The year following a significant break up can be dealt with one of two ways, one can either succumb to the feelings of loss and wasted time, or one can spend as much time as possible bedding new partners to explore what you were missing while trapped in monogamy. I decided to choose the ladder, which given the recent popularity of online dating apps proved to be much easier than I had anticipated.
It had only taken me a little over a week to get back in the game; from there on out I just ran with it. If we fast forward about seven months ahead we get to one of my more memorable encounters. The actual, casual, dating that I had been partaking in was certainly fun, but it was missing elements of the thrill and risk involved in a one night stand.
Sex on the first date had happened much more than I ever could have expected that year, but the initial dinner, or drinks beforehand took away from the feeling I had gotten during previous experiences. These experiences usually consisted of meeting the woman who I had just started chatting with earlier that day at her place, then after a brief introduction stripping each others clothes off and fucking until one of us can't bear to go another round.
Having taken a few days off that week I seemed to fall into habits I hadn't since college, letting an adult dating site consume me for majority of my afternoon. It was mainly the usual B.S. chatroom experience that didn't go anywhere except for one woman in particular.
She was just shy of fifteen years my senior and didn't live too terribly far from me. The headline on her profile page read "slide right in." Naturally, I was instantly intrigued. Her main pic showed off a beautiful smile made by deliciously thick lips. The second would exhibit a lower back tattoo, leading to her fantastically shaped ass.
I had only gotten to enjoy one steamy experience with a black woman before when I had first joined the site years ago. It was a similar situation; she was about nine or ten years older and spur of the moment while chatting wanted to get together that night. There was something about a sexy black woman that drove me particularly wild.
Given my immediate attraction to her I decided to send a chat request. After a few minutes anxiously waiting a response she had finally entered the chat. The conversation started out with brief introductions, both of us keeping things respectful and vanilla despite the nature of the site.
Her responses were short-winded at first, but we seemed to click right away. We were both looking for a friend with benefits who lived locally which was a tough find on that site. As luck would have it, she was into younger guys; the first tidbit about her preferences that further accelerated my already moving arousal.
Whenever I expressed that "I loved older women" while chatting on that site, I had always hoped for the answer she gave.
"Have you been with guys younger than me?" I asked, unintentionally letting my voyeuristic side show.
"Twenty-one." She replied.
"How was he?" I fired back quickly.
"He was extremely nervous." She replied. "Started shaking as soon as we got in bed and the clothes began coming off."
Craving more detail I typed furiously, struggling to put the words together to form a readable sentence. The idea of her taking it from a younger guy had me wild.
"What happened next!? Did you calm him down? Was he throbbing for you?" I asked.
"I was patient and eventually got him to calm down. We went out to the living room and ended up putting a blanket down on the floor and thats where we played. First I sucked his dick. He was still shaking a little bit, but the pleasure distracted him from his anxiety. Then I pulled him on top of me and he fucked me until he came."
"Mmmmmm." I sent back.
"He didn't last very long but it felt good." She said.
"Sorry to pry for more details, that sort of thing gets me very turned on." I said.
"Its cool."
I just sat there for a minute and pictured what she had just described. My heart was racing and my cock was throbbing. At the time, this was a more recent find as far as things that turned me on. Hearing about it gave me an almost identical feeling to when I was younger and first experienced older women. I teased my cock as our conversation continued, just edging, not letting myself get too close.
We exchanged a few pics; no more nudes from her, but I got to see more of her very pretty face and those luscious lips. I sent a few shirtless pics as well as a cock pic.
"Mmmmm, that looks good." She replied. "How big is it?"
"About seven inches." I said. "Is that enough for you? I know a lot of the women on here want bigger."
"That's perfect." She said. "Its all in how you use it anyway."
"Glad you like!" I responded.
I was surprised that I had enough for her. Majority of the women I had chatted with in the past on that site wanted at least eight inches or more. I was actually sort of used to being told I wasn't big enough when I was on there. Hell, at this point it didn't bother me in the slightest.
After chatting a bit more we decided to exchange phone numbers. The messaging continued right away through text. We also finally told each other our names, which after exchanging nude photos and sex stories seemed to be the right thing to do.
Tanya was the center of my fantasies all afternoon. I wasn't able to get much else in the way of details about her with other young guys, but that one story was still sticking with me. As texting tapered off for a bit I used her pictures and that story to finish my edging session. That sweet release was enough to hold me for the next few hours.
"Hey, wyd?" Tanya messaged out of the blue that evening.
"Just chillin', bored and kinda horny." I replied.
"Same." She wrote back.
"Sounds like we should fix that." I said.
Just discussing the possibility of meeting was starting to make my cock fluff up. I stared intensely at my phone waiting for her response. The few minutes it took for her to respond felt like hours, I just sat unmoving until the text alert sound set me free.
"I'd be up for that." She said.
"Can you host?" I asked.
"Sure." She responded.
"Just shoot me your address and tell me what time to be there ;)." I said.
As the address came through I got even more excited. Meetings like this had only happened a handful of times in the past. Each one seemed to posses me with the most incredible high that would last from the moment I knew the encounter was happening, through the remainder of the day. It went beyond just horniness, more of a full body high.
My mind would obsess over the woman I was going to meet and every naughty detail I knew about her. It would gloss over pictures, stories, and sexts we had exchanged earlier as well as things I had imagined. That obsessing of course left my cock shifting between throbbing and slightly fluffed until the encounter.
I had about an hour and a half before I was expected at Tanya's apartment. I showered and styled my hair more meticulously than usual. Getting dressed I wrestled with the decision of whether or not to wear boxers before settling on wearing a pair. I figured it would give her one more thing to pull off of me, and for some reason I liked the idea. Jeans and a button down completed the ensemble.
The drive would only be about a half hour so I would be there with plenty of time to spare. Despite my best efforts focusing on music or talk radio was impossible. My mind kept picturing the endless possibilities of naughty fun we were about to have. I promised to start with long, deep strokes in and out of her pussy. I wanted her to feel my cock pulsing as I slide every inch of me inside her.
Our contrasting skin tones would look so fucking hot, I thought to myself. When she asked me earlier "if I had ever had black pussy before?" My cock felt like it was going to burst. I was honest and told her I had, although part of me wanted to tell her I hadn't. Something about that made me think if this was the first time my white cock would get to rejoice in the embrace of her sweet chocolate pussy it would be an even bigger turn on for the two of us.
Exiting the highway was when I realized I had to pay attention and snap out of my fantasies. What looked simple on the map was actually quite a maze of unexpected turns to get to her building. For the first time that night I stopped imagining Tanya's naked body and focused on the task at hand.
Shortly after finding her apartment building I was able to get a parking space. I was early, but only managed to wait a few minutes before texting her that I had arrived. The excitement that I blocked out while navigating my route from the highway was back with a vengeance.
"Hey, I know I'm a bit early, but I just parked." I said. I was beyond excited and very aroused. With each minute that went by I could feel my anxiety building as well.
About five minutes later she replied. "Just come up."
