Making the Most of a Situation

The train was an overnighter, from Milan to Naples, and on a Wednesday night in the middle of winter there was no shortage of empty cabins to choose from, even on the usually crowded second-class cars. I had flown in on a puddle jumper that went almost arbitrarily from Los Angeles to Chicago, Chicago to La Guardia, La Guardia to Gatwick and Gatwick to Milan. It was a cheap flight that cost me nearly 24 hours, and I wasn’t even at my destination of Naples, where my cousins were waiting for me for an extended visit. The nearly 12 hours of train travel that awaited me had only the appeal of being a pleasant change from the cramped plane seats I had been on.

I navigated the corridor until I found a cabin in the middle of a car that was farther from the front of the train, a strategy I thought would guarantee me some privacy and a quiet journey. I flagged a vendor from the platform and got a sandwich and half-liter of wine. The train began to move around 9pm and I was asleep before we reached our first stop.

At around midnight we stopped in Bologna. I dozed as people walked by the cabin, but fell asleep even before the train left again. I began to dream of vaguely sexual encounters, my imagination fueled by the beautiful women in Italy. The dreams stopped and started as I drifted in and out of sleep. During a longer stretch of smooth traveling, the pain of my throbbing erection straining at my jeans woke me just enough so that I reached down and adjusted it, pulling the head up and across my upper thigh and laying on my back to ease the pressure. I yawned once and blinked, clearing my eyes, and as I opened them I found myself looking into the eyes of a very attractive Italian woman, barely older than a girl in fact, probably in her early 20s. She had the exaggerated features that characterize the Mediterranean look, large dark eyes, high cheekbones on a round face, the extra padding on her curvaceous body concentrated in what appeared to be truly enormous breasts. Half-asleep as I was, I didn’t remember my erection and simply said, “ciao.”

She said “ciao” in a quiet voice and looked away immediately. I wondered why she had been so brusque and only then did I remember that my erection was probably quite visible through my jeans. I glanced down and confirmed my suspicion. My penis was in perfect relief, outlined as it was by the light that angled through the window and the tight sheen of my pants. It sloped gently up and to the left, thickening slightly and then continuing up in obvious arousal to well past the base of my left pocket. The head was swollen and the ridge created a noticeable line. A spot of moisture shone at the tip. Not wanting to draw any more attention to myself, I slid my overcoat over my body, making sure I covered my waist.

I ventured another look at the woman and noticed that she was fidgeting a little. Her skirt did not reach beyond her knees, and the white skin between her legs appeared and disappeared as she changed position. She appeared cold, and I commented that the heat didn’t work as well in second class cars. She laughed a little and we talked for a few minutes. She was going only as far as Rome, where her family was. She studied at the university in Milan, and was going home for a few days of rest between exams.

I offered her some of my wine and we continued talking for a while. She did not stop fidgeting and finally I asked her if she was ok. She complained that it was cold and that her sweater was packed at the bottom of her suitcase. I thought for a second, and then offered her my overcoat. She paused for a second, flashing a quick and slightly quizzical glance down to my crotch, then agreed and thanked me. I handed her my overcoat and she put it on. It was huge on her, but I noticed with some pleasure how tight the fabric was around her chest. She looked up again and said, “molto meglio.” Much better. I smiled and let my eyes linger on her chest. Even in the shadowy darkness I could see her blush, which I liked.

She asked what I did and I told her I was a photographer, spending some time in Naples for an assignment I’d gotten from a travel magazine. It was true, but I didn’t mention that this was my first paid assignment.

Her own gaze returned to my crotch before looking away. This surprised me a little, so I decided to make small adjustments in my position to see if she really had sized me up. I lifted a leg up on to the bench and rested on an elbow, a position that looks a lot more comfortable than it is but served the purpose of thrusting my cock between my thigh and pant leg to reveal its size and shape. I did a quick check and was happy enough with the effect: the shaft showed long and thick almost half way down my leg, the head a noticeable bulge and even my balls were somewhat defined by the seam of my jeans.

As we talked I noticed her looking out the window while she spoke, but each time she looked at me her eyes stopped for a nearly imperceptible glance at my cock. I was enjoying the tension that was rising between us, but the position I was in was becoming painful so I sat up. In a flash of creativity, I asked if she wanted to see some of my photography. She said she did, so I took a small album from my backpack, a collection of family and travel pictures I had taken over the past couple of years. They weren’t exceptional, but some were interesting and I had ulterior motives for wanting to show them to her.

I sat down to her right and we turned on a reading light to see the pictures by. With the album in my lap, I flipped slowly through the pictures, explaining who the subjects were and humbly apologizing for their poor quality. The light was weak so I adjusted my body and the album so she could see better. Each shift brought my crotch closer to the light and album. I realized that with one subtle shift it would be in plain view, but not too obvious. I lifted the album, adjusted slightly and let the album down again only two inches from where it had been. My cock twitched slightly as I realized how visible it was.

I flipped the page and we looked at some pictures of my last trip to Italy, the summer before. There were the usual pictures of fantastic scenery around Naples, some more artistically inspired ones of rock formations on Capri, and then some shots of myself and a few friends at the beach. We laughed at some of these, and she pointed at my “ridiculous” American swimsuit, the usual massive boxers that Italians despise, preferring to wear the Speedos that Americans find repulsive. As she pointed she pressed the album down onto my thigh and penis, evincing a slight gasp from me. She pulled her hand away quickly, then seemed almost to laugh. I asked what was funny, and she hummed and said, “oh… nothing.”

I didn’t let her off so easy, though, and said, “No, what, you can’t laugh at me without saying why.”

“Well,” she said, “I was thinking, maybe they don’t make your size.”

I looked at her and she looked back, then looked down at my cock. I smiled a little. Her hand was touching mine, resting along my thigh. I felt it move, pushing my hand slowly away. In a slow, drawn out motion she let each of her fingers come into contact with my shaft, slowly wrapping them over and around it until her hand held me firmly. Her hands were not small but there were still a few inches above her fingers toward the head. She began to stroke, softly and tentatively, coaxing my cock to erection. As I swelled she let out a quiet moan and squeezed.

I reached my arm around her and pulled the zipper of my overcoat down over her chest. She pressed my hand under her shirt and against her breast, and it was my turn to moan as I felt the incredible size of the soft warm globe.

She unbuttoned my fly and attempted to fish my cock out from my pants. Her fingers reached the base of the shaft through the hole of my boxers and tugged on it. Gradually, my cock appeared as a loop disappearing into my pants. Finally, the head popped out and it flexed up in a huge erection. Her eyes grew wide and her mouth opened slightly. “It is so beautiful,” she said.

I loved watching her stroke me, pulling the skin up and down the length and massaging the head with the palm of her other hand. I felt her breasts and squeezed her nipples in response. Her stroking became more aggressive as precum began to flow from my cock. I swelled and throbbed and moaned, loving how eager she was to make me cum but not wanting it to end.

I reached down and grabbed her hand, stopping her briefly while I pulled her shirt and bra over her head. Her breasts were huge and round, and her nipples pointed out in visible arousal. She pulled my cock up to them and touched the wet tip of my cock head to her nipples. My huge member was engulfed by her breasts as she wrapped them around me. I began to thrust into the hot crevice between her breasts. She held them close together, enjoying the sensation and obviously proud of her endowment. Her hand disappeared between her legs as I pumped more vigorously into her breasts, and I heard the unmistakable sound of her fingers plunging into a very wet vagina.

With a muffled cry she looked down at my shaft between her breasts and shuddered. The scent of feminine arousal was strong in the cabin. She pushed me back almost violently and held my cock straight up. She slid her skirt up her legs, pushed her panties to one side and straddled me. The image of her incredible body framed by the train window behind her, and my cock standing proudly between the shadows between her legs was so intense that for a second I wished I had my camera. That second passed when I felt her rubbing my cock head along her pussy lips, preparing both of us for what was coming.

I felt her gyrating, mashing herself down over my cock, and I felt myself sinking inside her, spreading her lips apart and opening her up inside. Half way down she began to shake and moan in stutters, and I leaned back to give her a better angle. The final few inches were a slow process of thrusts and twists, and when I felt her mound touch mine my cock head was just touching her cervix. Our fit was perfect and I began to thrust and stroke in harmony with her own passionate attempts to take yet more of me inside her. Her breasts swayed heavy and I sucked on her nipples at the apex of each thrust. The pace was quickening and I knew I couldn’t last much longer. I told her so, and she only increased the intensity, telling me “vieni, vieni.” Come, come.

And I did. I released an enormous jet deep inside her, feeling the cum escaping around my thrashing cock and spilling over my balls. I moaned deeply and grasped her breasts tightly as my orgasm intensified. I felt her squeeze her pussy tightly and sink down hard onto my cock, stimulating the head with wide gyrations. The cum flowed from me in long throbbing spurts. I moaned and my hips thrust of their own accord. Her own clenching began to flutter, and as I looked up at her I realized she was about to cum as well. My cock thickened in renewed arousal and I felt her orgasm at the moment it hit: a sharp spasm that traveled the length of her pussy. I was still cumming when she began to cry out in pleasure, a new sensation adding to the intensity as the moisture traveled down my cock and made a tighter friction. We came together now, thrusting and bucking until finally we both collapsed and lay in a sweaty pile.

I held her to me, keeping my cock embedded deep within her body.

When I awoke, the train was leaving the station in Rome. My overcoat covered my naked body. In spite of that, I wondered for a moment if I had dreamt the whole thing. I kicked myself for falling asleep, but as I remembered the events of the evening my cock sprang to life. As the train sped past the suburbs of Rome, an attractive older woman entered the cabin, put her luggage on the overhead rack and sat down across from me. She looked at me, glanced down to the tent that my erection made and, with a shy smile, said, “ciao.”