The 50-First Dates Ch. 21-30

I ripped my shirt off and we embraced, her chest spilling around me as if I was to be taken into her body. She deftly unbuttoned my shorts, pushing them halfway down my ass and pulling my cock out of the top of my boxer briefs. We kissed and she stroked while I pawed on her perfectly round, plump ass over her tight jeans.

She continued pushing my shorts down, broke free from my kiss with, "Can I put you in my mouth?"

"That's the greatest question I've ever been asked." I smiled.

Sliding down the blanket, both of us on our sides, I lifted my hip so she could pull my shorts and boxers down to my knees. She sucked and slurped, like an expert, using her hands to mind 'the boys' and work my shaft. She made lots of noise, moans, ahh's and little hums as her head bobbed and twisted, while I pushed my shorts and boxers the rest of the way off. Another fantastic cocksucker.

With a slurp and a pop, she climbed back up to me and I noticed upon her return, she had somehow peeled herself out of her jeans and underwear. My hands gripped her flowing hips and she guided my tip between her legs, over her full, but sparse muff along her moistened slit.

"God, I want you to fuck me."

"I don't have any condoms."

"We don't need condoms."

"You're on birth control?"

"Just pull out, I trust you."

The record skipped. This was fun and all, and I was totally turned on to this point, but her recklessness was an immediate turn off and I had gotten way ahead of myself. I've taken some risks, and I guess was ready to take another one in this moment, but this was too much. In the moment it felt like she's done this before, and a lot.

The other women I've fucked up to this point were all good girls to a certain degree. Women who hadn't been super active sexually, especially recently. I guess I'm just taking their word for it because you never really know, but I have no reason not to believe them. With her actions, however, it was obvious she's not afraid to move very quickly, unprotected, with a stranger.

"Maybe we shouldn't rush."

"No?"

"Yeah, this is going a little fast. I told you, I'm not a hookup guy."

"It's not a hookup if we do it again. You would want to do it again, wouldn't you?"

"Yeah, sure." I uncomfortably lied.

"Would you rather just come home with me?"

"Aren't your sons (teenagers) home?"

"Yeah, but they're just gaming and they never notice when I come and go."

She obviously had done this before and I was totally turned off at this point, my dick started going soft in her hands.

"I dunno, I'm kind of tired. I think this is enough for tonight."

"Uhh... Yeah... Ok," she panned.

She stood up, showing her thickness in the moonlight and staring up at her, I questioned if I shouldn't just say "fuck it" and run with it. She looked really fun naked. Bigger heads prevailed and as she slipped back into her thong and wrestled her enormous tits into her bra, I stepped into my shorts, pulled on my shirt, and stuffed my boxers into the bag.

Once she was reclothed, we packed everything up and headed back to our cars. I gave her a kiss, she tried to get more aggressive, once again grabbing onto my crotch, but I just laughed, stepped back, and wished her a good night. When I got home, I sent her a text thanking her for a nice night and saying I wasn't sure we were a good fit. She questioned it and I just said I didn't want to move so fast, but now that we had, there was no turning back. It was the nicest way to say I was worried that she was a hoe I could think of and it worked. She wished me luck and just like that, on to the next one.

Date #29: Tara the Girlfriend

A whole lot of what I thought were my dealbreakers went out the window with this one and I learned my lesson (maybe). I was good at keeping distance emotionally at this point, but Tara just fell right into place. She was really pretty despite her terrible pictures, the banter was solid, and just as I was getting ready to ask her on a date, she disappeared. Her profile was there, she didn't delete me, but her messaging just stopped. Happens a lot, so I didn't think much of it.

Almost a week later she sent a message with her phone number, 'Sorry, my dad died and I've been busy with that. Give me a call sometime...'

I really had no idea what to do with that, but after looking at it for almost 24 hours, I threw my hands up and gave her a call. As it turns out, she was not close with her father, but his death was still obviously a big hit for her. She was dealing with a lot of family bullshit and already lonely from her failed, abusive marriage, and really just needed some support.

She was adamant about being serious and with her growing business and four children, she had little time. Honestly, when I first started talking to her that night, I almost ended it right away because of those things, but she was vulnerable and I did feel a connection the more we talked, so I just let it go and pushed forward.

We ended up talking for several hours, her somber tone shifting to giggles and laughs as I joked and teased with her. We really hit it off. I really liked her and by the end of it, we had plans to go out that weekend.

Agreeing on one of my favorite date areas with lots of nice little restaurants, the jazz lounge for drinks, and those lakeside benches where I've shared so many first kisses. She had to push back our meetup time last minute and then ended up almost 15 minutes late beyond that. It wasn't a big deal, especially after I saw her.

She gave off the vibe of all the girls in high school I always had a crush on. Early 40's, 5'7", very lean, somewhat athletic frame (135lbs), blond dye job pulled up in a clip, huge beautiful blue eyes, and the girl next door cheerleader smile. My inner teenage self was climbing the fucking walls looking at her. Her cute little tits, braless under her black spaghetti strap shirt, and the dark tan skin definitely helped. Plus, the loose white cutoff jean shorts that highlighted her long, smooth legs, gave me lots of ideas.

We ate dinner at a German restaurant, sipped beers, and the conversation just kept rolling. We fit in so many ways and I was wildly attracted to her, so I allowed myself to overlook her trauma dumping tendencies. From dinner we hit the jazz lounge for a quick drink, then ventured waterside and cuddled on a bench swing.

"What are you thinking?"

Her comment came from nowhere as we were ebbing and flowing perfectly in conversation, so I knew what she was really thinking.

"I'm thinking about how you want to kiss me right now."

"You think so?"

"Show me."

She blushed, grinned, ran her fingers into my beard and lightly kissed my lips.

"Is that all you want?" I teased.

She giggled, wrapped her arms around my neck and tongued into my mouth. Great kisser. A little bit of making out and my hand feeling up her taut body, tracing her ribs and eventually squeezing hard on her perky A cups as the passion skyrocketed.

A big exhale as my hand flirted under the frayed edges of her shorts up her thigh, teasing the crease of her cute little butt when she stood up and climbed on top of me. Both of my hands went under the sides of her shirt, feeling her firm body, back down, then holding her hips and pressing my thumbs under her protruding hip bones just above her shorts peeking from under her shirt. She rocked back and forth, her thick long hair falling from the clip and covering our faces as her crotch massaged my hardening dick.

"What do you want to do?"

"I want to take you home and fuck your brains out, but this is a first date and I'm a gentleman."

"Do you want a second date then?"

"Obviously."

We kissed a bit more and I could tell she was uncomfortable with her knees pressed into the metal slats of the bench, so I decided to call it a night. Plenty of time for more of that later.

Back at our vehicles, we continued making out and it was getting late. With nobody around, and a little misting rain starting, I had my hands just barely filled with her cute little butt which gave me ideas.

"Want to make out in my truck?"

She laughed, "Like high school?"

"Yeah, just like high school."

I opened the back door for her and she climbed in, sticking that tiny handful of an ass right in my face, her shorts revealing small lines of white hidden under her bronzed tan cheeks. I jumped in behind her and the clothes began falling off. Unfortunately, we weren't young anymore, so it was quite uncomfortable. My truck, while comfortable to sit, wasn't exactly laid out for sex. Maybe I needed to invest in a van.

Just before we hit the underwear, I made the call that we should pick this up another time. She agreed and we were off, another date a couple days later on the books.

She, like me, was an avid DIY'er and often talked about looking for someone to make the boring stuff in life fun and not so monotonous. We talked a lot about the projects we had worked on, shared a bunch of pictures, and laughed about our love for the home improvement stores. So, when planning that second date, I decided to do something a little odd, but it turned out amazing. Dinner, then Home Depot.

We talked so much at dinner it clearly annoyed the server. Almost 3 hours at dinner in total, it took us at least a half hour to even look at the menu. Seemed like a good sign. I teased her throughout about a big surprise I had for her and she joked that she was down for anything, unless it involved ending up as a skin suit.

I paid the check, noting to myself that Home Depot was closing in an hour, but of course our dinner spot was right across the street. I drove her over and she lit up, "this is the cutest thing I've ever heard of for a date!"

We felt like a real couple as we walked in and as such, I naturally held her hand. Fingers intertwined, we meandered up and down the aisles, picking out bathroom tiles, flooring, fixtures, and everything for our individual dream homes. We had identical tastes, but different perspectives. She picked out things I wouldn't have, and I did the same with her, but we both would raise our eyebrows with a "huh, that is really nice" every time.

From there we hit a little bar I had scoped out in the plaza next door. The place was hopping with regulars and we were 'fresh meat.' We were cornered by several drunk people trying to chat us up, friendly enough, but as I sat there playing with her hands on the table everyone just fawned over how cute of a couple we were. It was fast, but felt perfect.

Tammie was one of the drunks that plopped herself down at our table and talked to us. She asked how long we've been together, was surprised it was only a second date, and went on and on about how she could tell we were in love. Funny enough, Tammie was pretty good looking and I saw her on one of the apps months later. I really thought about matching with her, but she was kind of annoying so I didn't.

After finishing our drinks, we went back to my truck and Tara climbed all over me again. We made out hot and heavy in my front seat and I made her cum a couple of times with my fingers as the windows fogged up. If we weren't so far away and it wasn't so late, I would have taken her home immediately that night.

Taking her back to her car, we shared a kiss and I had a girlfriend. It just felt so right. It wasn't the super crazy "wow" I had with Tina, but it was just natural and comfortable like with Lisa was before. We felt like we'd known each other forever and we fit like perfect puzzle pieces.

She actually mentioned it after sitting down in her car.

"Am I crazy or does this feel right?"

"You're not crazy."

"Would it be crazy if I deleted the app?"

"After two dates? Maybe a little."

"I'm ready."

"It seems fast though, but I can't deny it feels good."

"I'm deleting it. You don't have to if you're not ready, but you already make me so happy."

She pulled her phone out, opened the app, deleted her account, then uninstalled the app.

"Are you freaked out?"

"Maybe a little. It's fast. I've had bad experiences moving fast."

"I get it. Don't worry. I'm not in love with you or anything, but you're super sweet and I can tell you'll treat me well. Just doesn't seem necessary to keep talking to other people."

"I feel that too. I just don't want to dive off the cliff into something really serious right now."

"Understood. That's ok. I'm just not going to see anyone else and want to see where this goes."

"Honestly, I don't feel like seeing anyone else either."

"Good."

"Yeah, I think it is."

We kissed and parted ways, continuing our daily memes, gifs, texts, and evening phone calls for several weeks trying to get our schedules to align. We were both very busy and she had to cancel a few dates because of her business. Finally, one night out of the blue, she asked if I was busy.

'My kids have been pushing me to go out with you again and they're settled in for the evening, my oldest isn't going out and said she'd take care of everything so I can sneak out after I tuck my little one in.'

I offered to go out, but she declined saying she just wanted to spend time with me, maybe watch a movie. And with that, I stormed around the house cleaning the little bit of mess that had grown that week, lighting candles, and she arrived an hour later with a bottle of wine wearing the "comfy clothes" we both agreed on. Me, in a t-shirt and athletic shorts, her in a baby t, super short gym shorts, and hair up in a messy bun.

It was a nice night, so we sat on my patio overlooking the pool, cuddling and sipping wine. We talked about life and held hands, not going straight sexual, but rather enjoying a nice romantic evening. Spending a couple of hours just enjoying each other's company without pure lust in our loins was really, really nice. It felt safe and secure, cute and innocent.

"I'm getting tired. I think the wine's getting to me."

"Are you ok to drive?"

"Maybe, but can we just lay down a bit?"

"Absolutely."

We venture to my bedroom, pulled back the comforter and snuggled together. As we spooned, I lightly caressed her silky arm and nuzzling the whispy hairs behind her ear, softly kissing her neck and shoulder. I snuck my arm under her pillow, wrapping it around to her chest and she locked her fingers with mine. I continued kissing her neck and dragged my fingers down her side, over her hip and tickled the velveting skin on her thigh.

"Mmmm" she pressed her ass against me, slightly shifting her hips back and forth.

My fingertips danced around to her butt, spreading it with a squeeze so I could press my thickening member to greet her warm center, then running my fingers to the front, under her shorts and onto her soft panties, glued to her puffy labia.

"MMMMMmmmm" her shifting hips rocked up and down over my granite cock as I toyed into her underwear and onto her baby smooth lips.

Pulling my hand to her little chest, she squeezed it, inviting me onto her adorable tits. Massaging between them, I felt her hand reach back and push down my shorts, straining to reach my cock. Removing my dripping fingers from her swollen box, I pulled my shorts down and kicked them off, rolling back into her as she arched her back, and directed my piece up and down, teasing it inside her shorts and onto her soaked through panties.

Lifting her leg, she held me between her thighs and pinched hard, stroking me slowly with her hip motions. Turning to kiss me, our tongues fluttered while she twisted her body to maintain her grip and kissing me deeply.

I began pushing down her shorts and panties. She writhed and wriggled, setting my cock free and allowing her shorts to drop to the point where I could use my toes to pull them the rest of the way off. Pressing back against me, she reached down and guided my cock into her hot little hole. I leaned back, pushing myself fully inside and tearing my shirt over my head. She worked back and forth and I ran my arm back under her neck, then down her shirt in the front, and with my other hand, drove up the front over her stomach onto her chest.

Clamping down on her tiny perkies and holding her heaving ribs, I worked along with her motions in and out, holding her tightly and sucking her earlobe. It was slow and passionate, sexy, hot... deep.

"Get on top of me, I want to feel you."

Flashes of Lucy wanting to feel my weight ran through me.

I pulled out, grabbing her hip and pressing her ass back to the bed, kneeling up in front of her and spreading her long legs wide. As I stared down at her, she peeled her shirt off and unveiled her sexy, toned, almost skinny body. She wasn't my normal type, but was incredibly beautiful naked. Slight hint of abs, flexing ribs with each breath, prominent hip bones and clavicles that sunk as she moved. Cheery little tan titties, tiny nips and areolas, a surprisingly plump pussy, completely bald less a thin little stripe of trimmed hair just above it.

I rocked myself back and forth, her fat little pussy wrapping around my girth like a hotdog at the ballgame. I slid the tip into her steamy canal, burning hot and dripping wet. I teased it in and out, watching her firm body flex to receive me. In a little, then out. Back in a little deeper, then out. Deeper, almost out, then back in down to the balls.

"OH! Oh shit!" she chirped as she gushed the world's fastest orgasm.

Drawing her knees together and clasping her legs to my chest, I leaned forward with her feet wrapping around my head and ground myself into her.

"I LOVE how it stretches me."

Still slowly working her, I was strong and forceful, while remaining methodical. In, press hard, out slowly, back in. Repeat, trying to give her as much of a stretch as possible with every spiraling thrust at the end of each stroke.

She trembled beneath me, creaming another orgasmic contraction moments later.

"Fuck me hard." She purred.

I placed my thumbs under the backs of her knees and pushed them down to her shoulders hard, holding my entire mass above her and pinning her into the mattress. Long, slow slaps turned into rapid fire jackhammers as she squealed beneath me.

"Fuck, FUCK, FUUUUUCK! I'm cumming again, Oh God, I'm cumming!"

Full on body shivers bordering the alarming rocked through her and she scraped her nails down my fully flexed arms, leaving long raised marks that nearly drew blood. Unrelenting, I clapped into her, feeling my pubis tinge with the stinging pain of my aggression.

"I'm still cumming! Fuck me Jack, fuck me! Fuuuuuuuuuuuuuuuuck meee!"

The sloppy wet sounds of skin echoed the room as the headboard began smacking against the wall. The sweat poured off my forehead and dripped to her chest.

"Let me on top!" she moaned breathlessly.

Exhausted, I collapsed off to her side and she aggressively stood over me, stooped down delicately holding my throbbing cock with her perfectly manicured French tips and directing me inside of her. Crouched down over me, she dug her nails into my chest, leaving deep marks tinged with blood, then bounced up and down perfectly on my cock, taking it all the way to the base and nearly letting it fall out with every rebound. She'd pause every few seconds of her rapid bucking, dropping her full weight down and grinding hard back and forth, feeling my stretch and bending me inside of her.

Her lean body looked glorious as her messy bun began falling off to the side and unraveling, her little tits spinning in their slight hang and stomach sunk in on the sides as her core was fully engaged. She fucked my dick like she was a starving man on death row and it was her last meal. I've never had anyone so aggressively fuck me like that and I was dying to cum.

"I want to fuck you from behind, lay down!" I commanded.

"I want to feel you cum in me" she panted as she crawled off onto all fours.