The 50-First Dates Ch. 31-40

She barely picked at her food, but when the band took a break, our conversation improved significantly. We talked about good dates, bad dates, and downed a few beers. While we were talking, I really felt like it wasn't going anywhere and I was getting bored. I decided to play a game where we looked around at all the other couples and guessed how long they had been together.

We both agreed the couple at the bar had been dating a while, but weren't quite serious yet and the couple behind us was on one of their first dates. The way that girl was looking at her man would be the envy of any couple. Deciding to test her, I said we should approach each couple and report back on our findings.

Turns out, we were both very wrong. My couple at the bar had been together 18 months and just moved in together, actively talking wedding plans as they had their drinks. Her couple had actually been together for 4 years and had a small child together. It was a fun thing I might have to incorporate in future dates.

Overall, she was just a little weird. Nothing really stood out to talk about, but she had an awkward energy that her looks just couldn't overcome. She appeared confident in how she carried herself, but her inner energy gave me insecure vibes. It was a very odd combination.

Just as we were wrapping things up, the weather turned and storm rolled in quickly. We stopped at the bathroom on our way out and the sky opened up, dumping buckets. We stood at the entrance, hoping it would slow down, but after a few minutes it was obvious that it wasn't.

I said my goodbye and went for a hug noting on the way in she obviously was looking to kiss me. The gentleman I am, I obliged. Absolutely nothing dynamic or exciting, despite her incredibly sexy mouth. Though, running my hands up and down her taut sides, grazing the top of her cute little butt, did get junior stirring a bit. Breaking away with a smile, we took off running through the parking lot and to her car. Another quick kiss and I darted to my truck.

She continued to text me and while I think she would have been fun to play with, I really wasn't feeling it. Very quickly after the date she began talking a little too serious for my liking and I told her that since she hadn't had much dating experience beyond her last relationship, she should go out and date more. Again, she said she was only interested in me and I played it off, ultimately telling her I was going to see other people.

Date #38: Heather the Hut

I shouldn't be this harsh with the nickname, but I was fatfished once again. Heather was a teacher in her late 20's and beautiful. She had one half body and one full body pic on her profile and while she looked thick, she ended up being quite fat.

She was really fun, maybe a little goofy, but we vibed immediately after matching. She had the blond hair, blue eye thing going on and a gorgeous smile. While I was a little suspicious of her pics given the angles, I figured if she's thick we're good, so I gave it a shot.

The plan was to meet at a restaurant near the beach and play mini-golf next door. Weather was rolling in hard as I approached, so we decided to wait on dinner and do the putt-putt thing first. I parked right next to her, noting that through the tinted glass, she was really holding up. I got excited.

Then she stepped out.

At 5'2", she got out of the car and my heart sank. She didn't have a terrible shape, but she was plenty big. I like some hips and ass, but she had well more than what I was ready to sign up for. I gave her a hug, her massive tits felt nice against my stomach so I started thinking maybe a friend's with benefits thing, forgetting all about the Liz situations so many months before.

After dominating her in our golf game, the weather was starting to whip up so we jaunted over to the little brewery for dinner. We had really good banter going and I was so focused on how naturally pretty she was, I started to wonder if I was being too shallow. She was a ton of fun and just plain gorgeous sitting across the table.

Of course, that didn't last as when we got up to leave, I was reminded of the full picture. When we got to her car, she was immediately angling for a second date. I told her that while I was attracted to her, I didn't feel a deeper connection growing. She questioned how I could be simultaneously attracted, but not enough and rather than hurt her feelings I gave her an honest, yet tactical response.

"Honestly, you're beautiful. I don't know what it is, but it's just not there for me for some reason. I had fun, but I don't see this going anywhere serious."

"But you do see it going somewhere... unserious?"

I laughed, "Sure. I'm totally down to make out with you right now and maybe more sometime."

My standard 'friends with benefits pitch' was taking form.

"Oh god, I don't even kiss on the first date!" she smiled as she blushed.

"Well, I'm not saying let's go hook up right now."

"Kinda seems like it."

"Nah, not at all. I mean, I'm open to a more casual situation, but I'm not looking to just hit and quit."

"Oh, so friends with benefits?"

"If you're open to that."

"That's not really what I'm looking for."

"I understand. I'm not really either, but I'm open to it."

"I'm not."

"Ok, fair enough."

I gave her a hug, wished her luck, and was on my way.

Date #39: Zahra the Motivational

Tall, late 30's mom, with a sexy curvy body and very strong features, Zahra was a hot Middle Eastern transplant who escaped a conflict zone with her family in her elementary years. She was sharp as a tack, had massive tits, and always had an interesting question or thoughtful statement to make. She was sexy.

Immediately we hit it off on an intellectual level and she wasn't too bad with humor either. We met late one evening for sushi after weeks of trying to get together. I make it a habit to get to my dates early to ensure the girl doesn't have to wait, but she was one of the few that actually beat me.

Walking up to meet her out front of the spot, I noticed her full figure and long straight, almost black hair and move star level makeup. She was quite attractive and had meat in all the right places. In a rare turn, she actually drove the conversation as we split a bottle of wine.

It was different, but not at all uncomfortable as we delved into geopolitics and philosophy as if we were intellectual colleagues sharing dinner after a long day of teaching at an Ivy League university. Her little dashes of humor definitely drew me in, but more than anything, I was impressed with her brain. And her drive.

Too much drive.

I enjoy a pretty leisurely life. I work, I have hobbies, but I like to fuck off and do nothing sometimes. Zahra had none of that. The lists of clubs and events and online courses and constant run run run lifestyle was exhausting just hearing about it. From her high-level engineering career to her book writing and goal to be a motivational speaker, I didn't find our lifestyles to be a good fit. She disagreed.

The quick date was nice and all, but deep inside I knew I'd be forcing it with her. At the time though, I was so intrigued by her intelligence and she was sexy, so I went ahead and kissed her when I walked to her to her car. She was a great kisser and her firm thickness really turned me on.

We made out a bit and her conservative side came out as my hands began to roam a little. She didn't stop me or anything, but I could feel her excitement grow to nervousness as it progressed so I eased off and excused myself for the night.

Texting back and forth for a while, I was focused on the schedules, but the longer it went on I realized even if our schedules were perfectly aligned, it wasn't going to work. She was brilliant. She was sexy. She had so much going on it was a little intimidating, but frankly, there just wasn't any there, there. After answering another very clever and deep question I had grown accustomed to fielding from her, I asked her if she thought it was going anywhere and she said she wasn't sure. I took that as an opportunity to break things off - 'if we both aren't sure after talking for almost two months, I think we know the answer deep down.'

Gracious as always, she wished me luck and I reciprocated.

Date #40: Tanya the BFWBF

Best Friend with Benefits Forever. Tanya is a cute chick, single mom of an independent teenager, my age, with a sexy chubby body. Hips, ass, a little belly and adorable A cups. And despite being in her early 40's, she easily looked 10 years younger. On the app she looked ok, but in person she was much prettier I couldn't stop staring at those tiny handfuls peeking under her loose sun dress.

We immediately had a great vibe and banter going and she was "figuring out what she wanted" which seemed perfect for me. We had a nice, low-key dinner, making fun of the waitress whose ass was hanging out of her shorts, despite constantly readjusting them. From there, we made our way to a brewery for a night cap and at the end, I kissed her.

"It's about fucking time."

"Oh, I'm sorry, am I supposed to just slap the fork out of your hand and make out with you at dinner?"

"Ok, fair point."

"I mean I could have."

"You probably could have."

"I know it."

"So cocky!"

That's how it is with Tanya. We are constant banter, wise-ass comments, teasing and making fun of each other. She dug deep into my past in the days following our date and all but told me she didn't see anything serious in our future. While I really like her, she's not my ideal as far as looks are concerned, so I was comfortable with it.

'When are we hanging out again?'

Our usually good morning greetings paused with a more serious inquiry.

'I don't have plans tonight and don't want to be presumptuous, but maybe come over?'

'Be presumptuous.'

'Ok, come over tonight.'

'Where do you live again?'

She made fun of me for living so far away and the date was set. Well, not a date as she likes to remind me every time she comes over, but the evening, and our entire future, was set.

Tanya showed up about 30 minutes later than we planned and proceeded to pull several beers from her tiny backpack. She had specific tastes and my Miller Lite was not on the menu. As directed, she was wearing "comfy clothes" a loose flowing cotton dress that a mere breeze might lift off her body.

Plopping down on the couch, we scrolled through the streaming apps and happened upon one of my favorite movies, one she hadn't seen before. I sipped some wine and she drank her beer while we got comfortable, her draping her legs over mine and the bottom of her dress sliding up her thick milky thighs.

I rested my hand on her leg, gently caressing towards her inner thigh, inching my way up as I teased. She scooted down, spreading her legs open without a word, or even a look, inviting me in deeper. I played between her thick thighs, lightly brushing her black lacey panties and feeling her warmth. She began gyrating slightly with each graze until I felt her essence seeping through the thin sheer lace.

My member throbbed as I began rubbing her plush, dripping mound. Sneaking a finger under her panties, feeling her freshly shaven pussy practically gush over my fingertips. Swirling my middle finger around the opening she slid down further into me, spreading wide and tossing her head back over the arm of the couch.

Probing deeper, I rolled to my side into her, switching hands and two fingers inside, massaging her G-spot and lightly thumbing her clit. Her pussy was fat and sopping wet, begging me to give her more. Standing up, I reached my glistening hand out for hers, pulling her up and dragging her to my bedroom.

I lead her in, pushing her in front and shoving her over the bed.

"Candles?" she quizzed, looking back over her shoulder as I lifted the dress over her wide ass.

"Of course."

"Are you trying to be romantic?"

"Nope, just making sure the place smelled nice."

She squealed as I slapped hard on her bright white cheeks, sending ripples throughout her flowing flesh. Dropping my athletic shorts and stroking my cock, I pulled down her thong and tapped her thighs to spread her open. I reached under and rubbed her pussy again, her inner thighs wet with her excitement. She turned to her side.

"When's the last time you had sex?"

"Not too long ago."

"Have you been tested?"

"I have, but I also use condoms."

"It's been a long time for me, but I've been tested as well."

"Are you telling me to just go in?"

"I can't have any more babies, so I'm willing to trust you if you don't want to use a condom."

"Roll over."

She laid onto her back, scootching up the bed and spreading her legs wide. I tore my shirt off and climbed on top of her, running my hands up under her dress and shoving it up to her chest. She wriggled and squirmed peeling it off and tossing it to the side.

My fat cock strained against her chubby labia. As I mounted her, I rubbed it up and down while we kissed deeply. Her steamy pussy engulfed me and the divining rod found its way in. Thinking back to Tracey's nervous vice of a canal, I eased myself at first, but Tanya was completely relaxed, soaking hot and ready for as much as I could give her. Very quickly my paced jumped and the smell of sex permeated the air with my fervent pounding. She bit my lip and breathed heavily into my mouth as I slapped myself against her, the slickness of her womanhood almost splashing as it dripped between us.

She held my flexing arms as I rose above her, drilling her depths like a thousand deep ocean oil rigs. Cute little moans and hums broke through her lip, firmly clamped in her teeth. "Oh fuck, Jack! Fuck me from behind!"

My meat slapped my stomach as it plopped out and I sat back, her ample juices dripped from my balls and a notable spot bigger than my hand remained on the comforter. She got on all fours, reached between her legs and rubbed around her gaping pussy while I shifted forward and slid myself in.

Gripping her voluptuous hips, I felt her nails graze me as she rubbed her clit and I pounded away. A bead of sweat rolled off my nose as she screamed, "HARDER, I'M CUMMING!!!" Clamping down on her hips I crashed into her to the point where it almost hurt my pubis driving waves up her plump ass.

"OH! OH! OH! OH! OOOOHHHHHH!!!"

A tsunami of hot fluid sprayed my sack and ran down my thighs as she clasped the bedspread and pushed back into my thrusts, her body trembling like she was drowning in an icy river. I was unrelenting as she fell forward and onto her side in an attempt to recover her sensitive loins, but I followed her, immediately straddling her legs and shoving my cock back inside.

"OH GOD!"

Pushing down on the back of her neck and grabbing a fist full of her hair, I continued railing her into the cool puddle of her ejaculation. Wet slapping noises echoed as I reached orgasm, filling her to the brim with my cum. A few more pounds and a soft rhythmic grind took over when I laid on top of her and bit on her shoulder. Forcing me out into our pool, she swirled her ass into me, as I rolled off.

Laying there in a heap of exhaustion, I lamented her squirting.

"Do you squirt all the time?"

"Only when I cum real hard."

"So, I did a good job then," I laughed.

"I don't want to say yes because you're already too cocky."

"I think you just did."

"Honestly, I haven't cum like that in forever."

"High five?"

"Get the fuck out of here" she panned.

"No, you get the fuck outta here, I have laundry to do apparently."

"I'm sorry."

"Don't be, it's a compliment."

"It is. I know you guys love that shit."

"I... actually don't."

"Oh my god."

"Don't be embarrassed, it's fine. I have a mattress cover for a reason."

"Exactly what every girl wants to hear."

"As if we aren't being honest? Don't go catching feels."

"I definitely will not."

"I've heard that before."

"Are we being honest?"

"Always."

"Well... honestly... I think you're kind of broken."

What ensued as we stripped the bed and took a shower ended up being a really productive conversation about just what in the fuck I was doing with my life. I was really open with her, telling her all of the gory details of my love life, past and present.

Within that conversation she acknowledged she had a psych degree and worked for a bit as a counsellor before switching careers. With a deftness, she was able to crack my hard exterior and help me understand a lot of things about myself, some of which I didn't want to admit. Kind of like Maura, but without the manipulation of trying to break me down for her own benefit.

I knew I was addicted to dating and her views really helped me wrap my head around some things. As an ongoing friend, who loves "to be folded up like a taco and fucked to death," she's a great asset to my mental health. My therapist loves her for me, though isn't quite sure about our "relationship."

We talk about everything. No holds barred. I tell her about all my dates. She confides about her struggles with her teenage son. I always fuck with her about our VAST political differences and she lovingly refers to me as "fuckboy Jack." She also told me I was on a social media site that women use to vet their dates to make sure they're safe, honest, and not married. I think that whole thing is a little sketchy, but I have glowing "reviews" from various women I've dated, so I can only view it as a positive for me at this point.

I value Tanya's friendship a lot. Easily the healthiest friend with benefits relationship I've ever had. We talk every day, she checks in on my sex and testing status, along with my mental health, and I'm always double-checking to make sure she doesn't have feelings for me. Best girlfriend I've ever had, despite there being zero chance for either of us to want to make that move.

It's wild. I've never found it easier to communicate with a woman so intimately. Zero regard for hurt feelings, no need to keep any thoughts to ourselves... just pure uninhibited, honest communication. And the couple of times I've gotten into a relationship, she's always quick to give me distance and wish me luck. Genuinely, wishing me luck. It's really great.

I just know whenever she comes over, it's going to be laundry day so I went ahead and bought a 2^nd comforter and bed protector so I'm not up in the wee hours every night waiting for the dryer to finish.