Riding Coach

Paul could feel his heart pounding, moisture forming on his forehead, and fear rising rapidly as he glanced around for signs of being seen.

The woman to his right shifted around, turning around to face the back of the train, still lost in her conversation but turning in a direction that would very quickly reveal within her line of vision Paul's exposed cock.

He removed his left hand from the lady's bottom, reached down and retrieved his briefcase, and pressed it against his crotch, forcing the woman's hand away from him.

It was just in time. His sudden movement had caught the attention of the lady with the phone, who just briefly glanced at his briefcase, clutched against his body. The sight was trivial to her, barely making her conscious awareness. She described to the person she was talking to what she happened to be wearing that day. Apparently it was important for the other person to be aware of that.

The businesswoman though was not pleased. "Please, sir," she asserted, not at all quietly, "if you wouldn't mind, your briefcase is poking me in the back."

It wasn't really poking her there at all. If anything, it was poking her in the butt. But it was the more polite way to express her complaint, and it was one that any gentleman, any courteous commuter, really could not ignore, particularly as she began to force her hand behind the briefcase, trying to regain the steel rod she was holding onto before. It is particularly discourteous to deny a fellow passenger access to a rod.

Paul politely shifted the briefcase a bit to the right, but finding this rather awkward he took hold of it with his right hand and reached up to the bar with his left. The briefcase was now effectively lodged on his right side, providing ample coverage for his cock from any passenger to his right, particularly as he gripped it from the bottom and hugged it against his side and hip.

"Thank you so much, sir," the businesswoman replied, smiling gratefully and mischievously, as she regained control of his exposed stiff cock. "That's much better, and very courteous of you."

Paul could feel his heart pounding. Here he was, standing in a crowded, public subway car, deep in the process of the morning commute, and his cock sticking out of hs pants, like he wanted to expose himself to one of the other passengers on the train. Just saying that word to himself, "exposed," caused his heart to flutter. Imagine the embarrassment, the shame, in getting arrested for indecent exposure. This was the kind of thing you would surely get arrested for: your hard cock sticking out of your pants on crowded public transportation. It was the kind of thing that might even make the newspaper, only the local section to be sure, and even still only a minor, brief story, but one nonetheless that most everybody would read; some finding it amusing, this ridiculous pervert exposing himself on a public train. But, others would be appalled, and certainly those who knew him. What was he thinking? This would be difficult to explain to his employer, to his relatives, or to a future girlfriend, if she somehow discovered the truth of his history. He wondered if they post on the web names of persons arrested for indecent exposure, like they do for other sex crimes. Geeeeez, this wasn't good. This was indeed a very, very risky and dangerous thing to do, yet he continued to let the woman in front of him handle and stroke his exposed stiff dick.

It is never easy to resist or argue with a woman who has your hard naked cock in her hand. She does indeed literally have the upper hand, and it just feels so darned good on your cock. Why deny her anything, when she can provide you with so much?

"What are you doing?" was all he could muster. It seemed rather obvious what she was doing, but he was really asking whether she realized the risk of what she was doing.

She continued to look back over her shoulder, smiling mischievously yet otherwise still acting all the while so innocent and naive as to what she was doing, all the while sweetly fondling his stiffness, softly circling the tip of his dick with her thumb. "Doesn't he feel better out in the open air? He can't like being all cooped up inside, can he?"

The train suddenly began to lurch and rumble as it pulled into a station.

His eyes grew frightened, and sweat began to seep from his pours. This was not good. This was not good at all!

Yet, the woman did not appear at all concerned. She did though turn her face forward, watching calmly as passengers maneuvered into position to leap from the train once the door opened, squeezing and pushing by those who were remaining on board.

Paul looked around in panic, double-checking, then triple-checking to be certain that his briefcase was effectively hiding him. And, his heart sank as the man to his right pushed and squeezed around the woman to his front right to get off the train. She essentially took his position, the phone still attached to her ear. Paul shoved up against the soft, round butt of the businesswoman, even bringing his left hand down off the steel bar to clutch her waist, holding her body, her bottom, against him, ensuring that nobody getting on the train could possibly separate them. It was a desperate move out of concern and fright, but also a desperate time, as well as a wonderful time and place for his hard dick, now rubbing against the lady's soft round rump.

He, or more accurately his cock, could hide even more effectively if he slipped it under her skirt, but it was such a tight and long skirt that this was simply not a realistic option. The woman instead held, fondled, and stroked him, trying to reassure the frightened dick that everything would be all right, or at least was most likely to be all right.

Still, it was relatively easy for her to remain calm. If anyone did notice she could claim that he was molesting her. She was not the one with an exposed cock.

Nevertheless, his dick was reassured by her hand, or at least it was pleased to be so deftly handled. As far as his cock was concerned everything was just fine. The situation might be highly risky, perhaps even foolhardy, but his dick could not forget the fact that he was being well stroked by an attractive woman. From the perspective of his cock, things really couldn't be much better, unless of course he could be lodged up inside her cunt.

Quite a number of persons did get on board. Paul tried to look calm, disinterested, and bored, like most every other morning commuter, all the time feeling the woman's hand continue to softly caress and fondle his stiff stick, now lodged tightly against her sweet ass.

He did not lose his erection. He was nervous, even scared, but it was not a self-conscious anxiousness that would normally impair and ultimately diminish his excitement. It was in fact an exhilarating anxiousness, the kind one experiences on a roller coaster, skydiving, or bungee jumping. It was an energizing, invigorating, thrilling anxiety that only added to his arousal, his excitement. He never felt more alive, more thrilled. His cock swelled and twitched in the woman's had, as if it actually wanted to leap from its hiding place and boldly expose itself to the people on the train. Yes, he could enjoy this club, very, very much.

"Paul? Paul Reed? Is that you? What are you doing on this train?" Paul's heart sank once again. It was Donna Anderson! She was a secretary for Sterling Cooper. They were a big advertising agency out of New York, and Donna worked at their LA branch. His company often did business with Sterling Cooper. Paul would occasionally come to their office across town, and he would invariably chat Donna up on each visit. She was really quite a dish, as were frankly all the girls at Sterling Cooper (see "Ad Men"). He often wondered if they hired them primarily on the basis of their looks. "What?" It wasn't a particularly informative or effective response. He let go of the woman's waist in front of him, grabbed hold of the bar above him, pressed his briefcase even closer against his body, as well as his dick against the businesswoman's butt.

Donna crowded in closer to him as well, taking the position of the woman who had shifted but, but not necessarily at her own choosing, as more and more persons were crowding in behind her. "Aren't you going the wrong way?"

Donna was almost a foot shorter than him, and as he looked down into those round hazel eyes, her morning perfume wafting up so wonderfully into his senses, he could not help but feel his dick swell with interest, and lust. He had not gone out of his way to chat with her while visiting Sterling Cooper for nothing. She was a really quite attractive woman, with an engaging smile, an innocent charm, and such nicely perky breasts.

He had many a time contemplated asking her out, but always failed to get sufficient nerve, or at least act quick enough. Just as he was about to broach the question she would get called away by a boss, his eyes longingly following her swaying, wriggling bottom as it slowly moved away in the distance, out of reach, out of touch. She though invariably looked back, smiled sweetly, and gave him a little wave of goodbye, not appearing to mind that she would invariably catch his eyes on her bottom. That had to be a good sign, didn't it? If a girl looks back as she walks away, isn't she telling you something?

The train lurched as it pulled away from the stop and Donna, her soft, round breasts in particular, fell into his arm holding the briefcase. "Oh my!" she exclaimed with some embarrassment at the indelicate, intimate contact. She smiled apologetically up at him. "I'm sorry," she said, as she reached up to grasp hold of one of the vertical steel rods, finding it a bit clumsy to reach up that high, making it all the more difficult to steady herself.

"It's fine, really," he replied, smiling back in reassurance, but also finding it hard not looking uncomfortable and concerned, as his exposed hardness was but a couple of feet from her eyes, her awareness. All that separated him from exposure was his briefcase.

Donna tried to move back, to give him more room, but it just wasn't possible, as further persons squeezed against her, pinning her against Paul. She would have to keep her breasts pressed against his body. She attempted to divert his, and her, attention away from the awkwardness of their close, intimate, physical contact. "You haven't answered my question, Paul. What are you doing on the Red line? Are you going to pay us a visit?" She kind of hoped so. Paul scrunched his briefcase up a bit higher, to further block Donna's downward view, but that shift resulted in a rather awkward way to be holding it, and the position in fact required scrunching his forearm and elbow under and against Donna's perky breasts. If he was a gentleman he would move his arm aside. He was providing further lift to her boobs, but it probably wasn't the case that she really wanted (or needed) that kind of help. "No, no," he explained. "No, I've got some other business."

"Oh, I'm so sorry. I kind of like your little visits." She had not previously been so open in her flirtation. Perhaps pressing her breasts against a man helped to disinhibit her tongue.

Nor had he ever noticed her being so openly flirtatious. This was certainly less unclear than simply waving goodbye to him. Although, of course, he might now be confusing her words with the feel of her soft breasts pressing against his arm. He also felt the hand of the woman in front of him softly work his cock. She was applying a far more explicit form of flirtation: squeezing, stroking, tickling, and fondling his hard, stiff, naked dick. That was well away from being unclear.

He returned Donna's smile and replied, "Yea, actually, yes, sure, so do I." Paul was, of course, very concerned, actually desperately fearful, of Donna discovering his exposed dick, but the hand of the woman, and his concomitant arousal, was also helpful in encouraging and motivating him to be a bit more assertive with Donna. It was like when he was little and his mother gave him encouraging words to ask a girl to dance at the elementary school party. He was so nervous, so insecure, but his mother's reassurance and, more to the point, a strong physical push, did eventually get him to take the plunge. Having your cock stroked as you speak to a girl is perhaps even more helpful in maximizing your interest, your motivation, to approach the girl, not that in this instance he could in fact get any closer.

"Well, if it's not to visit me....I mean, us, then what are you doing here?"

The train was lurching and shaking, and with each movement Donna was pressing and brushing her breasts against him, as if she was in fact trying to get him excited. On the one hand, she felt rather uncomfortable about that, finding it rather obviously bold, if not inappropriate. On the other hand, given that it was obviously unavoidable and the fault of the train rather than herself, perhaps it wasn't so bad after all. There is perhaps no better way to flirt with a guy than to press and rub your breasts against him. "Are you at least going to get off at my stop? You could walk me to work, you know." She was surprising even herself at how obviously flirtatious she was being. She had wondered why he never would ask her out. What did she have to do? Press her breasts against him? Apparently so.

Paul would really love to walk her to work, if he was understanding her correctly. But, of course, there was simply no way he could do that. Somehow he figured having his cock sticking out as he walked along the street would end pretty darned quickly her flirtation, and interest. "I've actually got an appointment at the, um, at a supply firm, in North Hollywood." He knew that Donna would get off at Santa Monica. Donna furrowed her brow and frowned, making her disappointment very clear. "Oh, I'm so sorry."

The woman in front of him gave him another squeeze and circled her thumb around and around the tip of his dick, caressing the smoothness, the moist slickness, of his curved round crown.

Was she trying to tell him something? Giving him some sort of hand signal? Or, was she just playing around with him, enjoying the awkward position he was in? His balls churned with her stimulation, and with the lovely sight and feel of Donna. "Well, um, I could, you know, stop by on the way back."

Donna smiled, and even now intentionally pressed her breasts harder against him, feeling her nipple stiffen with interest. "That would be nice. Maybe we could have lunch? I know a real nice little coffee shop." She knew that he liked coffee, or at least he was always asking her for coffee when he visited. She assumed that his meeting at the supply firm would last the morning. His meetings always did when he came to Sterling Cooper.

Paul was not planning on staying that long on this side of the city. Of course, he had no actual appointment at any supply firm, and had intended to simply turn around and get back to his own job once this ride was over. He was already going to be pretty late for work. Now he would have to leave early for lunch, providing enough time to get all the way back to this side of town to take her out for lunch, then probably be late in returning to his job after lunch. But, still, lunch with Donna would be worth the cost. "Yea, sure, sure, that would be fine. That would be great."

Donna smiled broadly, and leaned against him, resting and pressing her breasts against him. She wondered what his hand would feel like, if she placed her breast against his hand rather than his arm.

Paul wondered what it would feel like to press his hand against her breast. He wondered as well if he could actually feel her nipple stiffening against his arm. His own stiffness twitched in the businesswoman's hand as he contemplated the touch and feel of Donna's stiffening nipple.

Now that their lunch date was settled their talk momentarily drifted into inconsequential topics, the crowded trains being one of them. Paul knew that it would be best, more comfortable and polite, if he turned to face her, but he clearly couldn't do that. He did naturally though turn a little bit, but the woman in front discouraged any further movement by pulling back on his cock.

His heart was racing with excitement. It would be racing anyway with the thought that he had finally crossed the line with Donna. It wasn't, of course, a real date, but if the lunch went well, she obviously would want to go out with him. Her interest was now frankly obvious, albeit not as much perhaps as his erection. Crowded trains are at least good for literally pushing persons together. But, of course, his heart was racing for another reason, as he was also risking crossing the line in another matter. He recalled the Seinfeld episode when the guy on his first date with Elaine pulled it out. It was rather bold, and it clearly did not impress her.

His heart was also racing because his cock was so swollen, stiff, and out in the open, because it was being so wonderfully stroked and handled by the pretty businesswoman, who seemed to know pretty much how to handle a man's cock. She probably had a lot of experience in handling men as she rose within the ranks of the business world.

He even moved back a little to give her a bit more room and, frankly, to reduce suspicion. Donna might eventually wonder why his crotch was so tightly pushed up against the bottom of the woman in front of him. She couldn't actually see it, but by the position of the bodies it was rather clear that he had to be pressing against her. Still, she could hardly talk, given that she had her breasts pushed up against him.

There was something really quite nice about having your dick stroked while you flirt with a woman you're about to date for the first time. It was as if you were experiencing and anticipating the future both at the same time. His dick was yearning and straining for more rapid, intense stroking.

The businesswoman was not rushing things. She was not briskly moving her hand up and down his shaft. That would require too much involvement of her arm, and would be too readily detectable. Nevertheless, the slow, sensual stroking was itself pretty darned intense, pretty darned arousing. Paul could feel his balls tightening against his body, churning up a large serving of sloppy sticky cum, imagining that it was Donna fondling him as she talked with him about trivial, innocent matters, smiling up at him with those pretty hazel eyes, his nostrils basking in her perfume, his cock basking in "her" hand.

He asked, "Maybe you would like to go out to a movie, perhaps, sometime." As soon as he said it he was astonished. He could have waited for lunch to ask her out on a real date. That had certainly been his intention, but there was something about having his dick stroked that provided him with so much encouragement, incitement, and desire. He didn't want to wait till lunch to ask her out. Who would jerk him off there? The waitress was unlikely to do that. So, he just blurted it out, just like he felt he was about to blurt out something else.

"Paul, you're asking me out on a date?" She smiled teasingly at him, her eyes twinkling with delight.

He hadn't noticed before what pretty eyelashes she had. He had noticed a lot of other things about her, but this was the first time he appreciated how long, thick, dark, and fluttery were her lashes, how her rose eyeshadow was really very attractive, and her eyeliner so subtle yet effective. Her hazels eyes were really so pretty. "Um, yea, yea, I am." He felt he wanted to cum, so badly.

The business woman urged him more strongly, squeezing harder and now even jerking harder, for a brief moment pumping him furiously. Donna went up on her tip toes, leaned her face in closer to him, and as he brought his face down, she whispered, "I would like that very much."