Streamray - What Does Video Sex Chat Mean?

Note: Another in an ongoing series documenting my (sometimes) interesting sex life. I arrived at the bar early, uncharacteristic for me on first dates. Its always best to keep the girl waiting, give the impression that you have something more important to do. However, for reasons of work, boredom, and my consistent desire to make rules, and then bend and eventually break them - I showed up early and started with whiskey. She and I had messaged back and forth a few times about standard topics, and agreed to meet. I picked her mostly because she had a bit more edge to her in photographs than other girls. If you're looking for what I'm looking for, small details in the picture - tattoos, booze - are a dead giveaway that she won't be the type of girl occupying a spot at my family's thanksgiving table. We messaged briefly about work - she was a recent grad working at a design firm. A few terse messages later I suggested drinks at a bar in Hell's Kitchen, about halfway between my office and my apartment. I'd just ordered my second whiskey when she tapped me on the shoulder. "Hi, I'm Carrie." I introduced myself - she was palpably nervous. They all are at this stage of the game. She ordered an Appletini, and I started in on my second whiskey, but my heart was beating extra fast - she wasn't dressed for Thanksgiving dinner. Her dress was a midnight blue with a black lace cutout, down to just above her knees. She was thin, but not quite petite, about ', with thick and (clearly curled) brown hair, bordering on chestnut. She had a thin face, angular nose, fair skin and quite piercing green eyes. If I had to guess I would say black underwear, shaved, possibly waxed pussy, and C-cup breasts, but for some reason I'm horrible at judging those. "So what do you think of the whole online dating scene?" I said. "I think we're lucky to be in New York - can you imagine doing this in Nebraska?" "That's true. You must do pretty well though, I can't imagine many people swipe left." "Oh sure, but only the psychos and the serial killers swipe right." Her voice had that playful hint in it that indicated it would at least be a conversationally interesting evening, if not a successful one otherwise. She was wearing black heels and no tights. She got up briefly to go to the back of the bar to head to the bathroom, and as I watched her walk away, I became keenly aware of my cock and how it felt. I try to make it practice to not masturbate on days when I think I might fuck - but this morning I couldn't control myself and had blown a groaning load in the shower. When she returned, we ordered rounds two and three (four for me). I'd had a big lunch at work and luckily that was providing some insulation - she on the other hand, was visibly tipsy. The conversation moved to past relationships. We each talked about our longest and what had caused it to break up. The next conversational transition was an easy one - asking if she'd ever broken up with anyone because of bad sex. The conversation had gotten tense - I asked what her definition of bad was. "I guess to me, a big element of sex is about power - when I was a senior in high school, I wasn't super popular. Near the end of the year, I found out a freshmen had a crush on me and we ended up at the same party together. There was a bunch of drinking and we ended up back at his parent's house - he was a virgin. The look on his face when we first had sex was incredible - I don't think I'll ever forget that." At this point, just her talking was making my heart race and my cock swell further. I shifted in my seat. I asked her if she'd ever worked that into fantasies or role playing. This was the gambit - the transition from talking about past sexual history to possible upcoming sexual history. "What do you mean?" she said, her tone slightly accusatory - but also inquisitive. "There are a lot of ways to play out those sorts of things - power fantasies. Not like you wearing a leather suit with a whip. More subtle ways." Our discussion continued along these lines - and by this point, I realized I was probably in. Most women will bow out of such discussions or avoid them if they're not interested in going home with someone - she clearly was. When I made the suggestion that we move to my apartment, she agreed, using the same tone of voice that all girls use in this situation, as if she wanted to say it, but she didn't want anyone else to hear her say it, but she didn't want me to know that she was embarrassed about saying it. It's a fine balance. As we left the bar I put my arm around her waist to guide her out the door. This, really was just a mechanism for me to judge how comfortable she was with touch - and the fact that she didn't shy away at all meant we were good. My hand found hers. "Ohhhh Mr. Suave," she said mockingly. We continuned bantering the entire way we got back to my place. The conversation had turned back to the edge it had before, with her asking whether this was my standard procedure with everyone. "Yes, you are the twenty fourth this week." I said as she laughed. I didn't reveal that it was actually the fourth - the second at this bar. I'd started rotating when I realized the bartenders were starting to notice. Online dating allows a societal veil over the necessary regular sexual release of those in their twenties. Once in the elevator (easily the best place to make a move - the closing of the doors provides privacy, a transition, and a degree of finality). I gave her a very delicate kiss - not what she was expecting I think. The tension up to this point was pretty palpable and I think she expected I would go in for the aggressive make out. That's the key in building anticipation - when she thinks you're going to zig, you zag. I didn't even use my tongue, but made sure it made a good noise. That's a secret - the kiss has to sound good to the girl. No sense doing it silently - there's no way for them to think they're in a movie or a fantasy. She kissed me back, with more force, and I felt her hand slide up the back of my jacket. Her kisses were hungry and slightly Appletini tainted. The carresses along my back made my heart beat faster and my cock swell uncomfortably down my pant leg. I hadn't flipped it up before getting on the elevator, and now had an erection in the most annoying spot. As the elevator came to a halt, the door opened and there was another resident standing there as Carrie and I quickly parted. The resident, a girl I recognized from the building, averted her eyes - how nice of her. I led the way down the hallway and opened my door. Carrie began to have a basic look around as I went for the booze. "What would you like? I may switch it up." "What are you having?" "Gin and Tonic? Summer drink." I said, pulling down the round bottle of Hendrick's Gin. "Ooh that sounds good!" I even had the limes. Within five minutes we were comfortably ensconsced on the couch, legs touching and back to the type of conversation that we both wanted to be having. "So what's one of your dark secrets, Mr. Suave?" "I vote Republican." I said - provoking an eye roll from her. I can't remember ever seriously answering a girl's question on the first go-around. It's just not sporting. I began again, on a more serious note. "I enjoy having sex with clothing on." At this, her eyes widened and she flushed red. "Why is that?" "There's something about not even being able to control yourself to the point where you want it so badly you can't even remove clothing. I think the idea of teasing is important." At this point there was no holding it back. Carrie put her drink down and reached across to me. We began to kiss and for the first time, I felt the lace of her dress. It was a coarse material and had a backing to it. I ran my hands up her back symmetrically and found the skin of her back and shoulders, and up to the back of her head, through the thick of her chestnut hair. Our kisses had become deep now and the smacking sounds were punctuated by deep breathing out our noses. Her hands had wandered down and her left hand slowly stroked my swollen cock while her right was undoing my belt. I moved to her ear and neck and took a deep breath of her perfume - a mix of floral and citrus - and just savored the moment of taking in a girls scent, how intoxicating it was - and knowing that soon I would smell and taste her pussy. She had completely undone my suit pants and pulled them down far enough to expose my boxers at my crotch. She pulled those down as well as I leaned back into the corner of the couch. Expertly, she lifted the waistband and freed me. The first moment a man's cock is let out of his pants - especially erect - is fantastic. She flipped her hair to the side and gently wrapped her left hand around me and began licking. Her technique was very standard, long licks up and down, transitioning to bobbing, alternating with squeezes. I didn't want to cum - so I just laid back and enjoyed watching her. Her heels lay on the floor next to the couch and her dress had cinched up at her waist. I had kicked off my pants and boxers. My right foot was resting on the floor and my left on the couch. I slowly caressed her hair as her head bobbed up and down. Her grip became stronger as her hands began to slide up and down my spit lubricated cock. The tension in my balls was growing by the minute. I reached into the end-table drawer and grabbed a condom. When she saw it - there was no visible reaction, so I tore it open and she stopped momentarilly as I rolled it on. I stood up and unbuttoned my shirt and pulled my socks off. Carrie leaned back on the couch and I knelt between her legs and pushed the hem of her dress up revealing a black Victoria Secret thong with pale pink lace. I ran my finger from the waistband down to her pussy and roughly pulled it aside. Carrie's breathing had now become rapid as she knew what was about to happen. I scooted down and placed the head of my cock against her pussy. She had an "outie" labia, and the crotch of her panties was wet when I moved it aside. I only needed one rub to get enough to push inside her. "Ohhhhh." "Do you like that? Still have you panties on and everything." She moaned again as I thrusted a second time - and a third. I began to get into a rhythm and she flexed her knees up and leaned her head back. After a while, we changed positions, with me sitting on the couch and her riding me. The dirty talk began. "Oh Carrie, I want to cum on you so badly." "Where do you want to cum baby?" "I want to cum all over those panties." I pushed her lightly and pulled out of her, taking her by the hand and leading her to my bedroom. Walking with a full erection and a condom is something that cannot be accomplished gracefully, so I tried to do it as fast as possible. Once inside, I made quick work of her dress, leaving her (now somewhat disheveled) underwear on. When her dress came off, I could now see a small heart tattoo just above her right hip. She laid back on the bed and I pulled her underwear to the side. "Are you clean?" She said. "Yeah - are you on birth control?" (These conversations never go as orderly, or planned as anyone plans them to). "Yes." Removing the condom (always an odd task) with as much speed as I could muster, I penetrated her bareback. The difference of course, was monumental. I groaned audibly and didn't thrust for a second, just savoring the warm slipperiness of her pussy. My first stroke was slow, and then slow again. And then, I pulled all the way out, and pushed back in. It's never like the first penetration, but great still. I started to gain speed and rhythm, but also realized that my ability to control my orgasm was a lot less. Her warm wetness just felt too good. "You want to cum on my panties?" She asked, half out of breath "Yes." Her eyes were half closed now - that bedroom look. Her thick hair was splayed out on one side of her head across my amber colored sheets. Her hair reminded me of spun copper and the curls that she so painstakingly put in were still visible. With each stroke and the building ache in my balls sent waves up her chest gently rocking her breasts back and forth. My breathing got faster and I had to make the decision whether to continue or slow down. "Fucking come all over my panties." She said, making the decision for me. As my orgasm began and I felt my load building, I pulled out quickly and began jerking myself. The first twitch came and I shot a straight stream of cum on to the front of the lace. My struggling groans were intermixed with attempts to catch my breath as two other ropes of cum covered her panties. After that, several more led to a thick stream of lumpy cum on the front of her panties and down into the crotch. Her hands, previously caressing her stomach, had moved down and began playing with my load. I kept jerking until the last. Cleanup was, of course, odd. I asked if she wanted to stay over, and she did. She removed her panties and I lent her a pair of boxers to sleep in. The next morning, as she was getting ready to leave, I noticed on the floor next to my bed were the cum stained panties. "Keep them." She said. Vvc