The 50-First Dates Ch. 41-50

Date #41: Hannah the Prude

That's unfair. Hannah was NOT a prude. She was just a really good girl that refused to rush into anything physical because of some really bad past experiences. We dated for a couple of months and never got past 2^nd base. It was a little frustrating because I think sex is a huge part of a relationship, but she was so beautiful and so much fun I couldn't help make her my girlfriend anyway.

This is where things get interesting. I won't go into too much detail about who Hannah is or what she looks like because like Icarus should have known, I don't want to fly too close to the sun. Not that I think there's any chance in hell of it circling back around to her, but she knows my ex professionally. Not that I think it really matters, but rather than potentially opening a can of worms for her, I'll just let you use your imagination on this one. Hannah is HOT. Stupid hot. And awesome.

She's awesome and we had adventures in our short time together. I'm sure the sex would have been good, but I couldn't keep waiting around. In our intimate moments I felt her holding back and I feared that would continue into the most intimate moments. I require my woman to be completely free in the bedroom. No inhibitions.

Compounding the sex issue was that I felt like she was really falling for me and it was scary. It wasn't scary because I wasn't feeling it too, it was scary because if the sex was bad, I knew I'd be immediately switched the other way. I was really worried about hurting her because she is just a really sweet person and she had been through a lot. During that time, I was all fucked up, but the last thing I want to do is leave a trail of destruction, especially with someone so great. Maybe it's unfair to her, and myself, but I'd rather just cut the losses early than have it all blow up later when the investment is deep.

Ok, legal disclaimers out of the way, onto the dates.

Our first date was our shortest - 5 hours. We met at a boutique spot that specialized in local wines and oysters. She actually beat me to the spot which is something I almost never let happen, but when a woman shows up 20 minutes early, there's not a whole lot I can do.

As I approached, she guided me to an open parking spot she had scoped out, giving me a taste of how I handle my dates. I met her out front and as always, she looked hot. Conservative-ish short dress with a hint of cleavage and her hair pulled up in a pony tail, something I casually mentioned liking when we were first talking.

We got a table and the conversation was effortless. We talked about our lives, our pasts, values, goals, and all the things you really need to touch base on when you're getting into a relationship with someone. As you'd imagine, we talked about our exes and found a lot of common ground there.

It was great. We had a lot of fun, ending up chatting until they basically had to kick us out. From there we headed over to a pool hall nearby to shoot some pool and play darts. We never ended up doing either, just sat outside and talked over a few beers until 1am.. on a Wednesday.

Very quickly it was obvious that this wasn't going to be just some flash in the pan. We got really deep and honest right off the bat. There was little of us 'putting on our best faces.' It was deep and honest from the jump.

I walked her to her car, wrapped my arms around her, and gave her a little kiss. That kiss quickly turned into something deeper and my hands, gentlemanly, stayed respectful with my finger raking and light pawing being reserved to her back, hips, and outer thighs.

"You sucked my lip!" she giggled.

"And you liked it."

"That was fast!"

"You didn't like it?"

"I didn't say that, but it was maybe a lot for a first kiss."

"Our first kiss was about 10 minutes ago. Now, we're making out."

"Ohhhhhh, ok. Well, I guess it's time to go then."

"One more," I smiled.

She grinned, "just one."

Another quick peck and I opened the door, closing it behind her and giving her a little wave as I walked away. I always check in with my dates to make sure they got home ok and when I did, she fired right back, asking about another date.

Date number two was just a couple of days later. I actually cancelled another date because I just had a feeling with Hannah. The second date was more of the same. Dinner, hit a bar until it closed, make out, then text ourselves to sleep. It was really nice.

The following week we went on date 3 and it was a totally adventure. We ate a spot I like and my normal plan of a romantic walk by the water took a turn pretty quickly. There was a chill in the air and I gave her my jacket, something later she would say really impressed her because she could tell I was cold the whole night. It's really amazing to me how basic chivalry is lost on most men. Simple things. Opening doors, walking on the street side of the sidewalk, giving a cold girl your jacket, etc gives you major bonus points with most women and I get compliments regularly.

One of the things that came up in our conversation was a weird goth bar nearby that neither of us had been to so instead of a quiet walk, we made our way over a couple of blocks, paid the cover, and walked into their weekly drag show.

Quite an adventure for sure. They had a sex doll propped up on the bar that she was totally intrigued with. We took videos of us pulling on its tongue and simulating sex with it. We took a bunch of Jello shots, sipped drinks, and evaluated the femininity of the performers. Noting a vending machine with various adult themed bags in it (think Spencer's Gifts in vending machine format), I paid the $15 for the "Don't Buy This On A First Date" pack.

Opening it up, we laughed going through contents that included a chocolate flavored condom, a set of naughty dice, a feather, a string of glow in the dark anal beads, and a folded centerfold straight from a 1980's Hustler. Of course, I wasn't going to let the opportunity go to waste, so I immediately started rolling those dice.

Kiss, lick, suck, bite, touch, tickle. Neck, ear, hand, lips, thigh, navel.

We must have rolled those dice and played with them for an hour, running through every combination imaginable, though she quickly deemed 'navel' to be off limits - too much for a third date. You'd think thigh would have been on there, but she was wearing jeans so I'm guessing it was less intimate for her when I licked her jeans. On one of her turns though, I did make her lick the woman's face I have tattooed on my thigh. "I guess making out with a girl on your third date with a guy isn't too weird" she joked.

Right after that third date it was obvious to me that she was going to be my girlfriend. I sent a message to Tanya letting her know and she, as expected, wished me luck.

Our next date was a 'movie night' at my place. This is my go-to when sex hasn't been established and I was looking to get establishy. She accepted with great enthusiasm and told me she was going to wear her most comfy PJ's. Game, set, match.

Nope.

She came over and we cuddled up on my double-recliner, drinking wine and getting cozy. While watching the movie, I started making moves. Rubbing her inner thigh through her fuzzy pajama bottoms and nibbling on her neck and ear. She was giving me green lights, but when I started rubbing deeper between her legs while pressing my hard cock against her thigh, she stopped me without a word. Just a light hand onto my hand telling me everything I needed to know. I reversed course and we continued watching the movie, eventually spooning and my dick riding between her cheeks.

More green lights as she pressed against my stiffness, so my hands found their way up her shirt. Teasing over her stomach as she turned back to kiss me, I found the underside of her bra. She turned into me further, allowing my hand to grope the outside of her thin bra. I fondled her tits, playing with her nipples through the silky fabric and played down into the top of her pants.

Flirting with the top of her panties, I traced my fingers down to feel her neatly trimmed pubis. That soft hand again.

"Are you not into this?"

"No, I'm sorry, I totally am. I just don't want to move so fast."

"No problem!"

A little more kissing and some less intrusive hands, we went back into our cuddle session and finished the movie. I pushed the footrest back in, stood in front of her, and reached out my hands.

"Are you kicking me out?" she chortled.

"Not at all, let's go get more comfortable."

"How comfortable?"

"As comfortable as you're comfortable with."

"I think we're good right here."

"Well, I would like to get more comfortable."

"I'm sure you do" she giggled. "It's not that I don't want to. God, I want to. I just know that the emotional investment of us having sex tonight is going to be very deep for me."

"And you're worried about my intentions?"

"No, no, not at all. I'd just like to take things more slowly."

"I'm sorry, don't want to make you uncomfortable. I'm just a very sexual person and I'm into you, so it just feels like a natural progression."

"I'm just not there yet."

"Ouch."

"Not like that! I like you too! I'm sure it would be great and everything, but I'm just not ready."

"Ok, no problem."

She offered to watch another movie, so we cracked another bottle of wine and ended up watching two more, just cuddling throughout. I didn't push my luck and frankly, in the moment, it was kind of nice being intimate like that without any chance of actually fucking.

That 'kind of nice' thing wore off the more we dated. Several more dates including karaoke until 2:30am, more dinners and bar hopping, and a beach date that turned into major trauma dumps for both of us and watching the sunrise together before having to scramble back so we could both be at work at a reasonable time. It was still kind of nice, but ultimately, after two solid months of dating I wanted more.

There were actually a couple of points along the way that I thought she was going to pull the plug on me. I kept testing the boundaries, never pushing too far, but it did stoke conversations about our sexual histories. She had only been with 3 men her entire life and I, well, you can guess my number is a little different. I was actually very surprised by how she handled it.

I fully expected her to run away screaming, but she didn't. She just insisted that when it was time for us to get it on, I'd have to be fully tested even though I shared my recent results with her. She was very level-headed and mature, which is very attractive.

Ultimately though, a little more than two months deep, I really wasn't feeling like waiting any longer. Nobody likes an ultimatum, so I didn't give her one. On the eve of our next scheduled date, I called her and talked to her for about an hour, trying to get a handle on where things were going.

She felt like we didn't know each other well enough and given her romantic past, I get it. By the end of it, I had my mind made up and I told her we weren't on the same page as far as our time horizons. I was kind of expecting her to have an emotional response, but I should have known better. Nothing shook her. She took it in stride, told me that if something changed, she'd like to continue seeing me, and we ended the call cordially.

I've since wondered what could have been with her, but I'm just terrified that we would get to having sex and I wouldn't be into it with her. The last thing I wanted to do was hurt her, so I did the wise thing and called Tanya again.

Date #42: Madison the Coed

I sat for a while, enjoying Tanya's sex and companionship (and wise ass comments about how I fucked up a good thing with Hannah because too much of my brain is between my legs), not doing a damn thing with the dating apps. It was probably about a month later that I turned it back on and low and behold, was sitting on an old 'like.'

Madison was cute enough at 5'2", had a sexy curvy body, and was 22 years old.

I've had these college age matches in the past and they go one of three ways. 1 - seeking a sugar daddy or someone to subscribe to their OnlyFans. 2 - a go nowhere back and forth, if anything at all, then a pretty quick ghosting. 3 - I'm unable to handle talking to them for more than a few exchanges before growing annoyed at their immaturity and unmatching them.

Ok, so Madison was a #4.

She was smart and mature, coming off as someone much older right away. I actually thought she was a catfish at first, but figured 'what the hell?' Pretty quickly we moved to text to set up a date. Right away it was obvious she was real and the generation gap was strong.

Soon, she began sending me little personalized videos of... nothing. Her doing her nails at work, her singing along to a song and replacing names with mine. Random videos of her walking and talking. Just periodic touch bases several times per day until our schedules aligned so we could go on a date. Tik Tok generation.

It wasn't all bad though. We actually had a decent text convo here and there. She was quick to identify the age gap and I was quick set expectations. "Oh, I'm not looking for anything serious with you. You just seem like a good time, Pookie."

And there we had it. Just a good time. Perfect.

I arranged a date by the beach, basically that first date with Brynn the terrible kisser. Right away when I met up with her, I regretted the restaurant choice. She was a burger and fries girl and this was a linen napkin and "would you like to see a wine list" sort of place. It didn't matter though because she looked hot and I was interested in checking that place out again anyway.

She called me when she pulled in and we met in the parking lot before going in. She was wearing tight jeans that highlighted her excellent curves and a bright pink tube top that left little to the imagination. Her shoulder length brown hair accentuated her youthful face like heavy silk curtains.

She was cute, not overly pretty, but her short thick body would make the Pope rubberneck and crash his bulletproof glassed armored car. Her outfit wasn't totally jiving with the vibe of the restaurant and the eyeballs we got were noticeable. Water off a duck's back though. The sneering looks were honestly great. Women my age looked disgusted and their husbands looked envious.

Surprising we had a decent conversation over dinner and it didn't take much to convince her to take a walk to the beach. Stopping at my truck to break out the standard "beach date backpack", we ventured in the moonlight onto the desolate and windy beach. After setting up, we got straight to business.

I cracked a bottle of wine, poured two glasses, we toasted our first meeting and she immediately started kissing me before we had our second sip. She was a great kisser and my hands roamed her curves, my nether regions stirring with a quickness. Just as things began to heat up, sneaky fingertips fluttering over the taut skin of her bare midriff and teasing the underside of her tits, the wind whipped up and huge drops of rain began hitting us with rapid intensity.

Scrambling to wrap up all of our shit, we darted back up to the road to search for cover. A park was right along the way with several secluded, pitch-black pavilions. We got there just in time for the rain to absolutely pour, set up shop there and continued to make out standing next to the tables. She paused as my hands reached down the back of her jeans.

"Oh my god, you're obviously experienced."

"I have a year or two on you."

"That's right... old man. I think you do this often."

"Make out and get handsy under a pavilion in the pouring rain?"

"Something like that."

"I think you do this too. You're not wearing any underwear."

"I never wear underwear."

"And no bra."

"Not with this top and these tits."

"Let me see."

I licked up her neck, nibbled her ear and slid my hands up the back of her top, around the front, and cupped her DDD's.

"Nice."

"You're bad, Pookie."

"I've heard that before."

"From how many thousands of girls?"

"Thousands? I don't know? Maybe 10... 20 thousand?"

"I bet."

Pulling her into me, I tongued around the inside of her mouth and rubbed down her side into her pants, sliding around to her ass and grabbing a big handful of her firm, voluminous flesh. Pawing with both hands, I pulled her into my titanium rod. Our teeth gnashed together as I ripped my grip on her amazing rear end.

I shifted slightly to her side, slipping around the top of her jeans and reaching for her pussy stopped only by her jeans being just a little too tight.

"I really didn't expect all this," she purred as I unbuttoned her pants.

"Am I meeting expectations?"

"I didn't shave."

"I don't mind."

My fingers parsed through her delicate stubble, finding her ample mound leaking profusely. She leaned her head back and I licked and nibbled her neck as my fingers stroked up and down her slick little slit. Taking my hand from the back of her pants I grabbed her arm and placed her hand onto my member. She tugged lightly through my shorts and I helped her unbutton, unzip, and pull me out of the top of my boxers.

"Wow, Jack. It's nice."

"I think it likes you."

"I think so too."

Wrapping her dainty fingers around my thickness and yanking roughly, she moaned when I parted her lips and traced her opening.

"Easy, not so rough. You're not trying to take it home with you, are you?"

"I might" she breathed.

"I might let you."

I plunged a finger in and she squirmed, her violent tugging now calmed to a firm stroke.

"Do you want to get out of here?"

"I'm not fucking you tonight if that's what you're asking" she squeaked as I fondled her G-spot.

"That's fine."

"I want you though."

"You can have me."

"Oh fuck, keep doing that, I'm going to cum."

I circled her G-Spot with increasing intensity until she began to quiver and shake.

"Yeah daddy, yeah! I'm cumming!"

Her hand was still squeezing my dick, but wasn't moving as she nearly collapsed into her orgasm.

"Oh god that was good. You're really good at stuff."

"Tens of thousands."

"No doubt."

The rain was subsiding and it didn't seem like she was too interested in finishing me off so I just let it go, wrapping things up, pulling ourselves together, and walking her back to her car. We shared a kiss and I went home, wondering if it was one and done or if she was interested in more. I kind of figured she would be so I wasn't surprised when she texted me the next morning.

We shared memes and gifs a couple of times a day for weeks before we could get together again. I clarified a few times to make sure she didn't have any ideas of any sort of relationship and she played along perfectly. Finally, our schedules aligned and she agreed to come over for "movie night" on a Sunday evening. Just as always, I requested comfy clothes.

I was hoping for something a little sexy, but she dressed as I requested. An old Def Leppard t-shirt and black leggings. Not exactly a sexy outfit, but her ass was banging and her big braless tits swung as she moved, her hard nipples leading the way..

I offered her a drink, poured us both some wine, and she proceeded to be awkward. Making silly comments and doing strange little dances around as the maturity gap finally showed its full teeth.

"Do you want to start a movie?"

"I guess."

"That doesn't sound too enthusiastic."

"I really didn't come for a movie, but I think you know that."

"Just trying to be a gentleman," I laughed.

"I didn't come here for that either. Is your room over here?"

She moved towards the hallway.

"Nope, over here."

I pointed across the room at my closed door.

"C'mon!" she skipped past me, lightly jostling my junk through my athletic shorts and dancing into my room.