The 50-First Dates Ch. 21-30

It got to the point in which I was really twisting them, so I pulled down the top of her dress and began kissing her upper chest. She helped slide her arms out of the top of her dress and pushed down her bra, exposing her long pink nipples and tiny areolas, red from my advances under the bright parking lot light. I nibbled and licked back and forth, gently teasing with my teeth, flicking my tongue, and biting with increasing firmness. The harder I went, the more vocal she got. Eventually, I was going very hard on the and thinking to myself, "I'm really going to hurt her."

But, I didn't. She loved it. A solid 15 minutes of nipple play and I could feel how raw they were under my tongue. I helped her pull herself together and we kissed a bit more.

"I had no idea I liked that."

"You DID like that."

"I liked it a lot."

"I'm glad to teach you something."

"You've been with a lot of women, haven't you?"

"Define a lot."

"More than... 10?"

I laughed, "Yes, more than 10."

"How many more?"

"Honestly, I'm not entirely sure. I did a lot of things in my past."

"Like 100?"

I actually snorted, "No, nowhere near 100. Maybe 20, or 25. I really don't know. I don't exactly have a running tally."

"So 25 is what it takes to learn all those skills, huh?"

"Well, I said I've been with 25, that doesn't mean I haven't just played with others."

At that point she just smiled, said she had to go, and after another little kiss, she got in her car and left.

We talked that week a bit more and I expressed to her that I was concerned about her being so inexperienced. She said she had concerns about me being a player, not emotionally available, but was eager to learn some things. We talked a lot about sex and she had ideas she had heard from other people, but never actually experienced herself. One she was most curious about was a creampie.

I described it as best as I could and she was intrigued. We discussed birth control and she assured me she had been on it since her last breakup, was rigorously tested after her tragic "date", noting that she wanted to explore her sexuality more.

Our second date didn't play out so well. We ate at a riverside seafood place and she used all her counselling skills to dig deep into my past, into my psyche. She said she understood why I was the way I was, which felt like a dig, but she assured me it was not. She lamented my ex and expressed more concerns about my active dating life.

I was, and still am tested after each new partner, but the bonehead I am, I didn't get what she was really talking about. It wasn't STD's she was worried about; it was her feelings. I hadn't been clear enough about my hesitancy to get into anything committed and unbeknownst to me, the idea of that turned her off. It wasn't fully transparent on either side and my impression was, she was just turned off that I wanted something more casual. That date ended without a kiss and we parted ways. I didn't expect to hear from her again.

A few days later we she reached out and invited me over. This is something that happens from time to time. Not on the same page about something serious, but I'm fun and comfortable, not completely terrible with my touch, so they circle back around and are willing to keep the feelings out - have fun, hang out, and do adult things with each other.

I arrived at her apartment with wine, we watched part of My Cousin Vinny, killed the bottle, and retired to her bedroom. The first time wasn't that great, honestly. She was insanely tight and her pasty freckled body was quite sexy, but she never let herself go. She was very reserved. She wanted to try things, different positions, but she couldn't totally get into it. She was stuck in her own head.

One and done that night; I didn't want to try to write the whole book on sex in one evening. We continued talking and I invited her to my place a couple weeks later. Another bottle of red, the other half of My Cousin Vinny and she went to the bathroom flipping her dress in the back to tease me as she disappeared into the hallway, showing me her cute butt and sexy black cheeky cotton panties.

I waited for her on the couch and invited her on top of me, quickly peeling the dress off and devouring her body with a strong touch.

"Let's go to your bedroom."

Don't have to tell me twice. She giggled and pranced into my room, flopping herself onto my bed. I pulled my shirt off and dropped my shorts, pressing myself down on top of her as we kissed. She held my shoulders and I rubbed my sheathed girth into her pussy-soaked panties, holding myself up with one arm, leaving myself free to pull down her bra and pinch her hard nipples. Her hands shot down to my waistband and stretched to push it down.

I slid down her body biting hard on one nipple, then lightly licking the other, kissed down her stomach and pulled her panties off. Her cascading pussy was covered in sparse, straight bright orange hair that was quite soft to the touch. She had the kind of muff that never needed trimmed. Soft hairs never grew more than an inch and never came close to becoming a concern along the bikini line.

I breathed in her scent, the silky hairs tickling my nose as my tongue swept up and down, parting the hair and finding the slickness inside. She whimpered and moaned as I tongued around her opening, sucking her hard clit and probing my tongue in and out of her lightly. A full suck on her pussy with my tongue flicking her little pea sized clit had her thighs slam hard against my ears. I reached up from rubbing her pubis and pulled on her nipples. She crushed my head in a rapid secession of orgasms.

"I want to suck your dick."

I stood up, my drooling hard cock bouncing as I wiped her froth from my beard. She sat on the edge of the bed and leaned forward, taking me between her lips and grating me with her teeth.

"Careful. Open wider."

The teeth subsided.

"Don't swallow your spit, cover me with it."

The drool ran down my balls.

"Suck harder, now you can swallow."

One loud slurp and I was in her throat.

"Use your hand."

I grabbed her hand and placed it on the base of my shaft, wrapping her fingers around and starting her in a twist and tug.

"Fuck yes."

I made a pretty good cocksucker out of her.

With a string of saliva connecting us as I pushed her back, I gripped my slimy member and directed her up on the bed. Climbing on top, I sat back on my feet and teased my purple helmet up and down her steamy pussy, guiding it in slowly.

Her crazy tight little pussy was on fire. In and out, deeper and deeper, I picked up the pace and pinned her knees back to her chest.

"Oh Jack... Yes Jack!"

Buried deep within her vice grip, I felt the tinge of climax as my rhythm now a full pummel.

"I'm going to cum."

"Cum in me."

"Cum where?"

"Cum inside of me."

"Inside of what?"

"Cum in my pussy!"

"Who's pussy?"

"My pussy!"

"WHO'S PUSSY!?"

"MY PUSSY!"

"THAT'S MY LITTLE PUSSY!!!"

"CUM IN YOUR LITTLE PUSSY JACK!!!!"

I drove all the way to the bottom and exploded into her depths. Ball draining flex after ball draining flex, I pumped in a week's worth of no fap and filled her up.

"Oh my God, I really felt that!"

"It was a good one."

"No, I mean, I REALLY felt it come out."

"Yeah, it was a good one."

We laid there chatting and covered in sex for maybe a half hour before dozing off. I woke up a bit later, chilled and still a bit sticky. Looking her over, I began touching myself and brought Mr Happy back to the party.

Stroking my rod, I woke her up with light little sucks on her nipples. She directed me back and forth between them and I demanded to taste her again.

"Ride my face."

Awkward at first, I moved her onto her knees, straddling my head and holding on to the headboard in front of her. Staring up at her body, my hands travelled as far as they could, up and down as she planted herself on my mouth. I really loved her body. So pasty, freckly, sexy. Soft and firm, attractive by anyone's terms.

She smashed my face hard and with my mouth full and occupied, I couldn't tell her to back off. My attempts to lift her from her ass completely failed. I felt my teeth gnawing her pussy, not that she seemed to mind. I brought her to climax and she left a snail trail down my body onto my erect meat.

Slathered in her heated drippings, she took me in with zero effort. She clumsily tried to ride me, obviously not knowing what she was doing. She refused to rise up and down, eventually following some of the direction of my hands on her hips and rocking back and forth deep inside.

"I want to try doggie, I've never done it before."

"Head down ass up" I commanded as she dismounted me.

"What?"

"Just bend over."

On all fours, she turned to look at me and I pushed down between her shoulder blades, smashing her head into the pillow.

"Keep that ass up."

Tugging myself, I leaned forward and licked her pussy all the way up her ass crack, bit a cheek, then kneeled my way forward and pushed myself inside. I stared down and watched her bright pink pussy stretching out as I pulled back, leaving a ring of cream around the base. Squeezing hard on her hips, I pounded into her, bouncing her into the headboard, clanking it against the wall.

Her first screaming orgasm ever echoed throughout my house as I kept crushing her depths. She reached back and shoved onto my stomach, forcing me out and curling up into a ball at the top of the bed, heaving and trembling.

"I... I can't... It's too much."

"Are you ok?"

"More than ok. It's just too sensitive. I can't handle it like that right now."

"I can go slow."

"Ok."

She resumed the position and I went back to work, more slowly and methodically, tickling my fingertips up and down her back, then randomly slapping her ass.

"I love how you're soft and rough at the same time!"

"Mmmhmm."

"I really like it."

"Lay flat on your stomach."

She was confused, so I pulled a pillow and stuffed it under her, directing her to lay flat beneath me with her cute butt perked up at a slight angle. I ran my thumb down her ass and inside of her spent little pussy, handling myself and working her back up.

I spit in my hand, smeared it over my straining helmet, pinched her cheeks apart and pushed myself inside again. I laid on top of her sweet perky ass, grinding myself deep inside and biting her neck. Slow and sexy, her quivering broken twat burning for every inch.

A few minutes later I came again, dumping a half load as far in as I could push, loving how her cool backside felt against my pubis. She pushed back into me, squeezing her legs together as I throbbed into her cervix.

We cuddled for a minute and fell asleep again, both waking up again in the wee hours and she went home. Things seemed great following that. I thought we had a great little friend with benefits thing going on and I had been perfectly clear. Through our chats I mentioned going out with another girl and she blew up.

She got very nasty, calling me names, and insulting me. I called her out on it, told her I it seemed like we needed a break from whatever it was we were doing and the vitriol continued to pour from her. She said I was manipulative, while at the same time telling me she wanted to work me through it and her clear insults weren't actually insults at all. She leveraged her past, touting abuse from her childhood, almost as if she blamed me for every bad thing in her life that had happened to her. Over the span of a dozen or so texts, she went from rage, to devastation, to sweetness and back. She was actually attempting to manipulate me, projecting herself through her commentary about me, like Babe Ruth pointing his bat to center field.

I attempted to reason with her and continue to explain things, but she kept with the name calling to the point I finally told her that I wouldn't be responding to her again. Her response was to go full rage victim, and I blocked her. Looking back, I definitely needed to define things more up front, especially given her lack of relationship experience, and I'm certain to be that way now, but at the time I honestly thought we were on the same page. Despite really feeling bad about the miscommunication, I definitely dodged a bullet with her. Had it gone on any longer, the end, regardless of if we both totally started on the same page or not, probably would have been much worse.

Date #26: Nicca the Phony

A real fun one. Nicca's profile said she was 41 and her pictures were pretty well filtered, but you could see she was attractive and had some serious curves. A little bit of a risk to run with it, but I had a free spot in my schedule to fit and she was available.

I took her to the same spot I took June and she showed up looking pretty good. Walking to greet her in her shrink-wrapped jeans and sweater, the closer I got, the more I knew I was not into her. Tall, pretty, dark skinned Hispanic gal with a jet-black bob, huge fake tits and a big fake ass. I hate that and she looked more natural in her pictures, though I did suspect a boob job even then.

She gave major "fuck me" vibes over dinner and I had fun with it, flirting and getting a little tipsy with some shots. Right off the bat she said she was down for something less serious, but did mention she wanted a few dates to get comfortable. She was fun and after several "meh" dates post Maura, I figured what the hell. Any port in a storm.

After dinner we walked to the lake and sat on a bench to chat. I put my arm around her and got more comfortable. We started to broach the subject of sex and she made a confession.

"You know I'm not 41, right?"

"Uh... how old are you?"

"45, about to be 46."

"Ok, that's weird."

"And my name's not Nicca."

"Oh really?"

"It's [redacted]."

"Interesting."

"Yeah, I'm worried about stalkers so I change some things so people can't find me."

"Or because you're hiding something," I groaned with an uncomfortable chuckle.

"No, I have nothing to hide."

"Ok."

That kind of sealed the deal for me. I guess I understand the thought process, but with fake tits, fake ass, a fake name, and a fake age... I'm out. We kept talking a bit and I decided to call it a night. On the walk back, she was talking about how she wanted something to start casual and get serious - "to build someone."

"Build... WITH someone?"

"In part."

"What part?"

"Obviously we're going to grow together, but I like to look for potential and help people grow individually."

"How so?"

"Well, I did notice in your profile that you're a little overweight, and I love the gym, so I figured we could work on that."

L. O. L.

This weirdo lied to me from the jump and wanted to get with me so she could help me get buff. What in the crazy fuck is going on in this world?

I gave her a hug at her car and told her I didn't feel enough of a spark, wished her well and sent her packing. Good grief. A few weeks later I saw her profile on another app, with another name, and another age - neither of which were accurate. Or maybe they were. Who the fuck knows?

Date #27: Natasha the Stoic

My first foray into Eastern Bloc women. Natasha was 42 and model beautiful. 5'6" wispy brown hair, big pretty brown eyes, and the classic timeless beauty women from that area of the world are known for. She was lean, fit, and had a perfect hourglass shape.

We went on a couple of dates, kissed a little, and she disappeared. The entire time we talked, it was impossible to get a read on her. She'd smile and laugh, but was never overtly flirty. She challenged me on just about everything I said, not in an aggressive mean way, more of a "trying to see if this all holds up" sort of way.

It was strange. I never knew where she stood, but she was receptive to my advances. Still, I didn't get the feeling like she was actually in to me. She was really hot though, so I went on those dates to see if it could go somewhere. It's possible she was using me for attention or something like that, but it's also possible she was interested and I wasn't aggressive enough. Really hard to say because I could not at all tell what was going on between her ears. I have a good radar for these things and win some, lose some, but she's just one I could quite figure out. Turns out, several experiences later, that's kind of par for the course with women from that part of the world.

Date #28: Jane the Easy

Like so many others before, and after, Jane was a recent divorcee. She was fucked over by her husband, a theme that repeats so much that I question anyone who says "it just didn't work out" or "we grew apart." Maybe I'm cynical, but it seems pretty clear at this point that someone saying that is actually hiding something. They fucked up. They were probably a cheater. Marriages just don't really end because people grew apart. You live with growing apart, you work on growing apart - especially when kids are involved. Perhaps, that's just fantasy. I figure that's the way it's supposed to be. On the other hand, you don't live with cheating, and you can't work with cheaters. They're simply not trustworthy, honorable people.

Jane was cute enough on her profile, very short, and had really big tits. She was my age, 5' even, something crazy like H cups, and just a little bit chubby. She was certainly very top heavy, but still had a good booty according to her pictures. She was open on her profile that she wasn't looking for anything serious, but also wasn't looking for a hookup - right up my alley.

I met Jane at a little seafood spot on the intercoastal and her representation on her profile was perfectly accurate. A light splash of freckles littered her cute, round face, and ample cleavage. Long, straight pretty brown hair with just a tinge of natural red. She had light brown eyes, not quite hazel, and a charming laugh. She was a little meatball of a woman - you couldn't call her fat, but she wasn't exactly petite. She had what I would consider a fun body. Unless you're a boob guy, her body wouldn't necessarily wow you, but nobody could say she wasn't attractive. Her body just seemed built for sex.

We ate dinner and drank beers watching the sunset and chatting. She dumped all her trauma about her marriage - the cheating, the lies, the manipulation, the vindictive nature of a narcissistic partner when they don't get their way. Same tune, different drum. I've heard this 1,000 times before and frankly, lived it a bit myself. What a wild, terrifying world we live in.

After dinner, we went to my truck and grabbed my patented beach bag - blankets, wine, and two plastic cups. As I could tell from Google Maps, this particular beach was very, very private. It was pretty much dedicated to the restaurant as it was only a couple of hundred yards wide, with big overgrowths of mangroves on either side and thick foliage separating it from any public view. The sand was nice and there was a little public parking access point, but nothing else was really around, so we ended up completely alone under the bright moon.

Even though wine really wasn't her thing, she had a glass (plastic cup) with me and we chatted and flirted. I asked if she wanted another glass and she said she wanted something else.

"I'd rather just kiss you."

I smirked, scooted myself closer, and began kissing her. Nothing memorable about her kissing technique, but she liked it and started getting very aggressive. Straight for my cock, her hands rubbed up and down my crotch, getting me hard very quickly.

My hand found its way up her sweater and immediately unclasped the 6 clips holding back her massive chest. She wasted no time, sitting up and peeling that sweater off with the bra, dropping her massive tits out into the breezy air. Her body was even better out of clothes. Those massive milkers were surprisingly perky for being so big and being attached to a 40-year-old mom. Huge, firm, with areolas the size of that ring a can of beer leaves on the table and big nipples like a stack of 10 dimes, light brown against her pale skin.