App Finally Pays Off

Well, this isn't where I expected to find myself: in my mid-40s and newly divorced. No great scandal to it; we got together very young, and as we grew older, we grew apart. We were still great friends, but there was no spark left, and we made the decision to split before resentment could spoil the friendship. After all, due to the kids, we were always going to be in one another's lives in some way.

So, I find myself single and completely at a loss as to how to be single. I have absolutely no desire to get back into a committed relationship, but my libido is through the roof.

I find myself watching so much porn that you could have easily mistaken me for someone less than half my age.

It was during one of my trips to my favorite site that I saw an ad for a hookup site, which I thought was worth a try. The idea of a mutually beneficial relationship without the risk of commitment or leading anyone on sounded like the perfect solution to my current predicament.

Having signed up, I was overwhelmed by the number of people messaging me. It was too good to be true. Literally, within a matter of minutes, 15 beautiful "women" all wanted a piece of me. It became instantly apparent that the site was a scam. I had to buy credits to reply to these messages. It was amazing how many of the women messaging me fell into the categories of blonde or brunette, whose facial features were so alike, it almost felt like AI had a hand in their creation.

Well, while it wasn't what I was hoping for, I'd realized before I had spent a penny. I felt like I'd had a lucky escape.

As the days rolled on, the notifications kept coming. I'm not going to lie; despite the fact I didn't believe it was genuine, some of the messages and images became great "wank bank" fodder. So, despite having no intention of spending a penny, I'd regularly check the messages one-handed.

This continued for a couple of weeks, and in their defense, I'm not convinced it was just porn bots. I still wasn't getting genuine vibes until Katie.

Katie's message was super underwhelming. It was a "flirt" (a small preset message that can be sent free of charge) saying she was close to my hometown. However, for all the uninspiring aspects of her message, her image couldn't have been further apart. A closer look at her profile revealed Katie was 37, married, and looking for NSA fun. It also included three images. In her first, she looked stunning. She had a real girl-next-door vibe to her: long red hair, cute freckles across her nose. The second was an image of her in a swimsuit by a pool; her body looked incredibly well-toned as she lay in the shade to protect her delectable fair skin. The third image was a picture with the head out of shot, showing a naked lady on her knees with her ankles in a spreader, and her arms appeared to be bound behind her back. If it wasn't for the freckles on the shoulders and the fair skin, it could have been a picture of anyone. Most importantly, what set these images apart from any of the others was that all three pics had a watermark in the bottom corner with an email address. It wasn't your normal, run-of-the-mill email address; it was clearly a burner email just for this purpose.

Given how hard her images had made me, I thought it was worth the risk to reach out to her. I took the precaution of creating my own burner email address and sent her a message confirming my screen name and that I had received her flirt and loved her images.

It wasn't until the next morning that I got a reply.

Katie was initially a little suspicious, as her experience on the app had been incredibly similar to mine. After a few messages back and forth, talking about some of the local bars and characters, I think we both felt confident that at the very least we were talking to a human from our hometown.

After that, it wasn't long until we exchanged numbers and moved our chat from email to WhatsApp. Bizarrely, given how we had found one another, most of the first day's chat had been clean, getting-to-know-you talk.

It wasn't until that evening when I had climbed into bed that my phone pinged again. It was another message from Katie. It was a screen grab of a message she had received on the other site. It was from a man asking if she would tongue-fuck his ass while giving him a hand job. Along with the image was the message, "Would this work for you?"

I replied completely honestly that I'd never tried it, but I would be lying to say the thought hadn't crossed my mind. As the messages continued, it became apparent that she was in a not-so-dissimilar position to mine. While she was still in a long-term relationship, her sexual experimentation had ceased some time back. We started sharing our fantasies--both long-held and some new ideas inspired by the AI app. That night alone, I came twice just fantasizing about aiding Katie with some of her fantasies and having her assist me with mine.

The following morning, I awoke with the most vigorous morning wood I'd experienced in living memory. I lazily reached for my phone and was scrolling through the previous evening's chat when I was startled by my phone buzzing, alerting me that I had an incoming video call from Katie. This was it--the moment I had toyed with so many times yesterday. I was about to get confirmation of whether this beautiful redhead was really interested in me or if this had been some poorly played-out hoax.

I held my breath as I pressed the accept button. There was a brief pause before my screen filled with confirmation that she was real. Not only was she real, but I was also greeted with a view of this delightful lady, lying topless in her bed, playing with her nipple and biting her lower lip (lip biting had been discussed as a turn-on the previous evening) before a rather sultry, "Hello." At this moment, Katie held the upper hand as she had decided to make the call and knew how she intended to present herself. I was on the back foot, taken aback by her natural beauty. It was early in the morning, and her makeup was minimal at most. But what really drew my eyes was how firm her breasts looked. I had seen images, but stills don't compare to watching how little movement there was as she teased her cute bright pink nipple.

"Hello, you," I eventually replied, as my hand instinctively wrapped around my thick hard cock. I picked up the conversation from the previous evening's chat and started describing some of the things I would like to do if I were there with her in the flesh. It wasn't long before her hand slid down her body, out of the camera frame. The look in her eyes confirmed my suspicions that she had started to tease her pussy. While I led the conversation, Katie kept adding in when she wanted to direct things one way or another. I was lazily stroking my cock as climax wasn't my goal--the stimulation overload of watching this desirable woman bring herself to climax for me, because of me, was amazing.

As Katie reached her climax, she dropped her phone, and the screen filled with a side view of her naked body. While there was nothing really on show, the sight of her smooth pale flesh as her hips started to buck was more erotic than any of the porn I had been watching. I found my hand speeding up as I heard her moan, "I need you here NOW!!" To which I replied, "Text me your address; I'm on my way." And with that, I hung up.

As I was getting dressed, I got a message with her address, accompanied by the devil emoji. I was a little shocked to find she only lived six streets away. Ten minutes later, I was standing at her door, knocking. Moments later, there she was in the flesh, standing in front of me with her body delightfully wrapped in a black silk kimono. The fabric was so thin it did nothing to hide the desirable curves that were hidden beneath. She was a little shorter than I'd expected; I'd guess around 1.65m tall. She had her auburn hair brushed behind one ear, and she looked at me with pure lust glowing in her emerald eyes.

I stepped forward, wrapped my arm behind her back, and leaned forward to kiss her. There was no building up to this kiss; it was unbridled passion. Our tongues wrestled for top position. Katie's hands ran through my hair before grabbing a handful, leaping up, and wrapping her legs around me. My hands moved instinctively to grab her luscious firm ass.

Having this gorgeous young lady, who had spent the last 24 hours working her way into my mind, in my hands with her petite body wrapped around me had blood pumping through my cock, which was now straining against my pants. I broke the kiss and lifted her over my shoulder, starting to head upstairs with my new acquaintance. I knew from our conversation last night that she longed for a man to take control of her and use her body for his own pleasure. I had every intention of fulfilling this fantasy for her.

As we got to the top of the stairs, I took a punt on which door led to the master bedroom. I guessed right; it was well-lit and well-decorated too. There was a king-size bed and a couple of pictures with Katie and who I'm guessing was her husband. He was a good-looking bloke with a better-looking physique than mine. It was instantly obvious to me that everything I was about to enjoy was entirely due to this chump's inability to satisfy his incredible wife.

As we got into the room, I let her down next to the wall between the two bedroom windows. Katie dropped to her knees as I unfastened my trousers and pulled out my overexcited, rock-hard cock. Suddenly very much aware of how the day had unfolded and watching Katie's climax, the fact I had not yet experienced my own release became my primary objective.

Pulling my eager member from my pants and watching Katie's lips eagerly take my red raw helmet into her mouth was at the time the thing I most longingly desired. The sensation of my length sliding into her mouth was almost enough to set me off. As she got about halfway down my length, Katie used her right hand to take hold of the base of my shaft. Within the blink of an eye, I slapped her hand and told Katie, "No hands." With that, I stepped forward, straddling Katie's knees/thighs. The look in Katie's eyes as she realized the back of her head was against the wall and she was at my mercy for the face-fucking she was about to receive lit up. She knew I was committed to providing her the sexual fulfillment her husband wasn't prepared to. There was no fear, no regret, just longing.

As my hips moved back and forth, my dick glided through her lips and into her throat. When it was just the first 10 cm, Katie's cheeks would hollow as she sucked on my rod, but as it got deeper, she was unable to maintain this. The sensation of her sucking and then gagging a little before sucking was like nothing I had ever experienced. As I could feel my climax building, Katie was clearly becoming more comfortable in this position. She reached up and grabbed my ass as she held me in place for just a couple of seconds longer when I was all the way in.

I couldn't hold back any longer and felt my balls tighten. Placing one hand against the wall and taking a handful of Katie's hair, I thrust my hips forward. Listening to Katie gag as I flooded her mouth with my first load of the day. My explosion was so big that even before I had finished, I could feel my sperm leaking from her mouth and dripping down my balls. Katie's eyes were slightly watering as I pulled back, but even as I pulled back, Katie sucked on me, cleaning me up before opening her mouth wide to show off my load as her prize before she swallowed it down in a single gulp.

I offered a hand to Katie and pulled her to her feet. She smiled at me as she said, "Thank you, Daddy." Now, while this had never been my kink, I was aware it was Katie's. I think knowing that actually made it feel less alien than I had expected. In fact, knowing I was taking her to places she'd been craving actually aroused me. "You're welcome, little one," was my reply, before leaning in to kiss her. As I pulled away, Katie lightly bit my lower lip and pulled on it a little as I stood up.

Looking down, I untied the belt of her kimono, then lightly brushed the shoulder off her, and it fell to the floor. Seeing her naked in the flesh for the first time visibly made my cock twitch. The freckles lightly covered most of her body, including the cleanly shaven mound above her pussy. Even from this angle, I could see her labia protruding from her sex. I looked her up and down, and Katie asked, "Do you like what you see?" to which my reply was, "Oh, little one, you look better naked than I'd imagined." "But Daddy, I'm not naked," she giggled before turning 180 degrees and looking back at me over her shoulder, where I spotted a sparkling green jewel over her asshole.

If we hadn't been so frank the previous day, I'm not sure if that would have excited me the way it did. I was fully aware Katie wanted to explore anal play but hadn't felt confident to mention it to her partner. The fact that she was so willingly offering me her virgin hole on our first play date felt so exciting. Given she was so willing to fulfill her fantasies made my head spin as to the prospect of fulfilling some of mine as well.

I strode across the room and swept her up in my arms, and I sat her on top of her dresser. I spread her legs and took a seat at her stool. From this position, she looked down on me and ran her fingers through my hair. "Which drawer?" I asked. Katie replied without any further questioning. With that, I placed my hands on her knees and started to slowly kiss up her left inner thigh.

As I approached her pussy, it was clearly wet, and her clit was swollen and visibly protruding. I briefly paused to take in the musky aroma of Katie's pussy. I then dropped my head and sucked her clit into my mouth. My teeth opened just enough so her button grazed it as I sucked it in before using my tongue to tease it. Katie responded by pressing her hips forward, eager for me to feast on her. Briefly giggling as her butt plug banged against her dresser top.

With my left hand, I started to tease her labia. Her pussy was open for me, but that didn't reduce the pleasure I got from teasing her and drawing out her pleasure. With my right hand, I reached down for the drawer that Katie had previously indicated. I knew this drawer was full of Katie's sex toys. One of her fantasies that we wouldn't be fulfilling properly today was her desire to be double penetrated. That wasn't going to stop me from teasing her with what could be if this friendship was to continue. I reached in and pulled out one of her vibrators. I placed the tip of it between my index and middle fingers of my left hand, which was holding her open, before easing the tip inside. All the while, without taking my lips away from her clit. I heard Katie gasp, "Oh yes, Daddy." As I slid the toy halfway in, I switched it on, and even I could feel it pulsating against my tongue on her clit, so there was absolutely no surprise as to Katie's reaction. She slammed her thighs shut around my ears as she pulled harder on my hair.

It doesn't take long before Katie is calling out that she is cumming, and I can feel her climaxing on my fingers. I raise my head to watch her body in full climax as I start to lightly slap her clit until she rides out her orgasm. As her breathing starts to return to normal, I stand up, looking down at Katie and enjoying the blissful look on her beautiful face. As I stand up, my cock catches on the vibrator before springing back to attention. "Oh Daddy, is that for me? Again?" Katie says while coyly sucking on one of her fingertips. To which I reply, "Oh little one, it's not for you! It's for me to continue enjoying you." I take a firm grip of her hips and pull her closer toward me.

Katie is leaning back with her head and shoulders resting against her mirror. I reach down and slide a finger either side of her butt plug before pulling it out. I don't rip it out, but I'm firmer than easing it out. I place it on the dresser next to her left hip before taking my cock in hand and guiding it to her little puckered asshole. Despite having the plug in until now, it is impressive how quickly that hole closed tightly back up. I press forward with my hip and watch the expression on her face as she receives her first helmet into her butt. She reaches out her hands towards my head, so I lean forward, and she pulls her head forward and we kiss. Our tongues dance passionately as I slowly ease my whole length in. As my pelvis pushes the plastic cock deeper into her pussy, she bites my lower lip before whispering, "Thank you."

I guide one of her hands from the back of my head to her pussy. "Little one, fuck your pussy for me while I'm going to cram my pie into your ass." Eager to obey, she grasps the base of the vibrator and starts to fuck herself at the same pace I'm pumping in and out of her ass. The sensation is unlike anything I have ever felt, feeling the incredible tightness of her ass holding me while simultaneously the fake dick internally rubbing on the top of my shaft. I pull one of her feet up onto my shoulder; this allows me access to her buttocks for me to deliver quick heated spanks. "Little one, you are my eager little slut, aren't you?"

"Yes Daddy, I'm yours! I'm all yours."

Katie starts to climax once more, taking hold of the fake cock and ripping it out of her. I then pull myself out of her. I pull Katie off the dresser, spin her around, and press down on her shoulders so she holds her weight on her hands on her dresser, presenting her ass to me from behind. Looking down, I can see that Katie isn't so fast to close this time as she is a little gaped. I quickly hammer my cock back into her ass for a couple of strokes before pulling back out and fucking her pussy. I continue to alternate between her holes as the gaping allows for a fast movement from one to another. I pull her upright and pull her arms behind her back. I slide my left arm under her arms to hold her arched back and upright as I focus on fucking her ass again. As I feel my climax building, I grab her throat and squeeze lightly with my right hand. My head closes to hers, my breath hot on the side of her face as I start to describe a scenario where we could introduce another real cock to this situation.

I feel my balls tighten up again, release her throat, and glide my hand down the front of her slender body to start teasing her clit again as I explode into her tight ass. It feels like the longest orgasm of my life, as with each thrust, her tight little arsehole milks every drop from me.

After what feels like minutes, my blood starts to re-divert back around my body. I pull out, and Katie turns and kisses me. This was softer than any of our previous kisses. "Thank you for being so considerate; we have time for a shower, but he'll be home soon."

We took a shower together, allowing our hands to tease one another, but neither of us pressed too far. I left shortly afterward with a massive smile on my face and a limp in my step. I couldn't quite believe I was hard again.

Later that day, I got a message from Katie. It was a picture of her naked in front of the dresser. Her buttocks were redder than I had anticipated. The message read, "I have smiled every time I've sat down today," shortly followed by, "Next time, it's one of your fantasies."

That was how Katie and I met; we have been each other's dirty little secrets ever since.