The 50-First Dates Ch. 41-50

"Is this ok?"

"I'm not stopping you."

"Well, then."

I pull her dress up to her hips, and plunge my hand down the front of her panties, cupping her entire bald snatch in my hands, rubbing the entire area firmly.

"Ohhhh."

Her little moan gave me permission to slide my middle finger between her plump lips.

"Mmmhmmm, you have a nice little pussy."

She rolled her head back as a circled her sopping opening, looking around to make sure nobody was coming. I licked and bit on her neck as I pushed the front of her panties down with my wrist and slipped my finger up inside of her, immediately rubbing her G-spot. She grabbed my face and kissed me.

With her height, tight panties, and kissing, I couldn't keep the right angle to stay inside so I pulled my dripping finger out and rubbed her entire pussy, finding the clit and lightly flicking my finger over it.

"God damn, Jack."

"It's bad huh?"

"You know it's not bad."

"I know," I wink.

"I'm so fucking horny now."

"I'm thinking about stuffing you into the back of your car right now."

I pull my hand from her underwear and tug her dress back down.

"I'm not doing that."

"It was a joke."

"I know."

"Though..."

"Stop!" she giggled.

"I am. That's enough for you for tonight. Give you something to think about when you get home."

"Good thing I just got new batteries."

"Don't forget to send pics."

"I'm not doing that either."

"TEASE!"

We shared a few more giggles and kisses, then left, both wanting more. For the next few days, we had that same conversation over and over again. I attempted to set up another date, but she was reluctant. We both knew it was only a matter of time before we were fucking.

Over the next week we continued chatting, then she pulled the rug out again. Want's kids, can't do friends with benefits, wants to distance, and all that. I was disappointed because I had a lot of fun with her, but I respect it at the same time.

Of course, just as before, she folded pretty quick and started messaging me consistently right away. I didn't push anything, but eventually about a week later, she was trying to set up another date. We both actually had dates planned, but she was going to cancel hers. When I told her about mine, she offered to go out for drinks after our dates.

On the eve of our rendezvous, I had another date that went very well. VERY well. She knew I was on a date and sent me a funny message, 'I hope you're having a really bad date.' I saw it at 6am the next morning and replied with a "prepare yourself for disappointment" gif.

We chatted, she fished and found out more than she cared to and once again, backed off while leaving the door open a bit. She seemed upset, but played it off like she wasn't.

'Look, if I thought there was any chance of anything between us, I wouldn't even be dating. I like you. You're fun. You're smart. You're hot. Doesn't seem like we fit long term and you're not interested in short term or casual, so I thought we were DOA. I'm sorry if I've in any way upset you.'

'I know. The kid thing, the casual thing, I just can't. Sucks because maybe it could be something otherwise.'

'Agreed.'

We chatted a bit more here and there, but then she finally got the distance she had been promising for more than a month. Truth is though, I know she'll be back. We have that spark everyone's always looking for and when you have it, especially for women, it's very hard to snuff out.

Date #46 - Suzanne the Separated

What the fuck was I thinking? What a total waste of time.

Ok, I know exactly what I was thinking. Having Tanya lined up for weekly sex, Madison appeared to be heading in that direction, and Mary being on the fence, I had the idea to have four fuck buddies lined up into a rotation. Sounds good in theory, but it was a really stupid idea.

First, at this point in the journey I was getting pretty well worn out from dating. I had taken breaks before and it was time to do it again, but I got greedy and lost touch of what I actually wanted. In fact, I really didn't know what I wanted, I was just in perpetual motion. The ups and downs, more lows than highs, there was nothing fulfilling and I sunk into it instead of pulling myself out. Looking back, I realize I was depressed. All of those fun dates that go nowhere left me feeling empty. Right at a particularly low evening, I opened the app and there's Suzanne.

Suzanne was early 40's, pretty plain looking, terrible kinky hair with no style, but she was cute enough, looked to have nice tits, and was short with a big butt like I like. No kids, recently separated, not really sure what she was looking for. In my experience, that means, "looking to get dicked down."

I threw caution to the wind as I sometimes do and struck up a conversation. Within four messages I had her agreeing to a date the next day. We met at a decent restaurant on her side of town where I found out I was her first date in more than 20 years. Actually, based on how she described her "romance" with her soon to be husband, it was her first date ever.

As I always do, I met her in the parking lot and my gut twisted as she got out of her car. She had some light filters on her pictures, which were apparently, pretty heavy filters. She wasn't ugly per se, but she was way more plain and older looking than her pictures. Same terrible hair, still pretty nice tits, but probably 40 more pounds than her pictures represented.

We had a nice dinner, she thanked me for showing her what a good date looked like, and I wished her luck on her future dates, ending it with a quick hug and me shaking my head all the way home. Thankfully Tayna was still up as it was pretty early and she came over for a little fun - including making fun of me for trying to be such a horndog. "You and your rotations."

I know I've said it 100 times before, but now I meant it - No more risks. Well, no more big risks. Not taking chances like that ever again. Little risks. Hot body with a questionable face, ok. Beautiful face with a questionable body, fine. Unsure about one or the other because of filters and angles? Nope. Stay home and jerk off or watch shitty movies.

The burnout was real. I dropped my number to a few matches on the apps and deleted my profile, only keeping one going that I had a paid subscription to, which was set to expire in the next couple of weeks. The plan was just to ride out everything in the queue and take a nice, long break again regardless of where things were at with anyone.

Date #47 - Lacy the Plain

I wasn't too excited to meet Lacy. She is early 40's with a litter of kids and frankly, kind of plain looking not unlike Suzanne. She was cute and looked to have a nice body, but she didn't exactly scream "beauty." I know, I know, on the cusp of my last plain Jane, you may be asking why I matched her to begin with, but I already had her lined up before I met Suzanne. In fact, I took her out the day after my date with Suzanne. I wasn't too excited and had really low expectations.

I was wrong. Pleasantly surprised.

I met her outside of the restaurant per her request and she was pretty damn hot. Long thick dark hair, medium height and a sexy athletic frame with just a little bit of thickness. No makeup, but looking great for her 45 years. She wasn't quite a head turner, but she was still very attractive in person. Not to mention, her black lacy long sleeve shirt and tight jeans had me checking out the goods as we were seated at our table for sushi. The goods were great.

The conversation was a little labored at first, but we fell into a groove pretty quickly and her dark blue eyes and pretty smile really sucked me in. We discussed the horrors of dating, past relationships, and all that just as I do on 99% of my dates. It was all good.

The subject of religion came up and she acknowledged she was looking at someone who "has faith, but doesn't go to church every Sunday... or any Sunday." As we delved into my agnosticism, it was obvious I was not what she was looking for. I asked, and she confirmed, it was a dealbreaker.

Lacy and Suzanne back-to-back gave me a good reminder that sometimes the surprises are good. She was smart and plenty attractive enough to be girlfriend material, but with a super high standard swipe game, she would have been missed. The contrast between Suzanne and Lacy was a catalyst for much more careful swiping - as if my countless prior dates weren't enough. I think at this point I was truly worn down and exhausted which is why these two particular dates stamped the need for a more thoughtful process.

Date #48 - Olga the Patient

Olga was a Ukrainian woman with a ton of patience. We matched on one app, but I had too many convos going so I never even sent her a message. A couple of weeks later, she liked a picture on another app so I matched with her again.

She was very quick to set up a video call to verify a base level of attraction and while pretty enough, she wasn't exactly someone I was getting excited about. 38, tall and curvy, blond hair, blue eyes, and a pretty smile. She was definitely cute, but her face looked fat and her body pictures seemed like she might be hiding something.

We texted for weeks and I kept delaying meeting her by filling up my dance card with a bunch of other dates. She took it all in stride, but did tease me a few times about having "all these dates." Finally, after a little more than a month of us first matching, I scheduled a date with her.

It was a weekday and just as I was getting ready to leave, I got a text from a friend having a potential medical emergency and asking if I could watch her kids. I headed over there and, on my way, I gave Olga a call letting her know I might be late or have to cancel, which had to feel to her like a blowoff. Luckily, it ended up being a false alarm, so I headed to the date after giving her a quick call - only ending up about 5 minutes later than I originally scheduled.

Unfortunately, she was a bit further away so she didn't get there until about 20 minutes later. She pulled in to the spot right next to me and I got out to greet her. I was both right and wrong about her.

In person, her face was quite pretty. The roundness and her thick cheeks weren't as noticeable and her eyes had a real sparkle when she smiled. On the other hand, she was definitely bigger than her pictures lead on. Not a bad body by any means, but a little too much for my liking.

Over dinner we went through all the standard motions and I really wasn't catching a vibe with her. She was a little too milquetoast for me and even though she wouldn't say it, I was definitely too wild for her. In fact, despite mentioning that she does drink, she only had a water at dinner. I had two pints.

I opened the flood gates of honesty and gave her way too much information about myself, thinking that would turn her off, but it did the opposite. She loved my wild stories. She loved hearing about my crazy dating life. She didn't bat an eye at my lifelong experimental drug use.

If there's one thing, I am God damn good at, it's knowing when a woman wants to kiss me. I can always tell. As we wrapped up dinner, I was really getting that vibe from her. I thought about putting it out there that something more casual was on the table, but I thought about my "rotation" talk with Tanya and decided against it. I walked her to her car, gave her a hug which was made super awkward because she was absolutely set up to kiss me, and wished her luck in the future.

Date #49 - Annie the Snack

Annie is fun-sized. Late 30's, no kids, 5'1", reddish brown hair, very pale skin, a smattering of tattoos down both arms; maybe 100lbs. Her face certainly wasn't model hot, but she had a nice smile and her tiny body looked like a fun time.

We matched and right away, she sent me a message about one of my prompts. In the online dating world, a woman sending the first message in any meaningful is unicorn rare (Tanya was one of the few) and Annie actually put some thought into hers, so we quickly engaged in a fun little back and forth.

Catching an immediate vibe, I wasted no time to secure a date. She lived a little far away and had an early work schedule, so I decided to meet up in her neck of the woods. I looked up places that I thought would fit the bill, mostly places I had either scoped out for prior dates, but one or two that I had been to before.

That outgoing, aggressive nature she had from the first message didn't even allow me to properly plan. She came up with a good spot - a barcade - that worked perfectly. In the meantime, we messaged pretty frequently and she was very open sexually, which was a total turn on.

Now, she didn't talk sex all the time or get into anything really racy, but she did mention that she's sewn her oats and looking for something deeper. I played with that a little bit to tease her lightly and she gave it right back, even making a comment about penis size. I was happy to play along as I have learned that I have a "Goldielocks cock" - not too big, not at all small, juuuuuuust right. She liked that a lot.

I ended up a there a little earlier than I usually do and she underestimated her drive time so she was late. After about a half hour in the parking lot, she announced her arrival and I met her at the door.

Her profile pictures were very accurate, though I did find her cuter in person. She's simply not very photogenic. She had a bit of an alternative look with 90's style low rise jeans, an oversized zip up sweatshirt, and a messenger style bag as a purse. It's a look I like and reminds me of my youth. She was very, very tiny and confirmed when we finally sat down for a drink and to eat that she was indeed 100lbs because she had "gained a little weight" in the last few months, not that anyone could tell she had an extra ounce on her.

Before we ate, we went around and played a bunch of games, taking turns back and forth picking them out. I marveled at her cute little booty; juicy little handfuls painted into her jeans as she led us to her games of choice. We were both a little flirty, but I couldn't quite read how much she was into me, though I could tell things were going well. After one of the games, however, I got a little close and she practically jumped up and kissed me, biting hard on my bottom lip. I put my hand on her hip, feeling her exposed skin as she stretched up to my mouth.

We played a few more games, shared a few more kisses and my wandering hand felt her exposed side - just a tiny bit of soft over the firm lean body. Crazy sexy. A couple hours of games and we sat down for a drink and to get some food in us.

Conversation was easy enough. We ate some wings, had a couple drinks, and when I acknowledged how late it was getting, knowing she had to be up really early, she was quite firm on not wanting to end the date. We talked for almost 3 hours and I had grown to be quite attracted to her.

Eventually, I called it a night to preserve her sleep time and account for my commute a bit. I walked her to her car and we started making out again. My hands found their way deep up her shirt, her flexing ribs and tiny bit of love handle fluff under her pale silky-smooth skin was driving me wild.

"I feel like I need to make a decision," she said, almost under her breath.

"What decision might that be?"

"If I should ask you to come home with me?"

I smiled. We had a bit of a back and forth, me playing it cool and hoping deep down for a true invite with her hemming and hawing about it being a good idea or not. She was new to online dating and had other dates set up, but felt like she shouldn't bother because we had such a good date.

I'm not going to lie, that sort of brute honesty and quick move to make a decision, frightened me a bit. It's not that I want to work too hard at it, but also am not trying to hurt anyone or waste anyone's time. I was very attracted to her, but not sure it's a long term fit or not and frankly, I tend to date prettier women.

After a little more back and forth, I pulled the trigger.

"It's time to make the call. I don't want you to cancel your dates and I have others lined up as well, but I do want you... bad. Let's go to your place, see what happens, and then go on these dates to make sure. How does that sound?"

"You want me to go on dates?"

"Not particularly, but I also don't want to get wrapped up in one good date, maybe sex if we go to your place, and rush into anything."

"I don't want to rush it, but you've set the bar pretty high."

"I do that. We're still just getting to know each other, but there's definite chemistry I'm not going to deny."

"So, you're coming home with me?"

"Absolutely."

Following her back to her place, I was pretty excited. I've never had a full-on hookup on the first date, ever. Bar and party hookups, getting super frisky on the first date. As much as I date and as open as I am to sex, I was kind of shocked when I came to that realization.

A bit of a panic followed as I pulled into her apartment complex, realizing that I didn't have any condoms. Oh well, we could always just fuck around. Still, plenty of fun could be had.

Going inside, it was pretty obvious she was planning this either. Her place was a mess. She had just moved in and shit was everywhere. After apologizing 100x and taking her dogs out to pee, we settled in with some little bottles of wine from her fridge and began making out.

She sat on my lap and we kissed for a few minutes before I suggested getting more comfortable in her room. She led me through the boxes and warned me, "sorry, I only have a twin bed." I didn't get into why she only had a twin bed, but she had a lot of stuff and was pretty recently out of a long-term thing, so I assumed it was a space issue and the bed she shared before was grown up size.

Rather than trying to strip down in such a small bed, I went ahead and dropped any coyness, along with my pants, peeled off my shirt and jumped into her bed in my boxers. We began to kiss and I started pulling her clothes off.

Her body is fucking incredible. Lean, with a tiny bit of softness. Adorable perky little tits that look like they belong on a woman 20 years younger. Those various small tattoos up her arms spread around to her back and sides, which isn't my style, but I didn't care at all. She was on fire. Nice handfuls that stand straight out, tiny nips, and quarter-sized areolas that shrink to nickels when you suck on them. As I got her pants off, the star of the show, as I suspected, was her outstanding ass.

A little round bubble, the perfect balance of soft and firm, with cute dimples just above it; I couldn't keep my hands off of it. She began stroking my hard cock through my spandex underwear as I pushed her cotton panties off her ass.

"You're pretty big, let me grab some lube."

"I don't have condoms."

"I have some."

"Good girl. And you don't need lube, I'll take care of that."

After retrieving a condom buried in a box in her hallway, she jumped back into bed. I began rubbing her moist pussy as she pulled me out of my underwear, tugging firmly. Her little pussy was getting juicy as she writhed and we kissed, my finger still just circling around the tight opening. I rolled on top of her and began kissing her neck, ear, then worked my way down to her perfect tits, sucking back and forth between them and marveling at her sexy little nipples. Kissing down her stomach she let out an audible, "Oh!" as if she was surprised that I was about to lick her.

I dove right in past her soft stubble, sucking her prominent hood and tonguing her minimal lips, dipping my tongue into her little honey pot every few laps. She twisted and ran her fingers through my hair, panting lightly with soft moans. I slipped a finger into her warmth, searching for her G-spot which was much deeper than usual. Unable to reach it effectively, I gave up and focused aggressively on sucking her entire pussy into my mouth, flicking my tongue up and down her clit as she grinded side to side.