A First Time With An Older Man

My move to the opposite coast had been difficult and I was extremely lonely when I decided to try online dating. Making friends had been easy when I was in high school, or studying journalism in college. But, it was an entirely different world after school and I was struggling to find myself in my internship and in my new city.

At first, it had seemed so glamorous. Single, fabulous, 23 years old, and in one of the world's great cities. It had been glamorous until I started work. The closeknit, tight publication that I had dreamed of cutting my teeth and becoming a journalist in didn't exist. Rather, the arty little magazine felt more like a boiler room and the hyper-competitive atmosphere was off putting.

As ad revenues got harder to come by, journalism took a beating. The idea of collaboration and mentorship had faded behind a new reality - if you don't get page views, you don't keep your job. Consequently, we fought each other for stories, fought each other for the best interviews, and shared little more than disdain for each other. And our extremely low pay.

So, that year's office Christmas party was quite the shock. My dreams of journalism revolved around moving to a glamorous city, meeting a glamorous new best friend at work, and uncovering a story that would change the world (while dressed impeccably). That Christmas party, which was held at a pub a few blocks away from our office, was the exact opposite of how I'd dreamed. Comaraderie didn't exist on that staff. In its place, we had extremely competitive, spiteful people determined to undermine each other in the quest for job security.

Being told that "we all know you're a little kiss ass and that won't fly here in the bigs" was the final straw.

After the party, my walk to the subway was especially lonely. Surrounded by millions, yet I didn't have a single friend within a thousand miles. It was odd and disconcerting being surrounded by the bustle of a city, yet being totally alone. The anonymity was painful.

I rented a dingy basement from a married couple. It was far from the apartment of my dreams, but it was affordable enough that I could live alone and I had put some work into it and made it mine. But when I got home that night, it didn't feel like home. Rather, in my drunken, extremely lonely state, my basement suite seemed like a prison. I was surrounded by millions, but didn't know a soul because I never put myself out there to try and meet people. Rather, I was trapped in my basement, waiting for a world that didn't realize I existed to come to me.

And so that night, on a drunken, lonely whim, I decided to put myself out there and so I made a profile on a popular online dating site. Online dating didn't have a negative connotation to me. Lots of my friends had tried it and a few even found great relationships online. But I hadn't tried it. My high school boyfriend lasted well into my junior year, and when we broke up, I was determined to be free for my last year of college. But, I uploaded a few meticulously chosen pictures, wrote a profile, answered a few questions and then browsed through the site.

It was late and so I quickly passed out, but when I woke up the next morning (mercifully without a hangover), I remembered my profile. My first instinct was to log on and delete it, but after I made coffee, curiosity won out and I decided to log in. So I sat down on my couch with my laptop and logged in. 21 new messages.

Most of the messages were pretty bad and either extremely short, or rife with spelling errors. I'm not really trying to sound like a bitch, but I feel like if you can't bother to spell check your first message to someone, or write more than 'hi', you and I likely won't be a very good match. But hidden amongst the bad were a couple of great messages.

The best was from a man named Nathan. But he was a lot older and outside my normal dating range, so I tried to ignore it. But, after I logged out after replying to a couple of the messages I received, I couldn't stop thinking of his message. He was an amazing writer who wrote me several paragraphs about himself, his interests and things he found interesting about my profile. He loved great music, appreciated all the books and authors I loved, and basically sent me the perfect first message.

I resisted for almost an hour before I logged back in to reply to him. He was, after all, only 41, which was really only 18 years older than me, so maybe my old age range was a bad idea. The next time I logged in, he had written me a longer, even more eloquent reply, and so it went for over a week. We'd send each other two or three messages a day. His messages were always incredible, brilliantly worded and intensely evocative. And so, when he asked me to meet him for a drink, I said yes. I couldn't help being interested in the athletic older man with the great smile and amazing brain.

We chose to meet on a Thursday, just a few blocks away from where I lived. He was dressed perfectly in a great blazer and tailored trousers and he was taller than I expected. His profile said 6'2 (which I liked), but I thought that everyone online added three inches to their height. Not everyone does and he was a wonderful foot taller than me. I love tall, so he already had points in the plus column.

A drink turned into two and nearly two hours later, we were onto our fourth, yet it felt like no time had gone by. He was even more fascinating in person and quickly ended up with far more points than for just being tall. Freelancing journalism had turned into screenwriting, though he liked to travel at least four months of the year and had a habit of going to dangerous parts of the world right before wars break out. So, he kept going back to journalism, mainly out of a responsibility to show westerners what was happening.

When he confessed to being pretty drunk and suggested we go get sushi, I quickly agreed. Not only was I quite small so the booze really hit me on an empty stomach, but I didn't want my drink with him to end. And so I stood outside with him while he smoked a cigarette (his biggest negative) and waited for a cab.

"So, I've just got to tell you that you're way too young for me, but I think this is the best date that I've ever been on," his words caught me out of nowhere and stung a surprisingly sting. Way too young for him? I agreed this was the best date I had ever been on, but it was so good that the age which once concerned me was no longer an issue. It hurt to realize my age was the real issue.

But the cab arrived and he returned to the gregarious, fascinating man I was so into and I quickly forgot about being way too young. We laughed most of the way to the restaurant he suggested as he regaled me with amazing stories from the road. He had lived a ton of life in only 41 years and seemed a little larger than life.

So much larger than life that I wasn't even remotely shocked when he seemed to know all the staff at the restaurant and spoke to them in Japanese. If anyone would know Japanese well enough to break it out in restaurants, it was Nathan. When we sat down, I asked him about it and he told me about teaching English in Japan to pay off some student debt and then getting his first journalism job there.

The waitress brought us sake and beers, then the food started coming. At first, I knew I was pretty drunk and didn't want to drink much more, but the food was amazing and full of flavor, so I kept drinking along with him. By the time our dinner was finished, I was a bad combination of totally smitten with him and drunk.

And so, when he invited me back to his place, I didn't even have to think before I said yes. Too young for him faded away as we waited outside for a cab. His smoking didn't even remotely bother me.

The cab ride was short, and we spent the whole ride holding hands in complete silence. It wasn't an awkward silence, rather it was the type of silence that happens when two people are excited for what will come at their final destination.

His building had a doorman and Nathan greeted him jovially and introduced me as his friend, Natalie. We stepped into the elevator, he pressed a button and we kissed for the first time as the elevator door closed behind us. Our lips felt electric and the kiss was altogether too brief, but we stopped when we heard the elevator door open to signify we were on his floor.

His condo was incredible and in a different mood, I would have been more interested in taking a look around, but that one kiss had primed me for more, and when he bent down to kiss me again, I eagerly kissed him back. There was a lot more tongue now and he kissed much more passionately than he did in the elevator. He led me through his condo, kissing passionately the whole time.

When we walked into his bedroom, he stopped kissing my lips for a moment and instead kissed my neck while he slowly traced his hands up and down my back. When he found the clasp to my dress, he paused for a second before unhooking it, unzipping my dress a little, and then letting it fall to the ground.

Dressed only in my bra and underwear, I flashed back to his words about being 'too young for him', but he started kissing my lips again and quickly drowned out my flashback. I was incredibly into him and helped him take off his blazer, then held my hands on his shoulders while he undid his trousers and stepped out of them, then took off his shirt. We both got onto his bed and he made short work of my bra.

We were only in our underwear when he pushed me onto my back, then worked his way down and popped my left breast into his mouth. My breasts aren't very big, but my nipples are incredibly sensitive and he worked my left nipple like a pro while gently rubbing his hands over my stomach. He kissed down my stomach, oh so slowly. Teasing. So, so slowly until he reached my underwear.

He whispered, "I love these panties" while he pushed them down and quickly took them off. He positioned himself between my legs, slowly kissed up the inside of my legs and whispered, "I love your sexy little shaved pussy" before settling with his face in between my legs and gently kissing my labia.

Kisses turned into gentle licks, and gentle licks turned into a probing tongue, and that probing tongue quickly drove me absolutely wild. Easily the best oral I had ever received in my life, his tongue and his fingers worked me into a frenzy. Truly an expert, a few minutes in, I wanted to ask him to teach me how to masturbate because he was working my body better than I knew how to work it.

Within minutes, I was incredibly close to an orgasm, but he seemed to sense that and backed off until I calmed down a little. Then, he slid a finger back inside of me and started licking again, slowly getting closer and closer and closer to my clit until his tongue was right on it. His tongue flicked over me, I felt the pressure building in my body, and I was so close to an orgasm.....

Until he backed off again, held the finger inside of me totally still and lifted his head.

"How are you doing?" he asked.

"Oh god, so close," I whimpered back.

"I'm so hard...I want to be inside of you when you cum. Should I get a condom?" he asked.

"Yes please," I nodded incredibly excited at the prospect of having him inside of me.

"Get on your hands and knees," he commanded while he slid off his underwear, and leaned down to the drawer on his night table. I got a brief look at his hard cock - it was big, thick and curved up - and I liked what I saw. He quickly put on a condom...

"You're so good," he appraised, "I can't imagine how incredible you'll feel."

He positioned himself behind me and I felt him place the tip of his cock against me. I moaned when I felt him slide the tip inside of me. Then I kept moaning while he slid himself inside, so, so, so slowly. It felt so incredible as he filled me deeper and deeper.

"You're so fucking incredible," he grunted as he pulled out, then slid himself back inside again, deeper this time. Deeper was good and I let out a moan of encouragement. He started pulling himself out slowly, almost all the way out until just the tip was inside, then going faster and a little deeper when he thrusted inside. The rhythm was incredible and I loved the feeling of his strong hands holding my hips while he thrust himself in and out of me. Every thrust was more incredible than the last and I felt the pressure building up inside of me again.

"Reach underneath yourself and masturbate for me. I want you to cum for me," he commanded and I obeyed. I reached my right hand down and started rubbing myself while he thrust himself inside.

Within a few minutes, I whimpered, "I'm so fucking close." He started thrusting harder and faster, then grunted, "Cum for me.."

A few more thrusts from his perfect cock paired with my steady, intense rubbing and I did as he commanded. "I'm cumming," I announced while I felt my body tense up and my pussy tighten around him.

He just kept thrusting harder and harder as my orgasm ravaged my body. The immediate pleasure of it, the fullness, the incredible sense of it all drove me wild, so wild that I barely noticed him painfully ramming into my cervix with each intensely hard thrust.

He exclaimed, "I'm finishing," then gripped down on my hips, thrust a few more savage thrusts and then his body got incredibly stiff. He groaned almost like he was in pain when his body spasmed the first time. I knew that spasm was him launching sperm into the condom, which I hoped survived the rough passion of this. Then he spasmed again, again, and once more.

He held himself inside for a second, thrusting a little, and letting out tiny 'oooohs' before he finally pulled himself out. I collapsed and rolled onto my back and noticed the condom was still there. I felt tenderized, but still glowing from my incredible orgasm and I felt really safe being in bed with him then. My first experience with an older man had been incredible...