An Evening Swirl

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."

Making my way through the parking lot and up the stairs I could feel the tinge of nervous energy flowing through my legs and arms. Most of the time I'd see that anxiety as a probable issue negatively affecting the rest of my day, however in this instance, and the similar ones before that it actually enhanced the high that I was feeling.

On her floor I was extra careful to knock on her door, not one of her neighbors. I was neurotically looking back and forth between the message she sent me earlier with her address and the apartment number next to her door.

I knocked lightly as not to disturb anyone else, then slightly harder when there was no response. When she still didn't open up I called her.

"Hello." She said in a quiet, sexy voice.

I felt my dick perk up as she spoke. "Hey, I'm right outside your door." I said almost whispering.

The sound of movement came from behind the door just before it squeaked and opened. Tanya's body was illuminated slightly from the dim stovetop light in the kitchen. Her curves were even better in person. I shuffled in trying to collect my nerves. She shut the door and we greeted each other with a hug.

"Hope I didn't startle you with the knock and then the call. Wasn't sure if you heard it or not." I rambled.

"I was in my bedroom watching tv so I never would have heard you." She chuckled.

Still holding each others sides I stood back a little to get a better look at her. She wore a long pink tank top. No pants. I couldn't feel any sort of waistband along her hips, but assumed she had short-shorts or maybe panties on underneath. Regardless I was trying to hold back my cock from growing anymore than it had. It wasn't presently obvious and I would have been embarrassed having her find out a hug and a sexy voice saying "hello" was all it took to make me throb.

"Want to watch tv?" She asked.

"Absolutely!" I replied.

Tanya led me back to her bedroom where the tv was already on. She climbed in on the left side and lay down while I walked over to the right, propping myself up on some pillows I leaned back. Some sort of crime solving, documentary-isn show played in the background while we talked.

I positioned myself close to her, but purposefully not right up against her. At the right moment I wanted to be able to ease into touching her. I've never felt comfortable being all over someone I had just met moments ago instantly, but with that being said it really only takes about ten minutes. In my experience if the conversation didn't lead to it, our combined horniness did.

We chatted about the site we met on and I told her about some of my experiences. I nonchalantly mentioned her enjoyment of younger guys and she told me about the 21 year old again. No details were given but she also mentioned two other guys around my age.

My urges were growing as we talked. I was fast approaching arousal level critical and the struggle to keep my hands to myself was becoming worse. In a moment of semi-rational thought I decided on a simple plan.

"The pictures you sent earlier were so sexy. You had me all turned on." I said quietly, my mouth close to her ear.

I slid one of my hands up her side and onto her stomach. The pink fabric of her tank top now the only thing between my hand and her soft skin. My hand wandered downwards slowly, over the fabric towards the bottom of the tank top, before then grazing over the bare skin of her leg.

She let out a slight whimper. "I thought the same about your pics..."

I continued massaging my hand up and down, teasing her sides with my finger tips. With every ascent I moved closer to her chest. Her big tits were outlined nicely in that top. As the friction from my hand traveled closer and closer with a light, teasing touch I could see her nipples starting to poke through more by the second.

Avoiding her nipples I continued to softly run my fingers up her sides and over her chest, then back down. Her soft whimpers were getting louder and just before it sounded as if they were going to turn into a moan I leaned over and kissed her. I slid my arm behind her head, still using my left to tease her. I felt her hand against my back as we continued to kiss, pulling me in closer.

Her lips felt incredible against mine. So soft and full. I knew they were going to feel even better all over me. I undid the rest of the buttons on my shirt while we continued to kiss. My hand then rested on her leg for a few moments before pushing tenderly upwards, this time slipping underneath her tank top.

It was just a few moments before my hand was exploring the soft skin near her hips that I realized she didn't have anything on underneath that pink top. I almost let out a moan at the realization of it. The pulse of my cock accelerated as I thought about how she opened the door for me with no panties on as I continued to kiss her lips and my hand was reaching her wonderful chest.

My kisses moved towards her neck as I teased her chest. Eager to remove my obstacle I took one last deep kiss into her neck before sitting up to first remove my shirt. I was kneeling over her as her hands began to rub my stomach and chest. She smiled as she looked up at me.

"Sit up for a second." I muttered in a sly tone.

As Tanya sat up I reached up underneath her tank top, pulling it over her head slowly so I could take in her sexy body, and those beautifully busty breasts. In the meantime my cock had become completely engorged. I could feel it throbbing as it pulsed against the fabric of my jeans. I unbuttoned the fly and top button to allow for some more breathing room as I leaned in for another tongue kiss. I climbed on top of her curvy, naked body kissing her lips, then moving back to her neck.

When I finally made it to her chest I was in heaven. Tasting her soft, dark skin while her moans filled the room was an incredible feeling. I kissed her chest all over. I grabbed her breasts from the sides, one in each hand and pushed them together as my lips kissed and explored around her nipples.

"Do you like your nipples sucked baby?" I muttered in a breathy tone between kissed.

"Mmmmm yes babyyyy, suck them." She moaned.

I positioned myself above her right breast. Lightly at first, I started to swirl my tongue around her erect nipple. I kept swirling as she moaned before beginning to wrap my lips around it. As my tongue continued I began to suck, lightly at first and then applying a little more pressure with each second. I teased her with the set up of this a few times before finally diving all the way in.

I took my time on her chest. There was nothing like teasing, kissing, grabbing, and sucking a beautiful pair of breasts like Tanya's. It was an act that somehow managed to fed and ease my horniness at the same time.

Almost reluctant to leave her beautiful chest I knew it was time to make my way further down her body. I kissed her stomach as my fingers slid teasingly down her sides. My body moved further down the bed and I found myself with my head between Tanya's legs. Her velvet skinned inner thighs on either side of me, waiting for the touch of my lips and tongue, both leading to her sweet, shaved, pink pussy.

Inner thigh kisses get her going right away. Soft, light ones would make her whimper, and the occasional deeper, more tongue heavy ones planted when she wasn't expecting it would illicit a moan while her legs would push closer as her body pulsed. As my face drew closer to her sweet, pink pussy I could see how wet she was. The light from the tv made it glisten.

I lightly tongue kissed around her lips; my shoulders underneath my thighs and my arms reaching up so my hands could take hold of her breasts. As her body began to pulse more frequently I took my first real taste of Tanya. My tongue eased up and down her pussy lips, swirling around slightly back and fourth, then moving to the bottom of her pussy and taking one more long lick, only this time slipping over her clit.

She pushed her pussy against my face as my tongue reached her clit. As she did so I very lightly wrapped my lips around Tanya's clit and sucked softly while my tongue began to massage it further. With her moans as my guide I carried on, picking up the pace little by little. I started teasing her chest and nipples again with my fingers, occasionally grabbing her tits when I applied a bit more pressure to her pussy.

Without warning her legs started aggressively wrapping around my head. A few seconds later the moans started and I felt her hand grabbing at my hair to push me against her pussy harder.

"Mmmmm more, moreeee!" She moaned.

My tongue was getting tired but I had to pull through. I sucked a little harder and swirled my tongue a tad faster as she yelled almost incoherently. "Fuck, just like that!"

The pulses became stronger and stronger as she came, grinding her pussy on me as the orgasm took over. I grabbed her breasts while her legs continued squeezing my head. As the moans subsided her body loosened, releasing me from her grasp. The loud yells were replaced with heavy breathing as she calmed.

I moved back up next to her and we kissed while she recovered. Once she caught her breath she pushed me onto my back. She kissed her way down my torso before getting to my waist.

"Lets get rid of these." She said, smiling naughtily.

She pulled down my jeans and boxers allowing my cock that had been throbbing almost since I had arrived to finally be free.

"Looks even prettier in person." She said with the same devilish smile.

Tanya wasted no time at all. The teasing, while brief, was all that was needed. When she wrapped her thick lips around the tip of my cock my body quivered. A quiver that continued as she slurped up every inch of me into her mouth and to her throat. She took a steady pace that felt incredible.

Bobbing up and down on my throbbing cock she looked right in my eyes. What a great sight it was. As she moved back up she did something I had never experienced to this degree or intensity before. With her lips around the head of my cock she sucked in and her tongue frantically swirled around underneath the tip of my cock. I jumped as I sort of moaned and sort of yelped at the same time.

It felt so good and hurt simultaneously. To this day I've never experienced anything like it. She would do this abruptly in between gliding those luscious lips up and down my cock. Each time she did it was for a little bit longer than the last, or so it felt like anyway. If she did it for an extended period of time I think she would inevitably get an orgasm out of me, but I don't actually know for sure.

As her lips released from around my cock our eyes met yet again and she said "You ready to fuck?"

I got up and grabbed a condom while Tanya positioned herself in doggie style. Her ass looked so good that way. Even better than I thought it would from the picture. I gave her ass a firm smack before getting myself in position. With one hand spreading her ass cheek and the other on my cock, as to rub the tip against her pussy lips, I slowly started to ease inside her.