Life Begins at 50

Pants dropped to my ankles and she pulled my bicycle-shorts style underwear down and got on her knees. "Sit down baby. I want to swallow it all." The texture of the chair felt a bit rough against my skin, which I soon forgot about once she took the head of my erect penis into her mouth. No teeth again, I thought and smiled. She aimed to please and I was not disappointed.

My hands were resting on the armrests and my back was up against the chair. I spread my legs and slid down into the chair a few inches as she took my entire length into her mouth. I still hadn't had penetrative sex with another woman - but the feeling of her warm smooth mouth and soft tongue was wonderful. She was bobbing her head up and down in my lap, with the associated "Gah...Gah...Gah" sometimes heard in porn. I pushed her hair to the side. It had fallen down covering her face and I wanted to watch her. Watching was just as erotic as the sensations she was artfully creating. Her soft red lips formed a perfect seal against my skin and her hand wrapped around the base of my shaft rotated back and forth, almost in a rocking fashion. The mix of her floral perfume and a hint of sweat was intoxicating. My hands gripped the armrests, and my fingers sank into the cushioned frame. I arched my back slightly and slipped farther down into the chair. She slipped backwards slightly to adjust and kept at it.

She'd suck my soul out through my cock if I let her, I remember thinking. Surprisingly we had only been at it for a few minutes but somehow she had me almost at the brink. Her skills were damn near perfect, and I was only moments away from cuming in her mouth. I remember telling her to slow down, that I was getting close, but she looked up and me, gave me a devilish grin, and went at it that much harder - like she had been waiting for this moment. She knew without a doubt she was in control, and she also knew what she wanted. There was absolutely no way a weak attempt on my part to ward her off and slowdown was actually going to work.

She took a deep breath and thrust her face into me, jamming my cock all the way in and I could feel the pop of my head passing into her throat. I remember losing control and grabbing the back of her head. I thrust my hips up but her hands managed to slip past me on both sides, grabbing the back of the seat cushion, and she held me down. I exploded inside her mouth, and just like the woman in Kansas City, she swallowed every time my cock contracted and pumped a load of semen into her. My legs were shaking and my ass was contracting and she just held me there and drank it all. As the contractions slowed and the squirting stopped, she swallowed the last of it, and took a deep breath in through her nose. Still face down in my crotch, she turned her head up to me and met my gaze. I could see the desire and hunger in her eyes, and the satisfaction of a job well done.

She released me and I began to slowly soften. I reached for a tissue on the glass toped side table between the two chairs so I could dry off. Her saliva soaked my cock and my balls, and I didn't want to leave a wet spot on the chair. She sat back onto her knees, and I handed her a clean tissue. She proceeded to clean her face and jokingly mentioned that she didn't want to just walk out looking like she had drooled all over herself...even though that's exactly what she looked like. I got dressed and turned the music volume down a bit. No need to have that blasting into the hallway - it is a workday for fuck's sake I remember thinking. After some small talk about how wonderful that was, how much she loved how I tasted, that we needed to meet again, and see what else might happen, I walked her to the elevator and remember the coy grin on her face as the elevator doors closed. At least we got together a second time I thought.

A text from Sandra grabbed my attention again, and I smiled. Only 45 minutes away, I thought as I dove back into my memories.

The next time Maya and I got together was better. Similar small talk while we walked from the elevator to my office, however this time one of the other tenants on the floor passed us going the opposite direction. He looked at her and gave me a knowing smile, which she missed, thank God.

After the office door closed with a soft click, she turned around and opened her mouth, about to say something. "Is there anything I can do for you this time?" I asked playfully after the door was closed and locked.

"We will see about that. I was so wet last time - I had to use my toys when I got home and, well, that was good enough...but your cock gets so hard and it would feel so much better than my dildo" she said nervously. Unexpected honesty from a complete stranger is still refreshing, I remember thinking

I walked over to Maya to undress her, but she put her hand up and said "Sit down first, baby. I want to taste you again."

I started that familiar backwards walk to the same chair. "As you wish" I said in a deep and raspy voice. She quickly caught up to me and put both hands on my chest, and playfully pushed me down into the chair. I unbuckled my belt, which was barely audible over the music. She deftly pulled off my black Johnston & Murphy loafers - which felt like slippers now from wearing them so frequently. She slid her hands up my legs, and I could feel the hair standing on end as her hands passed up closer to my cock, once again straining to be released. She locked her gaze to mine and expertly unbuttoned and unzipped my pants "Lift up baby" she said softly in my ear. I pressed my hands down onto the arm rests and lifted myself off the chair, closer to her face, and she smiled. My pants were down around my ankles faster than I thought possible, and she then did the same to my underwear. As she did, my cock sprang out and in one smooth motion, took me in her mouth while taking both my pants and underwear off my left leg.

I let out a satisfied moan and sank into the chair, releasing my hands from the armrest and moving my dress shirt up and out of the way. I enjoyed watching her perform her art.

She pushed herself down onto me and took my entire length into her mouth. Like watching her eat her favorite dessert I remembered thinking. Maya was certainly treating me like that - with the perfect balance of ravenous desire and softness. I slid easily into her warm smooth mouth without any resistance. The texture of her tongue gave just enough friction on the head of my cock to keep pushing me closer to orgasm, without being too rough, as she slowly bobbed her head up and down. I let out another low moan, or perhaps it was a growl, I can't remember. Her scent was intoxicating, again. A mixture of floral perfume, with a hit of lavender, and her sweat. Those clothes need to come off I thought, letting my mind wander again.

She continued to suck and lick, using her soft hands to massage my balls and the base of my shaft, but I wanted to last longer this time. Very often if I could stop the stimulation right before climaxing, just before the hot rush of muscle contractions began, I could hold off for a long time. If the timing was off by a fraction of a second, I would release. I remembered back in my thirties when I was an exercise fiend I could hold myself there - right at the brink - and release almost on command. That made for some amazing simultaneous orgasms with Ann when we were still crazy about each other. Even now those memories made me smile - those were good times and there was no reason to discount them just because we failed. Everything that has a beginning has an end, I thought.

I was getting close but she was not slowing down or relenting, and I remember feeling it - missing the timing even though I said "Stop - I'm close!"

But it was too late, and even though she released me from her mouth and sat back on her legs folded beneath her, I could not stop. My balls pulled up close to my body and the muscles at the base of my cock were contracting at the same time. I started pumping semen out onto my abdomen, as some of it also rolled down the head and dripped off. Towards the end of my orgasm, it had dribbled down my shaft as well. We locked eyes. I smiled and looked at the mess I just made and then back at her, beckoning her to come clean me up.

Her eyes widened when she realized what I was suggesting, and she licked her bottom lip while focusing her gaze at my softening cock. She scooted on the floor close to me, spread my knees apart, and started cleaning me off. Licking, sucking, and kissing it all into her mouth. Swallowing while moaning - not because she enjoyed the taste - I assume she did - but because her left hand was nowhere to be seen. I watched her gyrating and then realized she was masturbating while eating the warm creamy present I left for her.

I had no idea that during her ministrations she had removed everything from her waist down. Now the thought of us both being naked like that refocused my attention to what was obviously next - and we had both hinted at it during her previous visit.

We talked a bit about what just happened and I apologized for losing control to which she replied "It was perfect. I made you lose control and that is so fucking EROTIC...don't you dare apologize, baby."

"Looks like you really enjoyed it too - all of it. And watching you right now is turning me on again, Maya"

I could feel it before it started to show - the muscles tightening and the blood flow increasing. My cock was slowing coming back to life while I was slumped into the chair. My ass was hanging off of it and my back was almost flat against the seat cushion. I picked myself up a bit to relieve the strain on my neck, as my pulse was quickening. Maya glanced at my cock which was erect and now twitching in perfect sync with my elevated heartbeat. Watching her play with her clit while she sat there was the perfect stimulant. It was that jolt of caffeine in the morning after first waking up.

"Keep your left hand where it is the entire time - let's go for round two. I want to feel you swallow each time I pump a load into your mouth. I fucking LOVE that." I stated.

"I wouldn't have it any other way, baby" she purred. Before I realized it her head was in my lap, right arm resting on my left leg, hand holding the base of my cock, while she gently licked and kissed the head. I could smell the sweet mix of perfume and sex, again, and it made me even more ravenous. She kept at this for quite some time. Every now and then I could hear her moan gently and feel her body tense while she continued to bob her head up and down. She's really getting into this, I thought, as I placed my hands on the back of her head. "I think you can make me cum three times today Maya...and the third time shouldn't be in your mouth."

She paused with me buried in her mouth and looked up into my eyes and smiled. I felt her tongue dance around my shaft with my head pressed against the soft palate of her mouth, and she started pulsing her throat. I'd never felt anything like that before, and this devilishly kinky bitch was just waiting for the exact moment to spring this on me. She closed her eyes as I pressed both hands down onto her head, burying her nose into me, and feeling the silky texture of her hair. I still don't know how she did it, but within a few short moments I had arched my back and exploded into her mouth without any possibility of control. She literally sucked my load right out of me...with every convulsion of my body and pulse of my cock she swallowed and moaned. It was the best blowjob of my life.

I whimpered and slouched back into the comfort of the chair. "Oh my fucking GOD! What the fuck did you just do to me?" I couldn't feel the texture of the cloth against my skin anymore as I was still reeling, dumbstruck, by what just happened.

"Baby, I told you I loved sucking cock. And that little surprise at the end is something I've been trying to perfect for a long time - and we just did. I'm so fucking horny - you made my fantasy come true and I need to feel that gorgeous cock of yours explode inside my pussy. I'm throbbing for you. I'm on the pill too, so you are going to leave it in. I'm gonna ride you right there in that chair as soon as you are ready. How about you keep watching me play with myself first? Then I'm going to come over there, straddle that chair, and slide down onto you."

She stood up and looked at me like I was the prey and she was the predator, which was not a position I was accustomed to being in, but I really didn't care. It was erotic and powerful and passionate. Just what I needed, I remember thinking. She slowly removed her blouse which revealed ample breasts almost bursting out of a bra that was just a bit too small. Looking at her, naked from the waist down and nothing but her bra on top, masturbating while standing directly in front of me did the trick, and my cock was springing back to life. She stopped rubbing herself momentarily, licked her pointer and index finger, and then reengaged with her clit. "I'm soaking wet baby. You are going to slide right in and I'm going to slide down on your thick and veiny cock. I'm going to bury you inside me and grind on you like a bitch in heat, you fucking stud" she growled.

She took one step towards me and I leaned forward to accept her...

And then came the worst timed KNOCK on the door in the HISTORY of door knocks.

BOOM BOOM BOOM.

The door shook and she squealed, grabbed her clothes, and ran into one of the offices adjacent to the reception room. "Be right there" I croaked, with my head pointing away from the door, in a pathetic attempt to sound like I was farther away.

I dressed quickly without cleaning up - just her saliva again - she got every last drop. I answered the door and signed for the damn FedEx package. I hoped the awkward bulge in my pants wasn't noticeable, but then again, there was nothing I could really do about it.

I turned around as the door closed softly to see her peering out from the office she ran into. She stepped out fully clothed. How the fuck did she dress so quickly? I wondered. We both looked at each other and burst out laughing, even though we were clearly disappointed that we were interrupted. "It will have to wait until next time baby" she said as she looked at her watch. "Traffic is going to suck right now."

We bantered the same small talk walking back to the elevator and said our goodbyes somewhat awkwardly, both a little confused and frustrated, but still horny as could be.

A few days later I received a text that stated bluntly "This isn't working for me." I never heard from her again.

Chapter 4. Finger Lickin' Good

At this point I was getting restless for her. Reliving my past trysts had my cock straining against my pants and my desire for Sandra close to an all-time high. I hope she's as lustful as I am right now I wondered. Do I tell her about what just happened with Ann before or after? I considered the outcome of both, and realized it didn't matter - we'd be just as happy either way. Then again, I thought, telling her before could really ignite her desire, as it was doing for me.

The next affair, I realized, was one I had never considered having - not that I ever really considered having ANY affairs, but this one was different. I had never been with a bigger woman and didn't really find them to be my type, but you never really know what you might enjoy until you give it a try. I'll try almost anything once, I remembered thinking when Daisy and I were texting. I had returned from another trip to Kansas City during the pandemic, and vaccines were still "not a thing" yet. Ann demanded I self-quarantine for two weeks as per the CDC guidelines, and after my first quarantine, I was definitely not going to argue. As was the case for me those days, my libido was more in charge of my bad decisions that I was, akin to my teenage days.

My phone buzzed - a new text message from Daisy saying she arrived. I sent her my hotel room number and invited her up. She knocked shortly thereafter, and I ambled over to the door, nervously anticipating what was going to happen next. From our playful banter back and forth on the hook-up app we were using, I knew she wasn't an average sized woman - but I did not expect her to be as tall as she was.

I opened the door and immediately though DAMN - she IS a big woman - no turning back now though. She smiled and said "Hi baby." I gave her a knowing glance, invited her in, and closed the door. She walked over to the bed in the dimly lit room and it was then that I noticed she really had dressed the part for a one-night stand: a short black leather skirt, purple lace top which stood out against her dark chocolate skin, and thigh-high boots. As large as she was, she made the outfit for her body - which actually excited me - surprisingly. I felt the familiar stirring in my cock and balls and forgot about my earlier misgivings about how this was going to go.

"Time to get you out of all that" I purred.

"Mmmmmmm hmmmmm" she cooed in response.

Her jacket fell to the floor and revealed the largest breasts I ever had the chance of getting to know better, and my eyes widened with anticipation. I ran my hands up her arms to the top of her shoulders, which were several inches above my own. I slipped the straps of her top down around her shoulders and slid around behind her to undo the bra hooks.

Sliding Daisy's bra straps down her arms and undoing the hooks let her ample breasts free, which I immediately focused on. As soon as I wrapped my lips around her dark brown nipple, she let out a soft moan and reached around to grab the back of my head with both hands. She gently pushed my face into her breast. "Oh baby" she cooed, "that feels wonderful..." I looked up at her, looking down at me, and realized she was easily six inches taller than me. I forgot we were still both half-clothed and standing next to the bed. My cock was growing as I sucked and licked both nipples, alternating between them when I felt one had enough attention.

We maneuvered our way to the foot of the bed, shedding clothes as quickly as possible. As soon as she pulled my underwear off my cock sprang to attention. At that point she was lying on the bed, while I was standing next to it facing her. Her dark chocolate brown body was faintly illuminated by the single nightstand lamp I left on, and I thought again Damn that's a lotta woman. She expertly engulfed the head of my cock and toyed with my balls with her long fingernails. It was my turn to moan, in appreciation of her talented lips and tongue. She grabbed my ass with her left hand and pulled my closer, pushing my fully erect cock all the way into her mouth. With her eyes closed she started bobbing her head. "Fuuuuck" I moaned and I realized if it went on much longer I was going to blow my load straight down her throat.

I'm convinced that she sensed I was getting close and released my raging erection from her mouth. She gazed up and me and smiled, and before she could say anything I blurted out "My turn, baby." She smirked as if anticipating my response, turned, and rotated faster than I thought she would, resting her head on the headboard. Her large breasts rested on an ample tummy, and her legs spread to reveal my target. Being as large as she was, her vagina was not as well defined as some of the slimmer women I'd been with, but then again, my soon-to-be ex-wife wasn't a stick figure either. I had grown accustomed over the years to more of a vertical slit than well-defined labia and a visible clit. The first time I'd seen such definition in a woman's genitals I was instantly aroused - more so than ever before. I lusted after that definition, but at the same time found some level of comfort with the simple vertical slit I had been experiencing for almost two decades with Ann.