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Digital Dayz

Posted by: Age: 35+ Posted on: 9 comments
4 likes 27 views Category: Sex Stories Couples Tags: Internet, chat, chattroom, hotel, sex, meet-up, fwb

Just a little story about the first online "friend" I met and connected with in the early internet days


SO there was this time when… Back around the time the Internet made a mess all over the late 90s – early 2000s like a wad of Big League Chew makes on the face of young, inexperienced bubble blower, my side hustle was using my computer skills for good – well slightly. Both my main job and my “freelance” gigs had me traveling quite a bit, and often I would find myself either on the west coast or in Atlanta. Yeah… A-T-L so you already know where this story is headed. I’d been messing around with computers since high school but didn’t really get serious about them until college. Fast forward to after the internet bubble burst, which didn’t bother me because business was still booming, due to the part of the industry I chose to focus on. During the day I worked a boring corporate job, my girlfriend of four years had just dumped me, so there my young ass was sitting in my cloudy grey cubical hurt, hating my job, and horny. I poked around on the internet at the job, cause home internet wasn’t the greatest or the fasted so work was the best place to virtually explore the world. In my quest to be “unbored” at work, I stumbled across something called a “message board forum,” and there I found a few people casually chit-chatting with nicknames about unimportant topics of the day and other random nothingness. Day by day I found myself rushing to get my actual work done so that I could drown my misery with strangers by flirting, telling inappropriate jokes, and generally being anonymously silly online. This led to finding other sites to push the day by as quickly as possible and falling deeper and deeper into the world of sharing online. This eventually led to get-togethers, which then led to making some genuine friendships. One of those friendships happened in Atlanta. Still being new to the internet game but excited to allow my introverted self to shine, eventually, I ended up chatting with this honey one-on-one – I really wasn’t thinking about it at the time but this was about to open up a whole new world for me. What I did know though was that I had an A-T-L trip coming up soon, so maybe this might become a “thing.” Soon our online chats progressed from private messages to long-distance phone calls (thank goodness for the hood and the calling card scams). As it got closer to the date, I told LightEyes22 (not her real screen name but her eyes was her profile picture) that I had a wedding to attend in in her town and that I wanted to connect with her for a drink or just hanging out. Now I thought I was moving things, but what didn’t know was that things were moving to happen on the “Living the Single Life” message board that was my main home every day. The same weekend I was headed to “The A” and so were a few other chatters as it just so happened – great, perfect (sarcasm). Now if you remember, what also took place in chatrooms was that the thirst was very real, there always seemed to be a competition for the ladies amongst the dudes. I felt my place was solid with LightEyes so I was good, until I got to Atlanta and reality hit. The plan was to meet up with the chatroom crew after the rehearsal dinner. I took a taxi over to Justin’s for the meet-up, there was five of us there meeting face-to-face for the very first time; LightEyes22, BigMikeGoldie from Chicago, PinkyGirl, WonderWoman23 who was from New Jersey, and Me. The meet up was kind of awkward at first, the convo was nothing like it was when everyone was hiding behind a screen and a keyboard with quick fingers ready to talk shit. It was also weird between me and LightEyes even though we had talked much shit and flirted heavy online and over the phone. But after a while when everyone had at least one drink in them and began to feel more comfortable the conversation was almost identical to how we would chat on the message board – minus the innuendo and high-key flirts. It was more than clear that BigMike was angling for LightEyes but her eyes were on me, and the occasional hand on my leg under the table let me know that I really was good.  LightyEyes offered me a ride back to my hotel but she had to take Pinky, who was also from Atlanta, home first, and of course, BigMike wanted to roll. Mike was fixated on Light and could not take a hint that he wasn’t going to get anywhere with her. He might have had a shot with Pinky who seemed indifferent but might have been down had he took a shot. I guess he didn’t like her because she was short and plump (I noticed her plump titties too, her thick nipples made an appearance through her tight, sleeveless white turtle-neck every now and then). But really I think she was too dark for him, but I would have given it to her if I was in his position. After dropping Pinky off Mike, kinda gave me the look like he was gonna take his shot with Light and that I should fall back. I didn’t understand it, but online people socialized weirdly in real life (like feeling more comfortable calling each other by their screen name instead of their actual names), oh wasn’t really that different, but I don’t think I was that awkward. Maybe it was a Chicago thing, I was new to people from the Midwest at the time. So I fell back to the back seat and let him live, I was confident enough. “So Mike where’s your hotel again?” Light asked as she eyed me from the rearview mirror. He said something and then she asked me the same question. My hotel was downtown and she quickly decided that it would be better for her to take Mike first because he was in the opposite direction to where she lived. Just to be funny I said, “Yo Light, you can just drop me at my hotel first if you want.” She looked back at me like “really dude” and I smiled and held in my chuckle. Mike didn’t look too happy once we got to his hotel, I got out and gave him a pound, it was half-hearted on his part I smiled and told him later then jumped in the passenger seat. “Yo you know I can take a taxi from here right.” “Shut up, I’m driving out of my way to take you downtown so you better act right and stop playing.” I paused for a moment then realized what she was saying and then we both laughed. “So you came to the wedding without a date?” “I told you I didn’t have anyone to go with, that’s why I asked you.” “So would have taken me even though you never met me or seen me before?” “Yeah, it’s just a wedding date, not like a real date. I just need someone that I can laugh and bug out with, you know what I’m sayin’ someone I can have fun with, you know.” I said as I thickened my “New York accent” that Light told me sounded sexy to her. “Yeah, but what if I was ugly or like 500 pounds?” “I wasn’t worrying about that,” she smiled and blushed a bit. “Plus you ain’t sound like you was five-hund’ed pounds, you know.” In Justin’s I couldn’t really look at Light without seeming like I was staring and being rude to everyone else, but there in the car I could really check her out. Light-skinned thick girl, her lips were full and curved up slightly at each end, eyebrows were immaculate, dimples when she smiled – so cute. “Yo that dude Mike, wow he wasn’t trying to let me breathe, he was going for his.” “Yeah, I peeped that. Damn, your lips are really nice though,” okay that came out of nowhere, I was never one to just blurt out compliments like that but it was out there now. “Thank you, all my lips are nice,” she said to my surprise. As the awkward pause expanded past the first trimester she burst out a laugh, “you know I had to say that shit to fuck with you right.” “Yo you ain’t shit,” I laughed along with her, “oh so we gonna be on joke time now huh, okay I see how you doing.” “You know that was funny, but for real you the one with jokes, talking about dropping you off first. Was that some guy code shit or something?” “Nah, I just wasn’t trying to look like a playa-hata, you know.” “Damn there you go with that New York accent.” “Yo you know you just went past the hotel right, must be my accent.” “Dude don’t get cocky, I’m looking for parking.” “Oh okay.” At the hotel bar, we sipped on our drinks and her eyes were still on me with her bright smile and laughing at my jokes. “So you wanna come upstairs?” I asked during an elongated pause in our conversation. “Okay. Are we bringing the drinks.” “Well I’m done with mine unless you want another.” “I’m good, lead the way.” I paid and then we headed to the elevator. I pressed the sixth floor and leaned my back as the doors closed. As the glass elevator ascended I was torn between watching the lobby descend beneath us and pressing my lips on Light’s and sliding my tongue into her mouth. LightEyes made up my mind for me and immediately leaned her back on my chest and her ass on my groin. “Okay,” I said in a low voice and began to run my hands up the sides of her thick thighs, she then turned around, looked at me and then our lips met each other tongues instantly swirling against each other. The doors opened and we were still kissing but was able to stop before they closed. Once in the room, she took off her jacket and walked towards the bed where I had sat down. “Hey you know I wasn’t expecting all this, you know that right?” I said. “Oh, so all those late night conversations were all about establishing a friendship? Yeah right, besides how you know I wasn’t expecting all this?” I smiled and she straddled me placing her arms around my neck and began to kiss me again, my dick instantly regained its stiffness from the elevator and worked its way to get harder. In my head I could not wait to get her shirt off and see her nice, sizable breasts – had to be at least 34 D I guessed. I reached my hand under her shirt and popped her bra strap loose with one hand, a trick I’d perfected in college. She eased back, smiled and began to pull her shirt over her head. There they were, titties bigger than they looked and with a slightly lighter complexion. Her beautiful deep brown nipples were begging for my lips and I could not wait to taste them. “I couldn’t wait for this, shit I need this, mmmmm” she whispered as my lips felt the comforting warmness from her breast. “Damn girl, me too,” I answered between feeding myself, as placed my face back between her chest slowly kissing, licking, and caressing her soft bosom. It was like I felt each nipple grow firmer each time I had one between my lips, and when I slowly dragged my tongue around her areola and back to the nipple her moans sent chills to my loins. I wanted more of her but I also wanted her exactly how I had her, topless straddling me and my tongue all around her chest, nipple, neck, and back up to her lips. She began to kiss and suck my neck, her soft lips driving me crazy and she moved down my shoulders to my chest, knowing exactly what she was doing to me. She eased to her knees between my legs and began to unbuckle my belt. “I told you I’m a freak for sucking dick, but I think you thought I was joking or talking shit.” “Nah baby, not at all, go ‘head and get ya freak on.” She smiled at my corny joke, pulled down my pants and boxers then reached in for my stiffness. She smiled and began to stroke it making sure it was solid and standing straight up towards the ceiling (with a very slight curve). Her hands I remember getting a little stiff at the bar when she came from the bathroom and went in her bag for her lotion, (the things we think about when getting head). Her damn extra-soft hand on my chest as softly pushed me back. I laid back and she wrapped both her hands around my now throbbing dick and just held it for an extra moment before she put her sweet cushion lips on the tip of my helmet. When I felt the tip of her tongue wiggle and glide across the top, “shit,” I groaned and I could feel her smile as she locked her lips around my head and began to suck. She treated the head of my dick like it was candy, like an oversized sour apple Jolly Rancher that had her mouth juicy and had her slowly slurping and licking to melt me down. Her hands were steady around my hard shaft firmly in her grasp. I just knew she could feel my pulse thumping through the veins that were pressed against her the palms. What I loved about her technique was that besides the fact that she was really into the love of sucking, but it was that all of her attention was focused only on my thick dickhead and all the pre-cum that she was extracting from it directly onto her tongue. Next, she pulled her hands away and slowly eased most of me into her mouth, I could feel the back of her throat close and gag on the tip of my dick. She pulled her head back and then went down again, this time when she pulled back her lips and tongue were securely attached to me making my rod tremble like stressed iron. The soft pop sound that her lips made when my dick was released from them almost made me giggle but I was right back in her mouth and throat before I could substitute comedy for pleasure. She was making sure that I loved her lips and mouth. During the extended appreciation from her warm mouth, I felt her tongue slide up and down the underside of my shaft before she gently attacked my balls. “Mmmmmm shit,” I was in heaven and the more I moaned the more she applied her oral skill. I could not take it I knew I was about to cum, it was just a matter of time, up to this point, I had never had head like this is my life. I pulled her head away and stood her up to undo her jeans, once they were on the ground and around her ankles led her to the bed and laid her down. In those days I was such a boobie man and wasn’t really into going down on a woman (yeah I know, I know). So my mouth once again attacked her nipples. As I squeezed and sucked I began to move my hand on her neck, she moaned and arched her back, down her stomach to her sweet spot that I found to be a sticky pool between her legs. I noticed that the harder I sucked her nipples the higher she would arch her back and the louder she would moan. Her hand was on the back of my head roughing up my fresh cut but I could not stop her moans were driving me insane, that and her other hand stroking and rubbing all of my pre-cum around my hardness as I swirled her wetness around her clit. When my fingertips met her vagina all I felt was luscious softness and tremendously silky moisture. It felt like I was massaging Jello in a bowl of baby oil. Her clit was as firm as her nipples that I could not keep my lips off of. When I gently stroked her clit and began to circle it she moaned louder and arched into a squirm on the bed. Out of the corner of my eye I could see her begin to pinch the nipple I wasn’t sucking, this made my tongue lick the other nipple furiously. I could hear and feel her build up, then her other hand pressed the back of my head pressing me harder against her chest as her moans became silent. Suddenly, “oh shit, oh… oh shit, yes fuck yes, I’m cumming oh shit, I’m… oh, I’m…oh shit, OH, OH GOD, OH SHHHITTT, OH FUCK YES PLEASE DON’T STOP! OH SHIT, DON’T STOP! RIGHT, RIGHT THERE! FUCK SHIIITTT, DAMN, DAMN, damn, shit, damn, fuck! The amount of cream on my fingers was amazing, pulling my fingers apart and looking at the liquid webbing between them kept my stick solid. She was still writhing and moaning as I stood and went over to my bag. I reached in quickly shuffling my hand around for my condoms and then came back to her. I watched as she continued to play with her pussy, rubbing her clit to make herself cum again, I instinctually began to stroke myself as I stood beside the bed mesmerized – the veins in my dick were actually visually throbbing for her. She had me completely turned on like never before. She looked over at me and smiled, then motioned for me to come closer. She grabbed my dick and began sucking it again as she played with her wet pussy. I pulled away from her, wanting not to cum, and rolled the rubber down my shaft as far as it would go then began to move between her legs. She stopped me and again placed her hand on my chest pushing me to the bed. She reached down and grabbed my dick then guided into her dripping pussy. Straddling me again, “Mmm oh shit,” she moaned as she pushed me all the way inside of her. What I felt when I was deep inside of her was warmness and wetness with the tension of her insatiable pussy flexing tighter around me. My heavy arms were tight around her waist and then my hands moved down to grab her ass squeezing and pulling her in as she rode me. I could feel her ass clench around me as she moaned with her nails digging into my chest. I felt it rising again, I was about to cum, especially when she pushed herself down and ground her clit against the base of my dick and came again. “Ohhhhh, ohhhhh, shit, shit, oh shit baby, mmmm.” “MMmmm baby, keep cumming on this dick baby. Shit, you gonna make me cum, mmmm let that shit go,” I said, I could not wait to cum with her, I grabbed her ass harder and began to thrust up harder inside her as she continued to cum. So much wetness that I knew I was about to slide out of her but she held on. I knew she wanted me to cum her pussy was flexing tighter around me squeezing for my nut, but she would not let me cum. Instead, she got up, got on her hands and knees on the bed, she didn’t have to say a word, like a missile my dick slide into her pussy from behind and she moaned loudly again. I needed to cum now, I was aching damn near dizzy from the ecstasy she was throwing back on me –she was loving what she was doing to me. As I held on to her hips and pushed in deep, held, pulled back then pushed in deep again – held I would feel her pussy miraculously grip my dick each time I pulled back. Watching her pretty pinkness tighten around my dick and then disappear when I pushed in was amazing. Now I could feel it, I was about to cum, and she could feel it too. “That’s it baby, give it to me, give me that nut.” “AAAHHHGGGHHHHH,” I nutted as I pushed deep in her and collapsing my chest on her back twitching and shivering while continuously pumping my cum into the condom. I lifted back up still squeezing her hips, “oh shit girl, mmmmmffuckk! Damn aghhh shit, damn!” I collapsed again, this time on the bed beside her dick still inside her throbbing pussy. Her back on my chest, both moist and sticky from sweat, my energy drained but still hard, still a delayed twitch here and there. Our hearts were dancing in our chests like they were in a Missy Elliott video. She wanted round two, and so did I but I really needed a minute, or two and some cold ass water.

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