A Subway Adventure

A Subway Adventure

God, what was I thinking? My mind was racing, and I could feel the blood pumping through my veins by a rapidly beating heart while I tried to remain calm on the outside so as not to attract attention to myself, or more correctly, a version of myself that is not used to crowds in such confined spaces. "Fuck!" I screamed silently in my mind while I closed my eyes and tried to think of hiking in a cool forest, walking along a sandy beach on St. Maarten, skiing in the Alps, being anywhere but on a crowded subway platform in lower Manhattan as the clock had passed midnight and my imagined golden coach drawn by six pure white horses turned into a rotting orange pumpkin being nibbled on by several of New York's finest subway rats. I avoided eye contact while standing alone in lovely new 3-inch heels, nude stockings and a short, tight green mini dress that accentuated my "B" cup implants and slim legs. I may have looked sexy in the club that I went to with my friends at the end of the workweek, but I was not planning to be standing on a subway platform at this time of night mixing with regular people.

The trains were running slowly for some reason and the people kept coming down to the platform to wait for their chance to force their way onto trains heading into the darkness of Brooklyn. Normally I only dress like this when I go out as my slutty alter ego, René and have arranged for an Uber pickup or a ride with a friend who shares my secret. There was an unexpected turn of events tonight when my companion decided to take up with some dick and left me stranded. Uber had a one-hour backlog, so I convinced myself that I looked good enough to manage 15 minutes on the subway without causing a scene but delays on the New York City subway system added to tonight's perfect storm.

The slow-moving lights advancing toward the platform from the darkness of the tunnel warned of an approaching beast and people began to jockey for position at those areas of the platform with worn paint at the edge signifying heavy foot traffic where the doors of the subway cars were usually located. I had a wonderful spot directly in front of the soon to open train car doors and I felt the bodies of the other travelers press into me, particularly a gentle hand caressing one of my butt cheeks. I wanted to turn around to see who this rude excuse for a human being was but since we were so tightly packed and I wanted to avoid drawing unnecessary attention to myself, I decided to let them have their momentary cheap thrill while I continued my walk along the sandy beach in quiet solitude in my mind, and boarded the train without comment.

As the train began to move along the rails in fits and starts, I turned around so I could rest my back against the door to steady myself and observed a handsome young Hispanic man in his early thirties looking directly into my eyes. If this was the person who rubbed my butt a few minutes ago I would feel flattered although I would have been happier if he bought me a glass of wine first. I gave him a small smile simply to acknowledge the shared experience of an extremely crowded subway car while we both tried to maintain some dignity. He smiled back and leaned in to whisper, "I'm not trying to be rude but you look very nice."

"Thank you," I said quietly and glanced away while feeling excitement in my loins. The train leaned toward my side of the car and lurched to a stop. The crowd followed this motion and bodies squeezed a little tighter before everyone groaned and tried to find some space by gently moving arms and torsos while avoiding eye contact as much as possible. My gentleman admirer was pressed against me but was doing his best to allow me some room and quietly apologized for the intrusion into my personal space, "Excuse me miss, I seem to be another victim of circumstance but as soon as I can manage a few more inches I will give you more breathing room."

I inhaled deeply in an effort to claim a little more space and felt my breasts push against my neighbor in front of me, causing my nipples to become erect and my penis to begin to stiffen. "We are both trapped so I admit that options are limited but thank you," I replied with a small polite smile while wishing I could adjust my penis so it wouldn't stick straight out as I became aroused by the unwanted contact with a good-looking stranger. Simply thinking about adjusting my penis brought about the opposite effect and I could begin to feel an erection pushing against my lace panties. I looked off to my side and closed my eyes hoping that the distraction and darkness under my eyelids would work some magic; it did not and I could feel my dress getting tighter and knew that a very visible bump would be noticeable at the front of my dress if the crowd thinned at this point.

The train began to slowly move forward and the gentleman opposite me was forced backward allowing the back of his hand to rest on the head of my penis as it pushed forward against the material of my dress. I noticed a smile forming on the gentleman's face as he felt my stiff cock for the first time while remaining silent. I felt myself blushing and wished I could somehow transport myself to the bridge of the Enterprise with a simple, "Beam me up, Scotty," but no matter how many times I repeated the words in my head I remained on a stalled subway car on its way to Brooklyn. I smiled to myself at the absurdity of the situation and when I noticed the smile on my admirer's face I absentmindedly said, "Sorry."

"I could ask 'for what' but that would be impolite so I will conjure up my own version of a story to tell my friends another day," he replied quietly.

I laughed and responded, "I hope that we don't have the same friends since the embarrassment would kill me."

"If I see you in mixed company at some time in the future, I promise not to say a word if you agree to join me for lunch over the weekend."

"That's blackmail you know," I said with a grin.

"Yes, I know," he replied smiling.

I thought for a moment and finally said, "Very well then, you seem to have left me no choice so I accept your 'kind invitation'." With that, the train came to life and began to proceed to its ultimate destination, as if waiting for our negotiations to be completed before moving.

As we moved slowly from station to station, I smiled inwardly as I thought how well this gentleman played the cards he was dealt. He obviously knew that I was not female but was not deterred by that fact and might even have found it exciting. He knew that asking a stranger on the subway to go out for a drink would raise a red flag and lead nowhere under the best of circumstances, suggesting dinner would seem a bit too much and understanding that dinner involves meeting a stranger in the evening, in an unknown environment mixed with food and alcohol could be risky. But lunch tends to put people at ease, allows them to feel the comfort of other individuals milling around in daylight, light food and soft drinks are normal, and leaving immediately afterwards for another appointments, even a phony one, permits easy separation after the fact. Well played, my friend, well played.

"Is everything okay?" he asked. "You seem distracted and the way your brow is furrowed almost seems to indicate pain of some sort. Can I do something for you?"

"Oh, I'm fine, just temporarily got lost in thought. It's been a long week, and the subway is draining at this time of night," I replied.

"I understand but hopefully you will be home soon," he said with a caring smile. He reached into his jacket pocket and took out a business card that had the usual information and included a mobile number. "The next stop is mine and after you reconsider our lunch date, as I am confident that you will, please call my mobile number to confirm it. I'm free Saturday and Sunday and if I don't hear from you I will chalk the rejection up to experience, Ms.____?"

"René," I replied.

"It was a pleasure to meet you, René, and I look forward to seeing you again under more pleasant circumstances. Good night," he said as the train stopped at the station, the doors opened, and he walked away. My stop was next, so it was only a matter of minutes until I was above ground in the cool night air walking casually to my apartment. What started out as a miserable subway ride from Manhattan turned into a charming underground adventure.

Upon arriving home, I happily took off my heels and rubbed my sore feet before slipping out of my dress and underwear and putting on a soft satin robe. As I removed my makeup and got ready for bed, I found myself thinking about the fellow on the subway and wondered what he thought when the back of his hand inadvertently found its way to the head of the semi-hard penis creating a bulge in my mini dress. Clearly he wasn't bothered by it or maybe he hadn't noticed after all, which would add to my embarrassment when I had to tell him that the woman he was speaking with was actually a man becoming aroused by his accidental touch. I knew that I must be overthinking this and reasoned that in the end all I had to do was not confirm our lunch date and life would go on as before. I brushed my teeth, flicked off the light and crawled into bed holding my stiff cock.

Waking up a little after 10:00am the next morning, I found myself well rested and looking forward to a relaxing weekend, possibly a visit to the galleries in Soho and then maybe dinner in one of the small restaurants on the Brooklyn side of the East River near the Brooklyn Bridge. This was to be the 'me' weekend that I desperately needed; no rushing around, no appointments and no stress.

As I walked into the kitchen I noticed a business card on the dining area table that stopped me in my tracks: "Edouard Santiago--Vice-President". "Fuck!" I screamed in my head as I picked it up and fast-forwarded through certain parts of the night before. Why didn't I tell him thanks but no thanks when he suggested lunch rather than leaving it open? So what that he may have realized that I have a penis under my dress. This isn't the Middle Ages anymore and the subway doesn't run through Oklahoma, so why should I be embarrassed and agree to a lunch date just to buy his silence? On the other hand, he was polite, handsome and considerate so this chance meeting might be fate providing me with an opportunity to find a little happiness with a lifeform other than a cat. Stranger things have happened. Overthinking again!

I prepared a coffee while holding the card and decided to call him to propose meeting for brunch tomorrow, Sunday. Brunch is a little more formal and you can tell a lot about a person by the restaurants they select for any given event. Lunch could be burgers and beer but brunch implies Eggs Benedict and champagne. Edouard put some pressure on me by suggesting lunch and now I will test him by suggesting Sunday brunch. Ha, your move.

Edouard answered the phone on the third ring; reasonable, not hasty or casual, not someone waiting by the phone or someone who was prone to ignoring it either. "Good morning, Edouard. This is René, your fellow captive on the subway last night. I trust I haven't woken you," I said.

"No, not at all. I have been up for a while and I was just having coffee, scrolling through the news and wondering if I would hear from you," he replied.

"What did you conclude? Would I call you or not?" I answered with a bit of a laugh.

He laughed as well and replied, "You are a bit of an enigma, so it was hard to decide. On the surface you appear one way and underneath you are quite the opposite, so you are open to interpretation. Last night I firmly believed that you would call, mainly for your own reasons, and this morning I was not so sure, but I hoped that you would, mainly for my own reasons. Regardless of the reason that prompted you to make the call, I'm glad that you did."

We had a pleasant 20-minute conversation before he asked me about lunch. I thought I had stumped him with a brunch request but I was very pleasantly surprised when he responded, "What a wonderful idea! No promises but I will see about a reservation at Delmonico's, the birthplace of Eggs Benedict so we can pretend to be New York "old money". Give me your address and once I confirm a reservation, I will let you know when I will pick you up, unless you prefer the subway."

"Old money does not ride the iron horse on Sunday. I will send you a text with my address and phone number and look forward to seeing you in daylight," I said.

"Until Sunday, then. Goodbye, René."

After getting off the phone I suddenly had severe pangs of guilt. Edouard seems like such a nice guy and I felt so comfortable talking to him that I overlooked the most important point when I got excited about going to Delmonico's for brunch: does Edouard know that he will be taking a 29-year old man named Russell to an expensive brunch at Delmonico's thinking it is a 29-year-old female named René whom he probably hopes to get into bed? I could not be this duplicitous.

Edouard answered on the second ring this time, "Hi, René. Don't tell me you've changed your mind," he said jokingly.

"I haven't but I'm afraid you might. Edouard, I don't want to start off on the wrong foot by being dishonest with you. I think that you're a nice guy but feel that you proposed lunch because you had discovered something about me on the subway last night that you thought might embarrass me if it was made public. I joked about you blackmailing me so you would not publicize the fact and while we both laughed it off, I want a clear understanding with you about who I am. Edouard..."

"René, stop right there," he said. "I hear the change in your voice and I don't want you to upset yourself anymore. If you are going to tell me that you were not born a female, I know that. There were a few telltale signs that were obvious last night, but you come across as a very sweet person that I would like to know better. Pretending to blackmail you was a pretext to ask you out and we both know it. You and I are going out for brunch tomorrow and I will not accept an excuse so unless you tell me that you're an axe murderer, please be ready at 12:30pm since I have a 1:00pm reservation. No football jerseys or backward ball caps please. Is there anything else?"

"No, I guess not, you have summed up the situation perfectly. Thank you and I will see you tomorrow at 12:30pm."

I stared at the phone in my hand while wishing I proposed seeing him tonight. I wanted to feel his arms around me and his lips on mine while he stretched my sphincter with his stiff cock. Oh God, I am so horny right now. How will I last 24 hours and what if he doesn't want to come back here with me to fuck my brains out? You're getting ahead of yourself, slut. Take a breath!

I went for a walk in the park in the afternoon and ordered take-out Chinese for dinner before getting comfortable to watch an old film. There is something about black and white movies that is timeless and sexy even though some are a bit campy.

I also mentally planned my outfit for brunch, something chic and not too risqué, yet sexy enough to raise the temperature a couple of degrees. I picked a tailored navy pantsuit with a sheer beige blouse worn without a bra since the jacket draped nicely to cover my nipples while showing the curvature of my breasts. I wore matching navy heels with beige thigh-high stockings and light makeup so I looked 'afternoon elegant' or 'sophisticated sexy' whichever description you prefer. I hoped Edouard would take notice and be aroused enough to want to unwrap the package.

I got up Sunday morning and made a light breakfast with strong coffee before running a bath for a long soak. I shaved the areas of my body that required it and did my nails and makeup before getting dressed at a leisurely pace. I felt a bit nervous since it was after all a first date, but after speaking to Edouard the day before I did not have to worry about being found out as a male, something that always troubles me if the discovery was unplanned or unexpected.

I took the elevator to the lobby at 12:30 as agreed and Edouard was waiting in the lobby wearing a nice navy sport jacket over a sharp pale blue Polo shirt and Khaki dress slacks with tan loafers. He looked like he stepped out of GQ and I immediately wanted to skip brunch and take him back upstairs with me. I realized that I should have masturbated as part of my morning routine to relieve some of the tension I was feeling but since I could not go back to my apartment right now and stepping behind a potted plant for this purpose would be rude, I had to accept the tension.

As I walked up to him, he gently took hold of my shoulders and kissed me on both cheeks. "René you look beautiful and I feel very lucky to have been able to convince you to join me today," he said softly.

"You were very persuasive, Edouard, you have a way with words," I replied with a big smile.

"Dale Carnegie," he said with a laugh.

"I was thinking more Vito Corleone," I joked, and we laughed as we walked to car outside.

Arriving at Delmonico's in lower Manhattan, we were met by a suave looking gentleman who greeted Edouard by name. "Good afternoon, Mr. Santiago it is a pleasure to have you join us today. Good afternoon, Ms._____?"

"René," I replied softly.

"Ms. René, welcome to Delmonico's. I hope you will not be a stranger in our establishment in the future. This way please," and we were guided to a nice booth on the side of the dining room with a view to the front.

After settling in we received complimentary Mimosas and were given menus which we placed on the table while we toasted our chance meeting and a pleasant afternoon and then talked about lower Manhattan and its history. It wasn't long before I changed the subject to one more relevant to me personally. "Edouard, may I ask you a question?"

"Of course," he replied with a serious look on his face.

"After our talk yesterday, I began to wonder why you were inclined to ask me to lunch. Clearly you are a good-looking man and very gracious and polite as well which is a rare commodity these days, so why are you interested in someone like me if you know what I mean? You could have your pick of women in the City if you desired a woman, and probably gay men as well if that were your preference, but you accidently stumbled into a crossdresser and decided to ask her out. Is this a conscious choice or are you intrigued by the novelty?"

"I don't think classifying yourself as a novelty is a fair comment," he replied. "I try to keep an open mind and treat people as they warrant. If they are rude or obnoxious, I have no time for them. If people appear kind and genuine whoever they are, I react in a similar manner. It's a simple rule to live by and rarely complicates interactions with others. When we met on the subway Friday night, you came across as a frustrated but civilized person, someone willing to accommodate other people suffering the same fate even if circumstances made you uncomfortable for one reason or another. We shared a unique situation that many people would find embarrassing but you accepted it with grace and I felt compelled to go with the tone you set. I was drawn to you and wanted to get to know you better, hence my suggestion for lunch. Yes, I am intrigued by you but not specifically for the reason you suggest."

Before continuing our discussion, we ordered our brunch meal, Eggs Benedict and another Mimosa to keep the mood light. "So, it is not your intention to ply me with alcohol and then find some way to get me into bed?" I said with a sly smile.

Edouard thought for a moment before responding. "I wouldn't phrase it exactly like that, of course."

"How would you phrase it, Mr. Dale Carnegie?" I replied as I leaned back in my chair allowing my jacket to slip slightly off my left breast exposing the shadow of my nipple through the sheer fabric of the blouse.

"Hmm, I would keep up the light banter and after another Mimosa, suggest that we adjourn to my apartment to look at my etchings..."

"You're dating yourself Dorian, you need new material for the women of this century."

"Right.... adjourn to my apartment to look at my wall-to-wall flat screen TV and then seduce you with my charm," he said with a laugh.

"Okay, let's make this a pleasant afternoon free of tension. I understand your technique and your proposition, and I am prepared to accept your proposal if you remain a gentleman. All you can do to fuck it up at this point is act like a typical male and you will go home alone. Do I make myself clear?"

"And you say that I know how to take advantage of a situation," he replied. "Yes René, you are perfectly clear and I will be on my best behavior." The waiter brought our meal and Edouard ordered another round of Mimosas as we started to giggle like high school kids. "This is the best fun I've had in years," he said.

"You and me both," I replied. "And who would have thought that 2 days ago I was cursing my friends for abandoning me to the crowds on a subway platform."

"And I considered going back to my office to sleep on my couch. Who can understand fate?"

"Is that what this is, Edouard, fate? What about ships passing in the night, a quick beef and boff and then never speaking again? You are a man and this is the 21st century, you know."

"Even that could be fate but mixed with bad karma on someone's part I'll admit," he replied lightheartedly.

I laughed and said, "You're going to make disliking you very difficult if you keep this up. Please tell me why someone hasn't captured you by now? Bodies in the freezer or maybe something really bad?"

"Nothing like that. I seem to be looking for something or someone who doesn't exist. I find myself always searching but never satisfied with what I find. If I'm totally honest, and perhaps I shouldn't be this soon, but I felt something when I first spoke to you on the subway and it was special. I told you that I thought you looked nice even in the crush of humanity and you simply smiled and said 'thank you'. I would have expected a 'fuck you' or no comment at all, but you were gracious and polite. Do you have any idea how rare that is? Sorry, you live in New York so of course you do."

"Just as rare as a man asking a stranger if everything was okay and if he could do anything for her when she looked troubled," I said. "We notice and are touched by the same things; it is fate that we wound up talking to each other rather than staring into the dead eyes of other people on a subway after midnight."

"René, are there bodies in your freezer?" he said softly.

"Hopefully no more than you have in yours," I replied with a smile.

We finished our wonderful brunch and walked arm in arm onto the street a little before 3:30pm to get into our car for the ride back to Brooklyn. The Maître de made a point of shaking hands with Edouard and giving me a big smile and a faux kiss on my hand acknowledging my female persona and leaving me feeling like royalty. Edouard held my hand in the car and I rested my head on his shoulder, feeling very comfortable. As we pulled up in front of Edouard's apartment building I whispered teasingly, "This is not my building, you letch! What type of woman do you take me for?"

"We know the type of woman you are, Ms. René," came the response and we both laughed as we got out of the car.

"And you're sure this is the type of woman you want Edouard? There's no going back afterward you know," I said.

"I think so but there is only one way to find out for certain," came the quiet reply.

His apartment was clean, neat and nicely decorated, bright but not with sun flooding the windows. "Yes, this is you Edouard. I pictured your apartment this way in general and I imagine that you have extra toothbrushes in your gleaming bathroom with matching towels."

"You'll thank me for that later," he said as he pulled me close and kissed me on the lips. "I have been wanting to do that since Friday night."

"You read my mind," I responded before kissing him again and slipping my tongue gently between his lips.

As we separated I asked if I might remove my heels and jacket to get more comfortable unless he had other plans. He smiled and said that I could get as comfortable as I wished since his only plan was to have a nice afternoon with me.

I slowly removed my jacket, handed it to him and asked him to hang it up and then sat on the sofa to remove my shoes. Standing again I placed my hands on my hips with my legs slightly separated for effect and asked, "Do you like what you see? Your mouth is hanging open a bit so I will take that as a yes. Oh, and forgive me but I seem to have forgotten a bra in my haste to meet you earlier and I hope that my indiscreet attire is not a problem."

"It is a little distracting but I will try to adjust," he replied with a sly smile. "You look so sexy standing there and I mean that in the nicest way possible. I have seen you twice and both times you have taken my breath away."

I walked up to him and placed my arms around his neck and rubbed my breasts into his chest as I kissed him. "Sexy, huh? That's a nice compliment. Is that what you were thinking when you groped my butt on the subway platform Friday night?"

"René, do I look like a groper to you? You have hurt my feelings although I must admit that it is a tempting suggestion now that you brought it up," he said as he slid his hands down along my waist and rested them on my butt cheeks, giving a little squeeze in the process and pulling me close.

"It's getting warm in here so is there somewhere else we could go that's a little cooler? Maybe someplace I could lie down for a while?"

"I know the perfect spot," he said as he took my hand and led me to his bedroom.

"As I said before, Edouard there is no going back from here so proceed with caution. I don't want to be hurt for the sake of curiosity."

He turned me around to face him and gently began unbuttoning my blouse. After removing it, he placed his hands on the skin of my waist and said, "René, you seem comfortable with me and I know that I am comfortable with you. Let's not overthink the situation. I am not here to hurt you, and I honestly like you for who you are. Let's see where this takes us one day at a time."

I reached out to remove his polo shirt and undo his belt and watched as his slacks dropped to his feet where he removed them. Looking at him standing there in nice boxers with a bulge in the front and knee-high tan socks made me comment, "If your socks were black, you would look like an actor in a porn flick before the serious action started."

He undid my slacks and gently removed them, rolled my stockings down with expert technique, and placing his fingers in the waistband of my panties, slipped them down to expose my rock-hard erection. He looked into my eyes before kissing and licking the head of my dick, then he pushed me onto the bed and proceeded to remove his shorts and socks. When he was as naked as I was, he joined me on the bed where we kissed and held each other close feeling the excitement grow. Edouard kissed my neck and, as I lay on my back, worked his way down to my breasts, sucking and nibbling my nipples before continuing over my stomach to my abdomen before settling on my erect penis. Little by little he took it into his mouth and began to move up and down while advancing it down his throat until he had it all and my scrotum rested against his chin.

Holding my hips, Edouard increased the tempo of his movement until I was panting and begging him for release, something that he was unwilling to provide just yet. He whispered to me as he stopped his motion, "I'll bet you would love to cum right now, wouldn't you? Like to feel your semen pulsing into my hot waiting mouth. How badly do you want to cum?" he said but I refused to answer.

I grabbed the sides of his head and proceeded to fuck his mouth as hard and as deep as I could. I could hear him choking on my cock and the saliva that he was creating. I was bouncing my ass trying to fuck his mouth so I could get the release that I so desperately wanted, but he had tremendous control and held off.

Suddenly Edouard pushed his arm under one of my legs and in one swift motion managed to flip me onto my stomach and then pinned me down with his body. He held my wrists above my head and used his knees to spread my legs while I cursed him with every profanity I could manage. I bucked and struggled to no avail as I felt his erection inch its way into the crack of my ass searching for an entry point. "How badly do you want to cum now, bitch? Do you want to scream yet?" he said softly.

"Fuck you! You had better not stop this time, I'm ready to explode. Fuck me until I scream and don't stop until I tell you to."

He slowly pushed his stiff dick into my anus and I cried out as my sphincter stretched to accommodate the length and girth of his engorged cock. "You bastard!" I cried as he began to pump my ass in and out hitting all the sensitive areas in both directions. The pleasure that I was feeling flooded my body and I started to shake involuntarily as he brought me to the edge and then went over the top.

I bit into the mattress and released a muffled scream as I achieved orgasm, pulsing streams of hot semen under my stomach and Edouard's body stiffened as he ejaculated into my ass for what seemed like five minutes before lying still while my body held onto what was left of his shrinking erection. "So much for being a gentleman," I said with a laugh as I rolled over onto my back.

"You did say fuck you until you scream, I believe," he replied.

"Must you take everything literally?" I said as I leaned over and kissed him, and he pulled me close to his chest with an arm around my shoulder, a position that we stayed in for about 15 minutes.

"Can I interest you in a nap?" he said quietly.

"I was thinking the same thing but please promise to wake me gently," I replied.