figured I was well on my way to a little girlfriend.

She showed up looking hot again and ate an amazing number of oysters for a woman her size. We downed three buckets and two pitchers before heading to the next stop. Placing ourselves on the patio, we ordered a couple of beers and she talked like we were a couple.

We cuddled as the wind picked up and the rain started misting, drinking our beers, and discussing her plans to see her favorite band in concert a few weeks later. I liked her, she was fun, and so damn sexy.

We closed that place down and were the last ones there. The rain had subsided and we made our way off the patio after paying the tab and made out on the side of the building. Things got hot and heavy pretty quick.

My hands found their way down the back of her pants and into her silky panties, gripping wondrous handfuls of her perfect ass. I licked and nibbled her neck, bit hard on her clavicle as she clawed the back of my head.

"MMmmm Mr. Jack."

She licked my ear and bit my lobe roughly, I pulled both hands from her pants and slapped hard on her ass, pressing my diamond hard cock against her stomach. I teased my fingers around the top of her pants, playing in and out of the top of her panties.

"They're soft."

"I like them."

"It's soft down there too."

Both of her hands fondled my cock through my shorts as my fingers probed their way deeper into her panties, feeling the soft trimmed hair just above her pussy.

"It's hard down there" I grinned.

"I see that."

Just as my fingers touched to top of her moistened slit, she pushed my chest back.

"Not here."

"Come back to my place?"

"It's late."

"It is. So, another date?"

"Si."

I walked her back to her car and we kissed a little more. We made plans for her to my place next time to watch a movie. Netflix and chill. Great!

I was a little smitten to be honest. She was physically damn close to my ideal. She was fun, drank and ate like an actual adult (rare with women), and liked smoking pot. She was a wonderful option for a time for sure.

Just like before, she was still initiating texting more than I was and I had a really good feeling about her. I REALLY wanted to fuck her. We continued to talk about movie options for our next "date" and things seemed to be going along swimmingly.

'I don't think I should come over tomorrow.'

'Why, what's wrong?'

'I don't want to lead you on. It doesn't feel right.'

'If things moved too fast, that's not a problem. We can slow it down. I'll be on my best behavior, or we could always just go do something else. Whatever makes you comfortable.'

'I don't feel a spark.'

'Oh, ok.'

'If you want, I'll take you out as friends.'

'Friends make out, right?'

'LOL, no they don't.'

'Ok, well I'm in if we can make out.'

'I don't think so.'

'Ok then, no problem. I'm honestly too attracted to you to just be friends cause I'm always going to be wanting to make out with you and bite you and play with where it's soft.'

'LOL'

'If you want to keep it casual, I'm open to that too.'

'No, that's not for me Mr Jack.'

A few more messages back and forth and it was over. She continued messaging me for a few weeks, trying to get me to hang out while also denying my advances. Eventually I just stopped responding. My time is full of women who actually want to fuck me, so I don't waste my time on those who don't.

Date #36: Laurie the Box

Another risk, another 'fatfish.'

Laurie was a cutie and super fun. She had a tomboyish nature, huge tits, and loved to drink. We matched and her profile hinted at her being maybe a little chubby, but nothing extreme. And the truth is, her body wasn't extreme outside of her giant tits.

It was pouring when we met and the second she got out of the car my heart sank. Standing there holding the umbrella over her, I knew immediately I wasn't interested, but there I was, might as well make the best of it.

As we walked through the rain, huddled under the umbrella, I got to thinking that maybe another 'friend' wouldn't be a bad option there. She wasn't unattractive. Plus, Friend with benefits Lucy was still with her ex and I was still riled up from Wanda the night before.

I really, really wanted sex and Laurie might have been fun.

She was average height, long blond hair, super cute face, those monster tatas, and a square body. No hips, no ass, just torso. A slightly chubby torso. As an ass man, hips and butt rule and unfortunately, she had neither.

We sat at the bar, ate, and drank wine. Conversation was effortless, but I had to keep my eye from wondering a lot on the super-hot bartender who was definitely more friendly with me than she was with Laurie.

"I think she likes you."

"Should I hit on her?"

"Yeah, go for it!"

"I think that'd be bad form on a date."

"You think?"

"I don't know, now I'm questioning it."

"I guess that depends on if you want a second date or not."

"Honestly, I've been thinking about that. You're super cool, but I'm not feeling a connection. That doesn't mean I don't find you attractive. Just getting more of a friend vibe."

That wasn't totally a lie. The more we talked and the more I stared at her cleavage, the more attractive I found her. I'm sure the two bottles of wine we went through weren't hurting either.

"Same."

"Ok, good."

We cheers'ed and finished our glasses.

"So, are you going to hit on her?"

"No, it's still bad form."

"I'd kind of enjoy watching you do it."

"That's a lot of pressure."

"Don't work well under pressure?"

"Do you?"

"Try me."

"Let's make out."

"Right here?"

"Nah, I'm a fucking gentleman. Let's do it in the parking lot."

"Romantic."

"I think we've established romance is off the table."

"Oh, so 'friend vibe' means you just want to hook up."

"Not a hookup guy."

"Just a make out guy."

"Not juuuuuuust a make out guy. I wouldn't mind an ongoing friend situation."

"Ah, I see."

"If that's not your thing, I understand."

"I could work with that."

We made our way through the parking lot in the light drizzle, stopping at her car so I could see her off.

"Let's test to see if we even want to try the friends thing."

Grabbing around her waist, I pulled her in close, those giant pillows smashed against me, and planted a kiss on her. Good, aggressive kisser. Her arms around my neck, slowly released and ran down my shoulders and arms, then back up around my neck. I could tell she'd be good in bed.

"I can definitely work with that" she grinned.

"I think I can too."

We texted a few days and then she was gone. I think she was just playing along with being ok with a casual relationship and not wanting more from me. Her texting was very friendly, but had a tinge of "looking for more" and when she started to fade, I just let her go.

Date #37: Julia the Strange

Julia was another eastern bloc woman, single mom, mid-30's, very tall and lean, but with quite large tits all stuffed into a skin tight black full-length dress on our date. She looked like she could have been a model as a younger woman, but had lived some hard years. Still beautiful, but very much looking her age.

I actually couldn't pronounce her actual name, but she will forever be Julia simply because it's close enough. Speaking of close enough, her profile listed her at 5'7", but when I met her in the parking lot for our date, she was easily pushing 6'. After double-checking to see if she was in heels, I made a joke as our conversation kicked in and she said she thought the profile said 5'9" because "that's what my license says." I chuckled, telling her she needed to remeasure.

Overall, the date was a little laborious. She wasn't a big talker, the restaurant I chose was basically a giant treehouse in which they had a live band that wasn't listed on their website, making the small talk a struggle. It didn't matter though, I turned on the charm and stared into her crystal blue eyes and wondered what kissing her plump lips was going to be like at the end.