Life Begins at 50

I bet she's soaking wet, I thought. I slid onto the bed and inched my way to her, sliding my hands under her legs on either side of my head. Inches away from her pussy at this point, I took a deep breath and started licking her. I could see how moist she was, and her skin parted easily allowing my tongue to wander up to her clit. Her body froze and she let out a meek "Uuuuhhhhh" while placing her left hand on the top of my head. I had no idea where her right hand was - probably playing with her nipples - because I literally could not see it over her belly and breasts, which were gently heaving at this point. Given her size I knew I needed to get my fingers involved to really make her cum, which aroused me even more. Can't wait to slide inside her and make this bitch scream while I pound away I though. It was less of a thought, actually, and more of an instinctual, reflexive, dominance. Almost like a challenge, I had to dominate her simply because of the size difference. It's my fucking CONQUEST, I screamed inside my head.

"Stick that cock in me now, and fuck me like an animal you silver stud!", she screamed with her head back against the pillows. Her legs were shaking a bit and I had guessed that it had been quite some time for her, as well as me, since she last got laid. I wanted this to be good for us both, as we had genuinely been enjoying each other so far. I pulled my fingers out, sucked and licked her wetness off of them so she could see me it. I reared up on my knees positioned my body between her legs and guided my fully erect and raging cock to her soaked pussy. I placed the head up against her, and stared into her eyes and I slid all the way in. "OH MY FUCKING GOD BABY!!!" she moaned, staring into my eyes. She violently shook and grabbed my ass, and I grabbed both breasts "You horny bitch - take my cock!" I growled. Her eyes widened and I started sliding in and out with long, slow, deliberate, and forceful thrusts. With each thrust forward her body shook - belly, breasts, and all. She closed her eyes slightly and started talking complete gibberish. I still have no clue what she was trying to say, and like then, I still don't care. It was so damn erotic to have aroused her so much that she had started cumming uncontrollably. Again, her athletic prowess surprised me, and she was clearly in better shape than I anticipated at first sight. Sexually she was a goddamn beast - her orgasm lasted several minutes, and by the time she was finished, we were both sweat-soaked and exhausted. At some point I pulled out and exploded all over her, and then collapsed on top of her, my head resting between her massive breasts. She left one hand on my ass and the other she placed on my head, cradling me and holding me in place while we both recovered from a surprisingly exceptional sexual experience.

At some point, we ended up on pillows next to each other, with her head resting next to mine. We were engaged in some playful banter and small talk, thoroughly enjoying it and realizing, surprisingly, that we both had a fantastic time despite the obvious differences that might normally keep two people like us separated. Despite all of that, as had happened with the others I met, we parted ways pleasantly but never saw each other again.

I checked my phone after recounting that escapade and realized I missed a text message from Sandra, saying she hit some traffic and was running about 15 minutes late. Time for a few more trips down memory lane, I pondered. However, the next memory was more of a "hall of shame" moment for me, as my mind wandered to the next girl I met - this time at her place after she finished a shift at the hospital.

Chapter 5. Hall of Shame

Some memories are better than others, and some - well - are best remembered as learning experiences. I'm not sure why my mind wandered to this particular tryst - perhaps I just needed a dose of humility. Live and learn I thought, And damn, I've learned a lot recently.

In retrospect, with this humiliating experience I was able to realize that I wasn't the hot fucking stud that I wanted to believe I was. Perhaps it was my age, perhaps it was the desperation of my circumstance simply looking for some form of enjoyment to replace the lack of anything fulfilling with Ann. Reality has a way of hitting like a truck when least expected.

It began playfully, with the standard type of hook-up app back-and-forth banter I knew well. Things moved so quickly that by the time we were about 15 minutes into texting she had given me her address and I was on my way. A quick trip north on the 405 to the valley and then a short distance on the 101 to her apartment, and before I knew it we were in her bed.

She was young, black, and fit, and I was in good-enough shape to keep up, but she wasn't interested in the normal foreplay "Baby, just get hard and fuck me." She had a very plain studio apartment, dimly lit with a warm yellow light coming from a corner floor lamp. My cock was hard enough, but there was this nagging sense of Why the hell are you here in this dump of an apartment? At that point, I guess I just wasn't up to the task at hand.

Putting on the condom also helped to kill the mood for me. I had come to realize since then that I really had to have some kind of emotional connection - the stronger the connection the better the encounter would be. ALWAYS. She just wanted to fuck and cum and get on with her day. Despite the desire I thought I had to do the same, nothing was working the way I wanted.

I couldn't get hard enough, and when I did and was able to slide inside her she started bucking like an animal in heat. In any other situation this would have been great. However, she was not interested in any kind of kissing or having her young perky brown nipples sucked. Before I knew it I had actually come to close to orgasm blurted out "Slow down baby!" but it was just too fucking late. I blew my load inside of three minutes and got soft again. I could feel the disappointment and frustration emanating from her, but said "I can go another round, just give me a few minutes."

I remember trying everything I could to get hard again, but another condom and no foreplay was not going to make this work. She looked at me with hard cold eyes and simply stated "Ok. We're done. It's time for you to leave."

I briefly opened my mouth to say something, but nothing came to mind. I glanced down at the bed, not even looking at her body, and certainly not her face. I damn sure don't need to look into those condescending eyes I remember thinking quickly. I dressed quickly, apologized for not being able to make it work as I had expected, and walked out the door while I tucked my shirt into my pants. Or was it my tail tucked between my legs? I thought.

On the drive back to the house, I figured I should go online and get some pharmaceutical assistance for the next encounter, after nursing my injured pride back to health.

Chapter 6. The Hot-Crazy Matrix

I opened my eyes, realizing they had been closed for quite some time now, recounting the good, the bad, and the ugly I had dealt with over the past two years. Feels like that is all over though, now I thought. Those calming thoughts came up from time to time. Seriously - how the hell did Sandra and I manage to find each other in this rat's nest of crazy we call Los Angeles? I really didn't care that much at this point - she would be here soon and I just could not wait much longer for her office visit.

As I continued to consider the chances of Sandra and I meeting when we did and how we did, I also suddenly realized that there was one more woman that helped me get over Ann these past few years...even though we never met "IRL".

Brittney and I connected on the same hook-up app I had been using and successfully dodging the prostitutes and scammers. Their game was easy to spot almost immediately. They all used the same terms, had the same conversational texting style, and always hit with the money grab. After hooking up with these various women I never needed to pay for pussy - at least I was lucky that way. Some poor dumb bastards have to pay for it all the time I thought while I smirked.

Seemed ironic to catch myself in a moment of arrogance after recounting one of the absolute worst sexual experiences of my life.

My first thoughts went to Brittney's profile - she preferred older married men and had a profile pic to boil even the coldest blood. I felt instantly drawn to her then, and reached out texting "I'm exactly what you are looking for." Amazingly enough, I got an almost instant "How's that??" response. That snarky playfulness always underlied everything Brittney said or texted, even though sometime the shit she said was borderline racist - even though she was pointing out some things that I had noticed about the same people she was deriding. I remembered during one of our discussions that she said one of the things she really appreciated about me was the lack of criticism and derogatory comments when she would just say the random edgy shit she loved to say. I was silent, you crazy bitch, because I was so gobsmacked by what you said that I couldn't respond! I remembered thinking all too often. But, given her age, physique, and looks, I gave her way more leway than I probably should have. It's called "Pretty Privilege, remember? I thought aimlessly. Weeks later I learned that she called herself a "mutt" - part Portuguese, part Italian, and part Native American - simply because of the random mix of her ancestry. Maybe that contributed to her exotic look? I wondered.

The next message I got, after we exchanged private "burner" numbers, was a short self-shot video of her naked on her bed, legs spread and sitting on her knees, gently bouncing up and down as though she was riding my cock. I sent the requisite dick pics, which she said she loved, and that we should meet up immediately. I probably should have just gotten in my car right then and driven an hour to her to spend the night, but for some dumb reason I was waiting for a phone call from another friend. Of course, as my luck would have it, that call never came. Brittney actually gave me her address and so I just thought What the fuck? What've I got to lose at this point? There's no traffic at this time of night. As good as it seemed at the time, when I arrived at her apartment complex and finally got through to her on text, she was a bit shaken that I was there. Took her a bit too much by surprise I thought disappointingly. My fucking god that would have been off the charts if I played my cards better!

Over the next year Brittney and I continued to use the burner text numbers to chat, until we realized that we needed to have our "real" numbers to keep in touch. At that point it started to seem more serious, but there was always those nagging thoughts of Is she real? How crazy is this one? Assuming she was who she said she was, the virtual relationship was progressing rather nicely, and we had even planned to spend our first night together in a local hotel...and somehow it was also the EXACT same night that California shut down completely because of the COVID-19 pandemic. Curfew was put into effect, and only necessary travel was allowed. Terrific! The last damn thing I need is to have to explain to Ann da fuck I'm doing at the LA police station at this time of night! I remember thinking angrily as Brittney and I cancelled the plans we had been working on for so long.

FaceTime mutual masturbation sessions with Brittney were electrifying and erotic as all hell, but her edgy and at times condescending manner really bit a little too deep. That was part of what I hated about Ann I remember realizing, all too late in the game with Brittney. There was no way I could really have anything long-lasting, serious, or deeply engaging with her. I may have realized that earlier than I admitted, because in our conversations I ended up pushing her away. Despite all the playful conversations, sometimes lasting over an hour, the erotic and explicit photos we sent each other, the videos, and the mutual masturbation orgasms we shared, this one too eventually waned out of my life. Was she real and as crazy as I now realized, or just another catfish?

Chapter 7. Another Broken Soul

My phone buzzed with another received text message from Sandra - she had approximately 20 minutes left before arriving, and my thoughts drifted again...

"I pick you...now how does this work?" read the text message.

That was the response to the text message asking about meeting up and enjoying each other's company, after a few initial playful texting sessions. Nothing too explicit, though. Not yet...We had been considering getting coffee first just to meet in a safe space and see if we really wanted to go to a roadside hotel together for a few hours.

I remember smiling - that same half smile with the right side of my face when I knew I was going to have a fan-fucking-tastic time, at least for a little while. Keilani seemed interesting enough - and had the sex drive I'd been looking for. Too bad she turned out to be just another broken soul, hurt by the kind of toxic, insecure, neanderthal male that made the world a bad place for all men. Had I known that at the time we started seeing each other, I could have saved myself a year and not endured the insane jealousy she ended up spewing at me.

But that didn't happen until close to the end, and we had almost a year's worth of sneaking around, fucking like teenagers, and even spending a day together in a hotel. At that point it really felt like it could have gone somewhere nice. Boy am I glad it didn't, I thought with a sigh of relief. I never would have been open to seeing Sandra, and that would have been the greatest loss I realized. But my mind wandered back to the first long-lasting physical relationship I'd had since Ann and I got married.

That first encounter in the hotel was electrifying, as were so many of the encounters we engaged in over the year that followed. I closed my eyes, leaned back in the chair again, and remembered walking up the wooden staircase from the parking lot. I was always cautious, almost to a point of being silly about it, to avoid being caught on camera. Many times I would look around, wearing sunglasses and a baseball cap to shield my face. The first few times this certain made me feel a lot better about myself, even though it was doubtful that it actually helped. After all, I was driving the same car with the same license plates. If I was being tracked, I would have been easy to find, relatively speaking.

I walked up to the room number she texted me, knocked on the door, and cautiously entered when it was opened from behind. I saw her had on the door and her clothes on the floor, and my cock started to stir.

"Come in, baby..." she cooed.

I stepped into the room, looked to my right, and she peeked out from behind the door, in her bra and panties. I turned, and slowly closed the door with my right hand while my left placed my backpack down on the desk chair. She stood there with her chin angled down slightly, looking up at me with a combination of raging desire and nervous anticipation on her face. I stepped back from the door, towards the bed, and beckoned her to come to me with my right hand. She obliged, and took three quick steps over to me. We embraced immediately and our lips locked together, tongues dancing around and our breath quickened. She pushed her hips against me, and my cock, now fully engorged and straining against my clothes, pushed back begging to be set free.

I remember deftly unhooking her bra with my right hand - I got really good at doing this - something I had failed at epically when I was younger. Practice really does make perfect, I thought. Unhooking the back and pulling off the bra set her breasts free - her nipples were hard and the size of pencil erasers. Just as pink as well, I exclaimed to myself. I pulled my lips away from hers, cupped her right breast, and bent over to take her nipple in my mount. I was taller by at least 4 inches, which was new to me, and it excited me even more. Perhaps it was the perception of being that much easier to dominate her completely. Doesn't fucking matter - get her in the bed and ravage this sexy bitch! I thought. Although she was definitely older than the other women I had met, she was fit and lean for her age - a well-kept physique was a site for sore eyes. Ann had really let herself go the past few years, and even though I never really "saw" the added weight on her, I certain saw what I was missing now.

As soon as I had her nipple in my mouth she tossed her head back and moaned, grabbing the back of my head and thrusting her hips against my cock again. "Yes baby! Oh my fucking god I missed this!" she moaned loudly. I reached over to the dresser top and quickly turned on the TV with the remote that way lying there in the dim light. Only the overhead light from the adjacent bathroom was on - probably in an attempt to set the ambience and make this more romantic - and it worked. I just needed a little volume from a source other than us, to try and make our heated encounter less obvious to any neighbors. I doubt this will work but it's worth trying, I hoped.

I continued to work on her nipples, alternating between them. I sat down on the bed with my legs spread slightly, and she started unbuttoning my shirt. I came directly from the office and was dressed accordingly. I left early to avoid as much traffic as possible on the LA freeways. They were always a clusterfuck, and I had to keep a reasonable schedule so as to not arouse any suspicion at home. At that point I was still living with Ann and needed to keep it that way.

I ran my hands down her body and slipped them under her g-string. She had my shirt completely unbuttoned and had pulled it down past my shoulders. I stared into her brown eyes briefly before kneeling and pulling her panties down to her ankles. Doing so revealed a perfectly shaved mons and softly defined pussy. A gentle swell above her clit and around her lips begged for my tongue, but before doing that I had to get the rest of my clothes off. I teased her a bit my kissing and sucking on her clit for a moment - and she let out an audible GASP, as her body froze in front of me. I looked up and her and growled "Get on the bed, now!" She put both hands on the top of my head and paused a second or two before nodding with her eyes wide open, giddy with anticipation.

She slid to my right, turned around and sat on the bed. She leaned back with her ass on the edge of the mattress and spread her legs, enticing me to continue. I stood up, removed my shirt, stepped out of my shoes, and slowly unbuckled and removed my belt. I let it fall to the ground and the brass buckle made a soft click as it hit the carpeted floor. I undid my pants, all the time staring into her eyes while she played with her clit and ran her fingers up and down the entrance to her pussy, which was clearly wet and ready for me.

My cock sprang forth once freed, but I had other ideas in mind before we "got to know each other". I knelt down once more and slid my arms under each leg, hoisting them over my shoulders. I remember bending forward and pulling her lips gently aside just in time push my nose against the hood of her clit and nudge it upwards. I slid my tongue out of my mouth, teasing her clit and then wrapped my lips around it and starting lapping at it like I was a cat with a bowl of milk.