The 50-First Dates Ch. 11-20

Date #11: June the Ghosted

Another Latina. I was on a roll with the Hispanic ladies. After Lisa, it seemed like every woman in my feed was Latina. Not a bad "problem" to have.

Like Angelica, she looked better in person than on the app. Tall, mid-30's, about 5'8", very thick and curvy. Her ass and thighs just didn't stop in her tight jeans. Nice handfuls up top, pale skin, and long straight brown hair down her back, she was sexy.

Her thick Cuban accent and cute mannerisms had me going right away. We ate dinner at a fun little Mexican spot and she insisted I sit next to her; our flirting was strong. We ate, we laughed, we had several drinks, and then we went to an escape room. She was smart and I'm no dummy, but those things simply aren't meant for two people. We failed miserably, but the pimple-faced kid in the front said he was impressed with how well we did.

I walked her back to her car and we made out in the dark space between street lights where she was parked. She was a good kisser, lots of lip sucking and swirling tongue, and my hands were all over her large firm rump. God, I wanted to fuck her, but she paused once my hands found the soft skin of her back and played with the silky top of her panties just inside the top of her tight jeans.

We agreed on a second date, but over the next week her communications turned. She got very serious, very quickly. She talked to me like we were already in a relationship and effectively love-bombed me to the point in which I got uncomfortable. I stopped responding and a few days later she called me out for ghosting. I confessed that I wasn't ready for the energy she was bringing and she handled it perfectly. She wished me luck and I was free once again, not that I wasn't free the entire time.

Date #12: Ava the Adorable

Adorable. Ava was adorable. She was close to my age, tiny, and super cute. She had shoulder length blond hair, big beautiful blue eyes, and a sexy little smile. Another one with kids, but they were older so not to cramp on any of our plans.

Our date seemed like a glowing success. We ate sushi, laughed and teased, and I wondered what her little squeaky voice would sound like as I ravaged her petite body. After dinner we went to a place that had a bunch of arcade games and axe throwing.

She kicked my ass on the axes, though there at the end I found my flow and was doing pretty well. The best part about it was me getting to really take in her body. She wore a tight sweater that was just short enough to see a bit of midriff as she moved, full on belly as she hoisted those axes over her head. Yum. Her plump little ass and supple thighs looked amazing in her painted on dark jeans and "fuck me" boots.

We laughed so much and had such a great time that I was sure there would be a second date when I walked her to her car. We made out light high school in the mostly empty parking lot. In fact, she actually said, "this date makes me feel like we're still in high school", that same feeling I've had in many of my dating experiences.

Hot and heavy, my growing swell pressed against her as my hands were all over her soft, squishy ass. I left her wanting more and we texted a bit after we both got home, then the next day, she was gone. Never heard from her again.

Date #13: Liz the Big

I had been very skeptical of any profile without full body pictures, for very good reason. Liz was so damn beautiful though; I couldn't help myself. I had to find out.

A gorgeous Puerto Rican redhead in her early 30's. Pale skin, bright blue eyes, and very busty. Model good looks. I figured she was fat, but I couldn't resist after the brief phone call she insisted on before meeting. The conversation was fun, her subtle accent was sexy, and we shared similar interests and values. She was just fucking stunning on her profile and there definitely was a vibe.

As suspected, my heart sank when I met her for our first date. She was fat. Nothing crazy, but too big for me. She carried it really well over her 5'2" frame, but she was just too much. I decided to make the best of it and we had some beers at a local brewery. The more we talked, and drank, the more attracted to her I became. She might be the prettiest woman I've ever talked to, but the further down you looked the worse it got.

Fuck it.

It was close to Halloween so we jumped in my truck and headed to a haunted house nearby. She was big into horror movies, just as I am, and we were having fun so I gave it a chance. The setup was fun and we got in some good scares, but the beers were wearing off and the reality set in. I wasn't fully attracted to her.

Back at the brewery, I parked next to her car and went for a hug. She didn't want a hug. She just started kissing me. She was... the perfect kisser. Nibbling lips, wonderful tongue technique, and a great mix of hard and soft. Holy shit! I WAS attracted to her.

I grabbed big handfuls of her enormous plush ass. My cock sprang to attention and pressed against her stomach. She giggled, "I'll look forward to feeling that in the future."

Getting back in my truck, I was looking forward to her feeling it in the future.

I still had some reluctance, but she definitely turned me on so I continued talking to her and set up a second date. Sushi and a walk in the park.

She showed up in a skin tight grey dress that highlighted her mountainous curves. The night before, I had a boring, go nowhere date with a girl who was maybe half her size. Very petite. That ended the way it began, with a hug, and the second I saw Liz and gave her a hug I wanted out. I couldn't do it. Feeling the contrast from my date before was too much. She was too much woman.

Dinner was fun again and she was still so damn pretty, but I couldn't stop thinking about the body of my date not even 24 hours earlier. She insisted on paying and I went through the motions. We stopped and talked at the fountain in the middle of the park and she was again, very aggressive.

Her kissing was so high level, she drew me back in. We kissed on a bench for a few minutes until she hiked up her dress enough to mount me. My hands roamed her body, finding the porcelain skin of her chubby thighs, up her dress and over her ass. I felt the dimples and divots, unable to really get a grip because it was just too big. The kissing couldn't make up for my lack of attraction to her body.

I stopped things a few minutes later, said I was tired and wanted to go home. I gave her a hug at her car and she texted me the next morning asking if she had done something wrong. She felt my lack of attraction. I simply told her that I wasn't feeling a strong connection and didn't want to lead her on. She never responded.

Date #14: Laura the Busy

Perfectly imperfect. A great match for another time, I guess.

Laura and I hit it off immediately. Similarly accomplished in her career and our politics were identical. We were both hardcore 3^rd party people and she actually had met one of my heroes in the movement at a conference she was attending.

I was impressed right off the bat. She was probably the smartest woman I had talked to up to this point, but she was also funny. We ebbed and flowed in and out of deep and silly - top tier banter.

I figured I needed to work some real magic to impress a woman like this on our date. Pulled out all the stops. I set up a fancy dinner at a nice Italian restaurant in honor of her deep Italian roots, with plans to take in a nearby attraction.

Meeting her in the parking lot, I was not disappointed. She was very pretty and the perfect type of curvy. A great mix of soft and firm. Average height, pale skin, black hair, and a gorgeous smile. She had just the right amount of hips and ass and pretty big tits hiding under her fuzzy red sweater.

Just as I planned, the date went perfectly. Dinner was great, the attractions were fun, and we made out like kids on the giant Ferris wheel. 7 hours and almost $500 later, I figured I had a keeper.

Nothing slowed down at that point and throughout the next week we scheduled a second date. This one couldn't be so prolonged due to her work constraints, a sign of things to come.

We shared IPA's and ate garbage food, wildly swinging clubs at Top Golf. I had so much fun with her that evening and I was getting major girlfriend vibes. Just like our first date, we ended the night next to her SUV, laughing and flirting, sprinkling in some kissing. The place was closed and one by one the employees pulled out, leaving us completely alone.

Under the cover of the desolate area, our kissing grew more and more passionate. My hands found their way into the loose waist of her jeans, immediately pawing over her plump booty in her satin high cut panties. In and out over her smooth skin, I ran my hand up her shirt and teased that I was going to undo her bra. She giggled and stopped me, but was unrelenting with her mouth on mine.

Back into her pants, I traced around to the front and unbuttoned her pants. "Not here" she purred.

"Don't worry, I won't touch you there."

She licked my neck as I ran both hands down the front of her jeans, feeling down her thick thighs, and teasing back up the inside and lightly grazing her moistening panties.

"That's enough for tonight. Next time." She smiled as she pushed me back.

"So there will be a next time?"

"I hope so."

There was no next time. We tried and tried for weeks to set something up, but her schedule was brutal. We just couldn't make it work. At that point I decided I couldn't be with someone who had such a demanding career. It's a mistake I still make, but I still think of that experience and what might have been when I discuss the work habits of the women I date.

Date #15: Melanie the Educator

This smokin' number taught me a valuable lesson. You can't try too hard until things are established. Don't waste your time and don't push too hard and get your shit in order for when someone really interesting comes along.

Melanie is hot. Tall, blond, kinky curly hair, "wow" smile, sexy librarian glasses, and a lean little body with big double-D's. 30 years old, no kids, no plans on kids, and really fun. She was very slow to meet at first, given she was just out of a toxic relationship, so we spent weeks texting. I knew at this point I shouldn't invest that much, but the little head was running the show.

Eventually we got on the date and I was not disappointed. At first, I couldn't tell if she was really in to me, but I realized and important another lesson that night. If a woman won't shut up, it could be because she's nervous and trying to impress you.

The date was one of my standard runs. Dinner at a place I like, drinks at a cool lounge right down the road, then sit by the river and cuddle on the big bench swings. I've ran this date at least a dozen times and it's always a crowd pleaser.

While at the lounge, the wine was kicking in and she just wouldn't shut the fuck up. Talk talk talk talk talk. I was kind of annoyed, not reading the signs right, but I did start rubbing her leg to see if there was interest. She loved it. Next thing you know, the place is closing and we're cuddled up on the couch, her mouth never even taking a breath between subjects.

On our way to the final stop, she confessed that she looked me up. Looking me up is an understatement. Her cop friend ran a full background check on me. It was unnerving, but given her past and the horrors of the online dating market, I got it. She was very sweet about it and clearly embarrassed.

We found a bench, chatted for a while, then I walked her back to her car. We kissed and kissed and my hands wondered her perfect body. They nearly wrapped around her tiny waist as I dragged my fingertips up and down, over her lean thighs and gripped her hips to pull her in tight. I wanted to consume every inch of her. She laughed and hit the pause button as I groped her taut little butt.

I really struggled to control myself. As she got back into her car, I pushed for another kiss and she obliged, but seemed a little turned off. It went from hot and heavy to "I think I fucked up" like a light switch. She got in and I started to close her door, but she pushed it back open and tapped her finger on her pouty mouth. I grinned, leaned in and gave her a nice little kiss and made my way back to my truck.

The next day we set up another date and I made a bigger plan. Farmer's market, early dinner, little pedal boats on a nearby lake, and then drinks at a hidden gem of a bar overlooking the water.

When I met up with her, I immediately picked up where I left off, going for a kiss straight away. She turned her head into the hug and it was awkward, "Oh, you wanted to kiss me?" I nodded and she gave me a nice little kiss just like the one we ended with a few nights before.

The conversation was good, but I did notice she wasn't talking as much and was asking a lot more questions. She did divulge some of her interesting sexual desires - specifically wanting "to try" a facial and her propensity to be turned on hearing about her man's past bedroom experiences, and I had plenty to share.

We walked the farmer's market holding hands and I felt like we were going to be a good couple. I found a girl who I could really see working with on a more serious level. She complained about a sore neck at lunch and I rubbed her shoulders. She stopped me saying my strong hands were turning her on too much. I laughed and apologized, leaned in and kissed her neck and whispered in her ear that she could have my strong hands any time. She confessed that my deep voice in her ear like that was getting her wet.

This was going, very, very well.

After we ate, we shared a bottle of wine and continued to chat. More about me than her and I just figured we were finding a balance. Out of nowhere, she mentioned that the kiss at the beginning of the date and the hand holding made her uncomfortable - "I like you, but that feels too fast." It was downhill from there.

It was unseasonably hot and she was not into the peddle boat idea at all. No problem, we skipped that and went to the bar. The chatterbox from the first date had slowed through this second date and I felt like I was trying way too hard. It ended well enough, more kissing and touching, confirming a 3^rd date before parting ways.

That next week I noticed our texting slowing way down. I found myself forcing the situation by asking a lot more questions and not tending to the flow as it was. For our last date, I revisited the local attraction that was so successful with Laura.

Off the bat it was different. She was distant over dinner and seemed like she was someplace else. I panicked and began forcing the fun instead of my usual go with the flow pace. She had mentioned being afraid of heights, but I pushed for the Ferris wheel ride anyway. Uncomfortable the entire time, she sat cutoff from me physically as if she was trying to make herself smaller, obviously nervous. I tried to comfort her and cuddle with her, rubbing her arms and holding her tight. I fucked up.

I really fucked up as we walked back to her car and asked a question I had already asked in our texting and was met with the dreaded, "we already talked about that." Fuck. In my haste to impress her, I tried way too hard and didn't just let things happen as they should. We had a little kiss at the end and after a few text messages that week, she said she wasn't feeling like it was working and wished me luck.

I totally screwed the pooch with Melanie. I got way too excited about her too quickly, invested too much, and in my haste to making something out of that great first date, totally forced things. I guess I was insecure for some reason - maybe because she was so hot, maybe because I got out over my skis trying to make us a thing way too fast. Lesson learned. Back to just relaxing, going with the flow, and not getting to excited so quickly. Most of the time.

I've seen her pop up on the apps over the subsequent months and one time I sent her a quick message. She matched and we had a little conversation. Just as I was about to ask her out again, she deleted me. I guess it just wasn't meant to be.

Date #16: Lucy the Friend

The initial stages of this thing weren't anything to write home about. Lucy was a very attractive, petite single mom in her early 40's struggling with a lifetime of tragic relationships and very lonely as a brand-new empty-nester. She was a little weird, but her little 5'2" curvy body was very sexy and her ice blue eyes were mesmerizing.

Our second date ended up with a solid make out session in my truck and getting a little frisky in and out of her jeans. I wasn't sure where it was headed, but I liked playing with her. We got to talking a bit after and made the decision it really wasn't going anywhere despite the physical attraction. I wrote her off at that point, wishing her well and moving on.

A couple of months later, out of the blue, she texted me. She was drunk, but had been thinking about me since that second date. She lamented the terrible dates she had been on since and praised me for showing her a good time and making her feel safe and comfortable. As we talked, she admitted she was done with dating, but needed some sort of physical outlet.

'I could come... fill that void.'

'I bet you could.'

'I bet you'd like that.'

'I would, but I'm not a slut.'

'Sluts do it with everybody. A friend, with benefits, only does it with one person. Like a relationship, without the relationship.'

'Come and get it before I change my mind.'

She lived on the other side of town and I raced over as fast as I could, hoping she wouldn't change her mind. She greeted me at the door braless, in an old t-shirt and sweatpants that hung loose off her petite frame. Her crimson highlights were stuffed into a bun on the back of her head and her deceptively large tits swung back and forth. She offered me a glass of wine and told me to find something good on TV.

I plopped on the couch and scanned Netflix, then she handed me a glass of white and cuddled up next to me. Wrapping my arm around her, I tickled the outside of her arm and leaned forward to nibble her ear. She spun into me, sliding on top and kissing me deeply. My hands ran down past her open waistband and onto her soft pantyless ass. Moaning into my mouth, she rocked forward as my member throbbed against her stomach.

Pushing her back as I sat up, I peeled my shirt over my head and reached for hers, unveiling massive hanging tits. I took them into my hands, sucking her big nipples and turning her 50-cent piece areolas into tight quarters. She ground herself against my fat cock under my thin athletic shorts and ran her nails through my hair.

"I want you."

I bowled her over onto her back and pulled her sweats off, casting them onto the coffee table. I reached my pocket, put the condom in my mouth, and pushed my shorts down.

"I can't with a condom. I'm allergic to latex."

"I try not to have unprotected sex."

"I appreciate that, but it's been nothing but these two fingers for almost 5 years. And I got tested twice after that asshole."

"I can pull out."

"You don't have to, I'm fixed."

Diving in immediately, I bit her neck as my bulbous helmet pushed into her hairless squish. Sliding in and out as her nails raked my back, I felt the depths of her empty womanhood, lacking the typical cervix and uterus bottom.

"I want to feel your weight." She moaned as I held myself above her.

Wrapping my arms around her back and neck, I allowed the full force of my body to press her into the couch. My pace increased as she moaned my name, "Jack... oh Jack... yes Jack... fuck me like that Jack... fuck me." Harder, faster, I pushed her deep into the cushions and filled her with every drop of my seed.