My first and only sex with a stranger, and it was on a subway...

    I’m a female who dates only occasionally due to my busy career. I don’t think I’m bad looking, but I don’t feel as if I get many passes made at me; perhaps I’m not sending out those kinds of vibes.

    However, a few years ago while riding on the subway to work (I live in New York), I caught a man looking me over from across the car. I didn’t think much of it, other than the fact that I thought he was reasonably handsome. He was dressed in a suit, and had nice shoes. I always notice the shoes.

    I looked away, but then glanced over again, can caught him looking at me once more. He glanced down immediately as if he was embarrassed to have been caught. Again, I didn’t think a lot about it, and after a while got off at my usual stop.

    Over the course of the next week, I discovered that he rode the same subway every day. I never saw him at night, but most mornings I ended up catching his eye, or his mine, and by the end of the week these staring exchanges ended with a faint smile on both our lips.

    It wasn’t long before I was picturing his face as I masturbated at night. I wasn’t obsessing, but it was a pleasant face and it served me well to envision him on top of me.

    After a while, I began to feel a little bolder when our eyes met, and our gazes held for a bit longer each morning. We didn’t say a word; our eyes simply locked for more than a few beats. I certainly didn’t deliver the Hollywood lip-licking come-hither look; not only is that just a silly fantasy but somehow I knew that would turn him away. This was far more real. I became more intrigued every day, and soon began to wonder when we’d do more than lock eyes.

    The way that happened surprised me a great deal.

    I had entered the subway car and was holding on to the hand strap, and began looking around for his now-familiar face. Not seeing him immediately, I decided this might be one of the rare days where we didn’t connect. I found myself disappointed. Our routine was becoming enjoyable and the anticipation of actually meeting him was beginning to feel a little intense. I began daydreaming of what our first time in bed might be like… I’m not normally prone to fantasizing a lot about sex, but somehow this stranger with a gaze was triggering an intense arousal inside me.

    What occurred next would normally have sent my handbag whipping upward in defense of my honor, but it happened so fast and I knew so quickly what was happening that I simply succumbed to the moment.

    A strong hand wrapped itself around my midsection while at the same time a body pressed against my back, although mostly what I could feel pressing into me was a hard ****. Instantly his face was next to my ear, and he whispered, “Don’t worry, it’s me.”

    Of course I already had known who it was.

    He then whispered, “I have a fantasy. I would just love to press against you here. To enjoy this before we have even really met. I know it’s a little crazy, but are you willing to indulge me?”

    I had to think for more than a few seconds, although with his arm about my waist, his warm breath next to my ear and his hard **** throbbing against me, I wasn’t going anywhere. My heart began to beat faster. I couldn’t help but wonder if I was getting myself involved with someone really strange. But at the same time, I felt the intensity of the eroticism. It was intriguing and different. We were in a public place, with someone I had seen for weeks, and so I decided I was reasonably safe enough. In reply, I moved against him ever so slightly back and forth. I heard his breath catch. He pulled me into him tighter. I knew I was getting wet, but I also knew that in this crowded subway car there was nothing I would be able to do about that!

    Soon my stop approached. The car door opened. He whispered, “go,” and pushed me gently toward the door. I turned to look at him, and he just nodded. I looked down at his pants, and could see a raging hard-on pressing against the front. He moved his briefcase to cover it up and gave me a smile.

    The next morning I took my usual spot, looking all over for him. For some reason, he never showed up. I found myself being intensely disappointed. I was intrigued, albeit a little confused, but mostly turned on, in a way I couldn’t explain or understand. I masturbated that night and had the most intense orgasm ever by envisioning him entering me while we rode in that subway car.

    The next morning, again, I looked for him all around. As if by magic, I felt his arm around my waist. He had appeared out of nowhere. He pulled me close the same way, and he once more whispered, “Let it be this way for a while.” All I could do was nod. A part of me wanted to break from him and turn around and ask him what the hell he was all about. But another part of me, and obviously the stronger one, decided to ride this erotic wave to its conclusion. Whether that would be crashing on a rocky beach or a gentle slide into paradise, I had no idea. Which is the excitement of it all, I suppose: the uncertainty. The danger. The unusualness. It all had me tingling in a way I had never experienced. Ultimately, I decided to ride this wave and just see where it washed ashore.

    I pushed against his ****. I could feel it even better than before. I surmised that he possibly wasn’t wearing any underwear this time, because I could feel more detail of its shape. It felt strong, and large, and very hard. I pressed back harder, moving every so gently against him, not wanting to be obvious as to what we were doing, but at the same time, not caring who might suspect.

    The stop came much too early. He gently pushed me forward while whispering, “Tomorrow, again. Wear something light.”

    It was springtime and getting warm, so wearing thin clothing was not going to be a problem. I did as he asked, carefully picking out a summer dress. I also chose a Victoria’s Secret thong that would’ve left nothing to the imagination had I not had the dress on.

    This time I saw him come through the door. His deep blue eyes nearly penetrated my brain, and my stomach jumped slightly.

    He walked toward me with a barely imperceptible nod and took his place at my back. His arm wrapped around me, and he drew me in. I don’t know how he got so hard between walking through the door and pressing himself up to me, but there it was, gently digging into my back, telling me that he desired me. Suddenly I wanted him in me. I knew that made no sense, and I knew we couldn’t do it there, but I desperately wanted that big **** deep inside my *****. I had never felt any desire like that in my life. I pushed harder against him, and my breathing quickened. I closed my eyes, because I didn’t want to see anyone looking at me. I didn’t care if they did, I just didn’t want to see them doing it.

    His hand strayed down to my hip, and he pressed harder. I wanted so badly to grab his ****, or flip up my dress and shove it inside me, but just the thought of it, and the eroticism of the moment, finally sent me over the edge. For the first time in my life, I had an orgasm without even touching my *****. It was all I could do not to scream out, or screw up my face. I looked down and gritted my teeth. I took a deep breath to mask it as best as I could. It was the most incredible feeling I’ve ever had. At that moment, I felt his **** pulse against my back, and I knew he was coming as well. I had no idea what he was going to do with a big wet stain on the front of his pants, but I didn’t care, and it added waves to the orgasm washing over me.

    I had just simultaneously come with a stranger on a crowded subway without even touching each other’s skin! I was completely blown away.

    I let him hold me while I gathered my breath and eventually opened my eyes. It appeared that most of the subway car’s occupants were either oblivious or didn’t care. I did notice one man seated across the way glancing toward us, but I didn’t care. It was amazing.

    My stop came up much too soon, and I reluctantly peeled away from him. His pants stuck to me slightly, and I could only hope there wasn’t a major cum stain on the back of my dress. I made a mental note to beeline for a restroom to check it out. As I exited the car, I glanced back at him, and he gave me the most beautiful warm smile and a little wave. I almost wondered what that meant, but I was glowing so thoroughly that I didn’t think much more about it. I just knew I was looking forward to the next day to see what it would bring.

    All that day and all that night I replayed the experience in my head. Talk about unique! I was intrigued and turned on, but of course, still wanted that hard **** deep inside me at some point. I wondered when the game would change and he’d ask me out. It was clear that he knew exactly what he was doing and I was more than happy to be in his charge, but I didn’t want to only have fully clothed sex with him forever.

    I can’t say if the ending to this story is happy or sad –I guess I have to settle for bittersweet– because I never saw him again. Every day I rode the subway, looking anxiously at all the faces. But his never appeared. I even rode the train past my stop, hoping to catch him somewhere. I rode it at night further down as well, hoping to spot him somewhere along the line. After I began walking the streets of Manhattan hoping to spot one man out of millions, I realized I was obsessing and left it alone.

    The thought of seeing him still haunts me to this day, although if I ever do, I may slap him as easily as press my body against him. I don’t know if he’s married and just does this on a lark, or if this was a one-time thrill for him, or if he rides the subway seeking this kind of adventure and once we both get off he goes after new prey… I have no idea. All I can tell you is that it was easily the most erotic experience of my life, and I will never forget it. If you’re out there, Mystery Man… I do still want you.