The 50-First Dates Ch. 11-20

Laying there sweating, panting, I softened and fell out, leaving a dark spot of our goo on the upholstery. Sitting back up in the corner I had a chuckle as she leaked her way into the bathroom to clean herself up. She reemerged, made a joke about why was I still there, and we finished our glasses of wine and I left.

We chatted more that week, acknowledged that if anyone got any feelings the deal was off, and I had my first true friend with benefits in decades. We got together randomly for almost 6 months, as much as twice a week a few times.

We discussed our dating lives, watched TV, and I gave it to her the way she wanted it every time. Me on top, pressing my entire frame against her, pound relentlessly and filling her up at least twice each time we got together. Like all good things, it had to come to an end. One night with my arms still wrapped around her, squeezing hard on her flowing tits and pressed balls deep against her soft little ass, both of us drooling out of her well spent hole, she mentioned her ex was coming back around and he needed a place to stay. He was in, I was out. No problem.

Several months later, she started texting again. Things didn't end up working out with them as you might expect and she took it hard, lost a bunch of weight (that she didn't have to lose), and was lonely again. We chatted a bit and I asked if I should come over. She agreed for another night, but when that day came, she backed out. She said she was ashamed of her body being so skinny, she wouldn't be able to enjoy sex. We've talked a few times since and it's possible we'll get together again.

Date #17: Bella the Bro

One and done with Bella. We vibed right away and her perfect smile, sparkling dark eyes, and cute curvy body had potential written all over it. Our banter was stellar and the mutual attraction was strong, but the more we talked on our date, the more apparent it seemed that we were destined to be nothing more than friends, if that.

Everything was almost in reverse with her. We got sexual right away before the date. We got right into it and it was very exciting. She grabbed me as we walked to the restaurant with a sly, "let's get this out of the way," planting a big wet kiss and slipping in a generous amount of tongue. Throughout dinner we talked as if we were an established couple just getting to know each other.

After, we held hands and walked to a dive bar and drank, sharing stories of our dating exploits. The conversation was great, but between her talking about all the guys she has friendzoned and me talking about all the girls I've kissed on the first date, all that sexual energy faded on both sides. We held hands and walked the park, somewhere along the way breaking free from each other and never returning to the other's clutches. I walked her to her car; we laughed about how nothing was ever coming of the date and we literally high-fived and parted ways. Definitely want of the strangest dating experiences I've had.

Date #18: Jenny the Holy

Jenny is a sweetheart. A little southern belle, 5'2", sandy brown hair, perfectly thick and curvy. She's cute, with her freckled button nose and big toothy smile, looking a bit younger than her 32 years would suggest.

We hit it off pretty quickly and had a fun little video chat before meeting up. She had gone through a lot with her ex so on our date I made sure to be the perfect gentleman. We ate at a nice Italian restaurant near the beach, shared a bottle of wine, and after dinner I suggested we go sit and watch the waves roll in.

Making my normal stop at my truck for beach supplies, I produced a bag with a couple of blankets, a bottle of wine, and an extra pullover to cut the chilly ocean breeze for her. We made our way to the beach, laughing and playing with each other, just good clean fun.

After making up our spot, she pulled the fleece over her head and we popped the bottle of wine. We sat and chatted, finishing half the bottle in no time. She was such a nice girl, I wasn't sure how things were going to go, but laying there next to each other I inched closer and closer as we talked. I smiled at her, looked deep into her eyes, and kissed her gently.

Our passions grew as the light kisses turned into our bodies pressing tightly against each other, tongues fluttering deeply into and out of each other's mouths. The wind picked up as the night wore on and we found ourselves under the extra blanket I brought.

We flowed into and out of heavy making out and conversation. Each time we came back together, my touch moved further. Kissing, teasing my hands on her hips, thighs, sides and back. Talk a bit. More kissing, my fingertips finding their way under the pull over and teasing the skin along her side, lightly into the top of her jeans and up to taste her bra strap. More chatting. Deep kisses, fondling her D's and plump, thick ass in and out of her clothing.

"I'm afraid I'm about to do something I'll regret."

"We don't have to do anything you're not comfortable with."

"What exactly are you looking for?"

"I'm not looking for anything. I have no expectations. I'd love to find someone I vibe with and can spend some time with, but don't want anything too serious."

"You don't just want sex."

"Not just sex, but of course, I do want sex."

"Do you sleep with a lot of girls?"

"No, I'm not a hookup guy anymore."

"I'm looking for a relationship."

"I could be open to that, but I'm not going to rush that side of things."

"Just rush to sex."

"It doesn't have to be a rush. You're sweet, I like you."

She kissed me lightly and we cuddled, staring up at the stars, bundled together under the clear sky. It was getting late so we called it a night. The rest of the week we talked every day and set up another date. She was working a little late that night and wanted to skip dinner to have another night at the beach.

I picked her up at her house where we had a glass of wine and chatted on her couch. She was only 15 minutes away from the beach so we finished our glasses of wine and headed over. With my 'beach date bag' packed on my back we walked up the beach for miles, just flirting and talking. Realizing we were in the middle of nowhere, we decided to set up the blankets and relax under the bright moon.

We talked a bit more and she ran her ice-cold hand up my shirt, and started kissing me fervently. I struggled to dig my hands all the way to the bottom of her jeans, gripping as much of her smooth firm cheeks as I could. My hand moved around to the front, but was stuck on her hip. I retracted, feeling my way to her button and flicking it open. Her breath shuttered as I unzipped her fly and ran my fingers on top of her silky thong, finding a mess of excitement permeating the fabric.

I rubbed her wetness, my cock straining to break free of my restrictive shorts. She laid onto her back, spreading her legs open and my sopping fingers found their way under into her panties, massaging her neatly trimmed lips. I kissed her neck and pressed my hardness into her thigh. Reaching down to guide my hand at first, she bucked slightly, forcing me away.

"I'm sorry, is that too much?"

"No... I mean... yes. I don't know. It's been a really long time since I've been touched like that. And this is a still just our second date... I just... I don't know..."

"No worries, just relax. We don't have to do anything you're not comfortable with. I like you and I'd like to take you out again. Are you ready to go?"

"No, can we just cuddle again?"

"Of course!"

I wrapped my arms around her and pulled her close, pressing my rock-hard manhood against her.

"Wow, you're excited." She giggled.

"You're hot, what do want me to do?"

"God, I want you to do everything."

"That's not what I meant" I smiled.

"I know, but you feel so good."

We cuddled and chatted again, discussing our relationship goals which seemed to align more and more as we talked. I realized she was more interesting than just her sexy body and she realized a little fun was exactly what she needed. We found a balance and started kissing again under the blankets.

She sucked my lip and pulled my shirt up to my armpits under the blanket. I peeled it over my head and we resumed kissing. Playing with her ass and we ground into each other, her pants slowly slid down to her thighs. Reaching back deep into her crevasse, I found her little honey pot again from behind, dripping with slickness.

Her mouth pushed hard against mine and our teeth gnashed together, tongues straining to find every last bit of each other. Her hands ran from my back to the front of my shorts, awkwardly ripping at my button. I reached down, opened the button, dropped the zipper, and pulled my boxers down. Her cold hands gripped my shaft and tugged energetically against her bare stomach.

I ran my hand up her back, unclasped her bra, and pushed underneath it to grope her big, supple breasts. Teasing back down over her stomach, I plunged my hand into her sodden panties and parted her lips with my middle finger. She moved to her back, still pulling my dick with one hand and pushing her jeans down further. As my finger traced her opening, she lifted her shirt and bra up over her chest, exposing her big, beautiful rack.

Sucking and biting on her little eraser nips and token sized areolas, she began to pull me on top of her. Her legs were stuck together with her jeans by her knees and I sat up and pulled them the rest of the way off. I climbed on top and began rubbing myself over her panties, my steel rod glistening with her essence.

I felt her body grow tense as we kissed, my cock pressing hard against her wanting pussy.

"Are you ok?"

Her eyes remained closed and she nodded.

"Are you sure?"

"I really want you."

I raised myself up, and pulled her panties off, lowering myself back down with a quick suck of her nipple and ran my girth up and down her steamy slit. I paused slightly, broke free from our kiss and stared into her eyes. Her mouth was agape as our eyes were locked and I slowly slid inside of her burning hot canal.

She was so tight and so sexy, she had me coming in just a couple of minutes, pulling out and firing a hot rope between us.

"Sorry, that was a little quick."

"No, it was perfect. I'm going to feel it in the morning."

"It's been a while, huh?"

"Years."

Putting ourselves back together we laughed and talked a bit more, returning to our vehicles, discussing another date the following weekend.

The more we talked that week, the colder her feet got. The day after that date she mentioned she was going to church. We had previously discussed religion and it was obvious we weren't compatible in that way. She wanted a man who would go to church with her and I'm just not that guy. I tried to keep our second date, but she needed time to think.

We touched base here and there for a few weeks and she mentioned she reconnected with a guy she dated briefly before me. I wished her luck, called her my friend, and moved along.

About a month later she texted me out of the blue and referenced my friend comment as a joke. We chatted a bit and the guy she was seeing turned out to be a creep. She mentioned the nights at the beach, how fun they were, and if she was "a different person" she'd come over because she was sure, "I'd make her feel like a woman again."

May be the hottest thing a woman has ever said to me. And sure enough, just a few days later, she asked if I had plans for the weekend.

I invited her over and that night I grabbed a bottle of wine, lit some candles, and watched as she approached my front door on the Ring camera. She was wearing a cute little white dress that slightly highlighted her curvy little body. We sat on the couch, chatted and cuddled, drank the bottle, and watched TV.

I was toying my way up and down her smooth inner thigh as she finished her last glass of wine. She reached to the back of my head and pulled me on top of her. We kissed for a few seconds and I dismounted her, reached for her hand, and pulled her to the bedroom.

The clothes disappeared from my body before I crossed the threshold. Standing in the candlelit room, I pressed my nude body against her as we kissed. I stretched down and lifted her dress up and off her body, grabbing handfuls of her velvety flesh as my cock grew to attention. Pushing her onto the bed, I peeled the thong off, and buried my face in her well groomed hilt.

She moaned and writhed as I tongued deep inside of her, slurping and lapping her perfect little pussy with a fury. My hands ran up her stomach, pushing her bra up over her tits and she sat up to toss it to the floor. Her hand clamped to my head, directing my mouth everywhere she wanted it to be until she pulled me up for a kiss. My cock found it's home immediately as our lips touched, slipping in to her soggy pussy, wrapping my manhood in her dripping heat.

After grinding into her depths for a few moments, I stood on the side of the bed, pulling her thighs to me, stuffing a pillow under her ass, and she wrapped her ankles around my neck. Slow rhythmic thrusts built as she grew accustomed to my mass. Her big tits slowly rotated with every methodical ram at the end of my motion. Slow and slap, in and out.

I moved her up the bed, feeling the cold wet spot left on the pillow as my knee grazed over it and I climbed on top, picking up the pace inside of her. She dug her nails into my back, holding on as I bucked into her depths, moaning and shivering as an orgasm worked through her. I wrapped my arm around her, lifting her up and pulling her on top of me as I rolled to my back. A few little glides over my shaft and I slid right back in. She sat back, hands on her thighs, rocking back and forth onto me.

I squeezed her tits together, pinching her nipples and dragging my fingers lightly down her little belly. She leaned forward and hoisted herself up onto her feet, squatting over me, our mouths breathlessly competed for tongues as she bounced up and down. My arms stretched out and I pulled on her ass and her dense dangling tits swung in my face, and I began feeling myself on the verge of cumming. A pulse shot through my cock as I pulled her forward, allowing myself to slip out, and she sat back down on me as I shot a load between her ass cheeks. She pushed back into me, grinding it lightly through the duration of my climax.

We laid and cuddled a while, then she decided it was late and wanted to go, mentioning that her insides were tender. We cleaned up, got dressed and talked a bit in the kitchen. I held her in my arms and we began kissing again causing my meat to swell for round two.

"Can you handle it again?"

She smiled, reached down into my boxers and stroked me a few times, then turned and pulled me by the dick into the bedroom. Round two lasted way longer than the first, with us going through the positions we performed the first time, then ending an extended doggy style that slapped the headboard against the wall.

I held her thick hips, watching her big ass ripple with each of my pounding motions that smashed her head into the pillows. She gripped the open slats in my headboard, banging dents into the wall behind it. My brow poured with sweat despite the blasting ceiling fan and when she came again, I was right behind her. I pulled out, pressed my cock up her crack and rubbed into it as I spilled my load into the little divot of her back just above her ass. We cleaned up, laid there for 10 or 15 minutes and she left.

We talked a few more days and she said what happened with us just wasn't her and even though she had a great time, she just couldn't do the casual thing and it wasn't going to work long term. I apologized for, as she put it, "making it hard to sit for more than a few minutes" and we parted ways. I've been in touch with her here and there, checking in to see how she's doing and catching up as friends. She was definitely the type of girl I could see myself starting a relationship with and if she could separate herself from her faith a bit, in the least, she could be a top tier friend with benefits.

Date #19: Adalyn the Flake

Not that flaky people are anything out of the ordinary with online dating, but I wanted to mention Adalyn because she was just so fucking hot. I mean, her face wasn't the best, but she was damn cute. Her body though, it was a work of art. She had something for everyone.

33 years old, 5'7", athletic, tan, with shoulder length brown hair. She was a bit of a gym rat, but not excessively toned or muscly. She had big perky, "I know they look fake, but they're not" (direct quote) D cups, a narrow waist, and a meaty ass that jiggled just a little bit under her black slacks as we walked to the park on our date.

She was fun and carefree, and just crazy sexy with her squinty little eyes, adorable smile, and hair that looked just a little messy. Quite the contrast too, because her vibe was wild party girl, but she was a professional, rocking a pink silk blouse coming straight from her corporate gig downtown.

However, even before the actual date she was a bit flaky. I wasn't even sure we'd actually make it onto the date as we only sporadically messaged for a couple of weeks before things appeared to align and even then, it took two reschedules, and for me to return from my annual camping trip with friends to actually meet her. The date itself was ok, not too memorable outside of how fucking sexy she was, but we did some tequila shots, talked and laughed, and she had to call it an early night due to a work project she was about to button up. She definitely seemed interested, even initiating our mediocre goodbye kiss, but another couple of weeks of here and there messaging, I couldn't set up another date so I just let her drift away.

Date #20: Cassie the Old

I probably shouldn't mention this one, but what the hell, it's one that stuck out. Cassie was a cute little redhead in her early 40's. Her pictures were just ok, but she was fun, so I went out with her one night after work. As she approached, her petite body looked nice, but as she got closer, she just looked... old.

For the first time in my middle-aged dating life, I found a woman around my age completely unattractive to the point where I knew I couldn't kiss her because she looked her age. And she did. She didn't look older and she definitely didn't look younger. The entire dinner I sat there thinking, "she's so old." Her personality was great and we had some laughs, but I just couldn't do it.

After dinner she asked if I wanted to go to a bar she liked and I declined. I told her I wasn't feeling a connection and while she was nice, I wasn't interested in pursuing her further. She said she appreciated the honesty and mentioned, "at least you weren't an asshole like the last guy who told me I looked like I was 60." That cut deep.