Against All Odds Pt. 01

My phone buzzed with a text. The obligatory girlfriend save, but I ignored it. I was having a great time. Then the band started to play. The Betty Bright Band was not my style of music, but Dave was right; oh man, can she sing. The whole production was off the charts. I asked him how he knew the band, and he said he worked in the industry and had helped the drummer out. Dave had a nice hash spliff. It was wonderful. After that, we sat there and soaked up the evening with the sounds coming from the stage and the stars coming out.

I was so relaxed. Dave was nervous and charming and made me laugh. I was in a chill space when his hand inched closer to mine. I went the rest of the way, and just like that, we were holding hands. My heart was thumping when he turned and looked at me and said, "You're so beautiful. It's almost hard to breathe," and then we kissed. It wasn't the best kiss I'd ever had, but it sent a fast and urgent ripple through my entire body. I was instantly aroused, and it shocked the fuck out of me. We both slowly opened our eyes as our lips parted, and his eyes were locked into mine. His erection was impossible to hide, but his eyes held a million things beyond just lust. I was smitten and nervously looked back to the band and tried to breathe. My nipples were rock hard, and my heart was beating in double time to the beat of the song. This was totally not expected. In that instant, I knew I wanted more, much more.

The rest of the night, it seemed like all the colors were brighter. A trick of the lights, I thought. I could smell everything more: Dave, the beer, the hash, the lake, and the people all around us. Everything felt more significant and more alive. We slowly just got closer together, and then Dave was holding me in his arms for the rest of the night. Lightly caressing my arms or softly kissing the back of my neck and just wrapping himself around me while I sat between his knees with the blanket covering my toes. I had never felt so embraced or safe in my entire life. It was a pleasant experience. Eventually, Betty sang her last song. We stood for the encore and clapped. It was a good concert. Dave said, "So, do you want to go backstage to the after-party?" I didn't want to make him feel weird, but I just wanted the moment to be with him, so I nervously said, "Only if you want or need to. I'd much rather just take a walk and enjoy the rest of the night."

Dave's eyes lit up, and his smile got big, and he replied: "That's fine with me, Melissa. Let's get out of here."

As we were walking away, we got to a secluded spot, and I stopped him, looked into his eyes and kissed him as deeply as I could. A much better kiss but the same explosion. Again, there was no denying his arousal, but when our lips parted, his eyes still told stories I wanted know more about. I hoped at that moment that he would take me back to his place. My phone buzzed again. I ignored it, and then Dave said, "Do you like Thai food? I know a good place near my loft and on the way to the trains."

"I'm starving, and I love Pad Thai," I said. I quickly texted Cathy, "Having a great time, going to eat ttyl."

The restaurant was small and funky. A little Thai woman manned the counter, and she was animated and hilarious. Dave got a table in the back, and without knowing it was a thing for me, he sat me on the seat, looking into the restaurant. I hate having my back at the door. Dave and the hostess, who was also our waitress, seemed to know each other, and they were both making each other laugh. She kept looking at me and smiling. Dave was smiling, so I was smiling as well.

We ate light, some Pad Thai, Chicken Satay and green curry that was a bit spicy for me, but Dave loved it, even as it made his head sweat. We were laughing, talking about nothing, but I did share more about where I was from and that my parents lived in a log house on a lake. He could see how much I loved my parents. He told me more about his small town, and we agreed the big city was a ton of fun, but one day, he would like to settle down in the country. That made me smile. I don't know why.

As we finished our drinks, I could tell Dave was nervous or maybe having second thoughts about me. We learned during our talks that he was ten years older than me. His career was taking off, and he was just getting out of a relationship he said was not for him. I was trying to keep smiling and worried he would let me down, take me to the train, end the night and never call me again.

"Melissa, I'm just going to be honest with you. I'm nervous and would usually be happy being with such a drop-dead gorgeous woman like you. But my stomach is churning right now." Here it comes, she thought. I was starting to be sad. I thought he liked me, and gawd, I totally wanted him. My desire was almost overpowering; then he continued, "My gut is telling me not to fuck this up. To take it slow. I've been trying to take it easy since I met you. It took everything I had not to call you the same day we met. The last thing I wanted was some older guy going all 'full court press' on the hot young girl." He was blushing, his eyes never leaving mine, my mouth was dry, and I was holding my breath. Then he said, "I can't tell you how much I want to take you back to my place. How much I want to kiss you, ravage you and be with you till the sun comes up." He paused, then said, "I'm so attracted to you it almost hurts. I wanted to play it cool and be all 'hard to get' Melissa. I know that's what some woman like, but I just can't do it." He then looked down, still blushing. He was bare, open and vulnerable. I could hear his heart beating. I blinked; my chest was thumping, my pussy was drenched, and my nipples were totally hard under my tank top. Thank God I still had the sweater on. I had full-on 'dry mouth' now, and my cheeks were flushed. When he looked up at me, I said ...

"Dave, please take me back to your place right now."

Melissa is Smitten

We walked quickly down the street holding hands while Dave told me about this section of the city. It was a sketchy area, but in recent years, condos had been sprouting skyward near the waterfront. This wave of gentrification was swallowing up old warehouses and industrial buildings left over from the early years when the area was known as the Distillery District. It was now a daytime mecca for film production companies, music and film post studios, web design firms, and any number of advertising houses peppered between the last vestiges of inner-city industrial companies. At night, it was just starting to become a hot spot catering to the younger condo culture with zero desire for cars, preferring to be Uber patrons and public transit junkies. The clack-clack of a streetcar rumbled by with sparks flying from the overhead power wires as they walked.

Dave lived in a loft at the very edge of the east-end housing projects that surrounded the area. His street was dark and dimly lit. The building was all white-washed brick affair with massive old windows. As we walked in, Dave said, "Yeah, the freight elevator only works sometimes, and it does like to get stuck mid-floor." We chose to walk up to the fifth floor on wooden stairs with the renovated paint already worn away on the center section of each step. I could see Dave was nervous and trying to go slow while, at the same time, we both knew what was coming.

As we reached the top of the stairs, Dave told me, "This used to be a shoe factory, and when it was renovated, I grabbed a top-floor corner unit. The windows had me the minute I saw them." We walked down the hallway, turning corners a couple of times. The old wooden floors creaked, and each door was painted blue in contrast with the contractors' white paint on the walls and in stark counterpoint to the old wooden ceiling. His loft was the furthest away from the main stairs, right by the back hall fire escape stairwell. He opened the door, and we walked in. I was met with high wooden ceilings and a very open but not massive loft. The entire wall was giant windows looking into the east. If we were looking west, we would have seen the downtown core of Skyscrapers. To the south, you could just see the edge of Condo town glowing over the lake.

It was a simple layout with a small living room just as you entered, then a table area, his studio office space and a small kitchen opposite the table. In the corner, there were these cool walls of old wood. You could see Dave was excited about his loft. "Yeah, they were going to tear those old walls down around the original staircase, but I asked them to keep them and put a door in. The whole space started as a thousand square feet. I thought it was huge, but once you put in the bedroom a small bathroom and add all the other things, it gets small. But I love it. Being on the top floor, I only have neighbors on the one wall by the kitchen and below me. The floors are not very soundproof, but everyone is cool."

I loved it the minute I walked in. It had a real vibe. Dave was a bit of a pack rate, but it was clean and funky, with cool lights accenting the outer brick walls, the old wooden ceilings and the three separate spaces that made up the loft's main living area. His couch was a classic folding futon frame, old wooden coffee table and other mismatched but oddly interesting stuff peppered the space. Dave poured us some red wine, and I snuck a bump in the washroom as I was hella nervous. The coke completely exploded my horniness, and I was trying to be patient, waiting for Dave to make a move. I was curious about the studio, and when I walked out, Dave had some chill downtempo electronic music playing on big speakers hanging from the ceiling. The sound filled the entire space. The lights were lower, and Dave just walked up to me as I stood in the middle of the living area, grabbed my wine glass and put it down on the table.

"You're so beautiful it's making my heart race. I just have to kiss you, Melissa." He then did just that, deeply with a passion that made my knees weak. My nipples were hard, and it felt like my whole body was blushing. He then started on my neck and, with a feather touch, my ears, while at the same time, his left hand explored my breasts, slowly circling my nipple while his right hand grabbed my ass, pulling my pussy into his obvious erection. I could hear both of our hearts beating wildly. A long sigh escaped my mouth as he pulled my tank top down and started sucking on my right nipple while his left hand softly pinched the other. Goosebumps exploded across my entire body as my breasts were an electrified, erogenous zone for me. I reached down and grabbed his hard cock. I could feel its size and heat. His body trembled. He stood up and looked deeply into my eyes; his blues were on fire. He took my hand, turned, and led me to the bedroom. I wanted his cock. I wanted all of him.

The bedroom was small, with a queen-sized bed dominating the room and one window looking south towards the lake and condo city. It cast enough glow to augment the small bedside light that he had a light reddish cloth thrown over it. It was hot in the room, I thought, but it could just be the moment. I was topless, nipples standing erect in the sexy light of the room. Dave took off his t-shirt, and even though he was edging into the dad bod territory, he was built like a jock, and he had the most wonderful soft chest hair. He had a manly man look to him, and it turned me on to no end. We embraced and kissed deeply. His chest pressed up against my breasts. It was now obviously urgent for both of us. I started to unbuckle his belt and went down on my knees to pull off his pants. He was commando, so his very hard cock popped out, twitching and throbbing. He was not porn-star huge, but not small either, bigger than average, girthy with length, but most of all, his cock was gorgeous. I have seen some dicks in my times, and they come in many weird and not-so-pretty shapes and sizes, but Dave's was perfectly pretty, everything balanced, and it looked delicious. He almost fell over when I grabbed the base and lowered my mouth over him. His cock twitched and swelled even more. I sucked while he groaned and shook. I could tell he was nearing an orgasm. He suddenly stopped me, pulled me to my feet and kissed me, with his tongue urgently exploring mine. I could feel his hard cock throb against me.

He then slowly undid my jeans, pulled them down, and took them off. We were both naked, and the room was hot. A slight sheen of sweat was starting to glisten on both our bodies. I was delirious and horny and wanted him inside me. I was holding his throbbing cock when he pushed me onto the bed, moved me to the middle and started kissing me. I could feel his cock against my pussy, my hips thrusting up, but he had different plans. He started kissing my neck, then he played with my breasts. Gently teasing my nipples until they were rock hard. He slowly kissed my stomach and continued his featherlight kisses all the way down to my inner thighs. He brushed over my pussy, and I could feel his hot breath pause, teasing me. I thrust up, but he started to kiss my other inner thigh. He was teasing me, and he knew it. I couldn't take much more. My entire body was buzzing. Then I felt his hot breath descend on my pussy with his tongue touching my lips, and I gasped. He confidently proceeded to make love to me with his mouth and tongue. After an eternity, he then started licking my clit super slow and then with some speed. He then paused and started again, always with a slight change-up in his approach, as if he was searching for what turned me on or what would make me cum.

Usually, with other guys at this point, I start to plan how I would fake it. I have girlfriends that would have already cum by what Dave was doing. They might even be on a second or third orgasm. I was so horny I had no thought of faking it with Dave. Not yet at least. What he was doing felt fucking amazing, and I didn't want him to stop. He didn't need to know that I had never had an orgasm with anyone but myself. No guy had ever made me come. Some had gotten close, going down on me. Cathy has come close, as a girl just knows how to lick a pussy, but I was cursed in seemingly being incapable of reaching orgasm with someone else. I had told no one except Cathy about this and had simply learned to be very good at faking orgasms. I still loved sex, and there was a massive amount of pleasure in reaching this plateau I seemed to get to. It was like an endless wave of over-the-top total horniness. A tantric wave that left me very satisfied. I just never came or had an orgasm unless it was by myself. Dave continued his very skilled attack on my soaking wet pussy. I was so close. I was on the edge like I'd never been with a man. I was fighting the urge to fake it. Dave was not a boy, and I was sure he might know it if I did that.

"Dave, I need you inside me. Please fuck me now," I said.

"I am not going to last long, even with a condom."

"I don't care; just fuck me, please, now!"

Dave kissed me deeply. I could taste myself on his lips, and his heartbeat was almost louder than the music playing on the other side of the wall. He put a condom on, grabbed his very hard thick cock and teased my pussy, rubbing my clit and not going any further. I was delirious. He started to lick my clit again, real slow, pushing my clit with a gentle pressure that drove me crazy. Then back to teasing me with his cock while we kissed. This back-and-forth was making me so horny. I was on a tantric plane like never before. Most men I had slept with would have been done long ago. It was then that I felt the head of Dave's hard cock push past resistance and into my pussy. It was the perfect stretch with discomfort quickly turning to pleasure.

I let out a huge moan and bucked my hips, wanting more, but he just held it there, slowly pulled out, and then back in. While he did this, he was peering into my eyes, and I could see the fire of passion in his. He was trembling, and his cock was twitching. Suddenly he pushed his cock deep inside me with one slow thrust, touching my cervix, and just held it there. I could feel his knob twitch and his shaft throb bigger. I thought he was going to cum. That was fine with me as I was on the intense side of the plateau and had goosebumps everywhere. Dave then slowly drew his stiff cock out and re-started his 'just a bit in and a bit out' thing. I was delirious and horny like fuck. My god, he knew what he was doing.

I pondered my big fake when he once again thrust all the way in, but this time he lifted his chest off me and then proceeded to grind his pelvis into my clit. This sent a shockwave through my body. While being deep inside me, without disconnecting this grind, he was able to pull his cock out about three inches and then back in, all while still grinding his pelvis into my clit. I'd never in my life experienced this. He was bumping and grinding his pelvis into my clit while his thick, hard-as-rock cock kept going in and out. With each thrust, he tried to go deeper, intensifying the pressure on my clit. I was throbbing madly and expecting him to cum at any moment, but he didn't. He would stop occasionally, keeping this this slow, deep pressure on me. Holy fuck did he have stamina.

Then I got quiet, which surprised me as that was a sign I was about to cum. Then it started. That rumble intensified from the lowest part of my body, almost the deepest part of my soul. My pussy was engorged and wet. Dave was relentless and was now being random with this thing he was doing, but each time it felt like he was going deeper, the pressure on my clit was overpowering, an intense feeling was radiating from inside my pussy and then it happened. I exploded! The orgasm washed over me like a pleasure tsunami. I cried out, "I'm cumming, I'm cumming. Holy fuck I thought, I was having an orgasm! At that very moment, Dave's thrusting became urgent, and he went as deep as he could, and he also came. A loud groan with each thrust and twitch of his rock-hard cock deep into my pulsating pussy. I could feel each release. We were both drenched in sweat. Finally, he stopped, and we kissed deeply. I held him so tight with my arms while wrapping my legs around him, never wanting to let go. My pussy was still twitching and throbbing with the aftershock of the orgasm. I was dumbfounded, this older guy with a dad bod, thinning hair and not a porn cock had made me have my first-ever orgasm with anyone but myself. Holy fuck - I trembled with the hope this was not a one-time thing.

Dave pulled out slowly, groaning as he was obviously still sensitive, got rid of the very full condom and then flopped beside me. Leaning over and looking into my eyes, he said, "You're by far the sexiest and hottest woman I have ever slept with. That was hands down one of the best orgasms I have ever had," to which I smiled, kissed him and said "yea me too" all the while still reeling in the fact of what had just happened. For a moment, I thought that I should tell him, but I was too stunned to understand why it happened. I really wanted to see if it was a one-off. I wrapped my naked body over him, and we basked in the afterglow. I was happy when I played with his cock; it got rock hard again. We put another condom on, and he had this cool technique of putting lube in first.

I got on top and rode him while he played with my breasts. He then rolled me on my back, and for the second time in my life, after him slowly fucking me and licking me again, he did that bump and grind thing, and I exploded a second time! I was shocked. Dave did not come at the same time, so I rolled him on his back, stood up over him, squatted down in my cowgirl position facing him and rode his thick hard cock going all the way out and then all the way in. He was deep, and he felt terrific. My legs were screaming, but I didn't give up. I could tell Dave was getting harder. My nipples were jutting out; he grabbed both my breasts and exploded while I relentlessly fucked his cock in that position. My legs finally buckled, and I collapsed on his chest while he kept twitching inside me in the aftermath of his orgasm. We were both drenched in sweat; both had spent our fire and passion. He had a smile on his face that would not go away. I was still shocked, confused and really at a loss for words at that moment. I finally texted Cathy to tell her I was fine, she was pissed I had ignored her and worried, but I just told her I was stupid happy right now and spending the night at Dave's.