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Guess We're Walking

By: Roustam



New York City can be unbearable in the summer. The temperatures rise to the 90s and above and the humidity levels keep pace with them. The towers of steel and glass reflect the sun's rays. Concrete and asphalt underfoot radiate heat. The subway stations are hotter than the streets. Conditions below ground are not helped by the masses of subway riders crammed together in close quarters. The smells that result from the heat and the crowding are repulsive, and they add to the general discomfort of making ones' way through the city.

I arrived in New York at 23. Fresh out of college, I took a low-level job at a major bank in midtown Manhattan. The pay was sufficient to allow me to rent a place of my own in Astoria, Queens. It was about 4 miles distant from the bank. I walked home from work quite often, taking a route that crossed the 59th Street Bridge. The bridge was great for pedestrians, with a wide walkway along the southern edge. The views of Manhattan were spectacular. I made a habit of carrying a camera with me and snapping a roll or two of shots when I reached the center of the bridge.

On many Saturdays I was asked to go to the office to help my superiors catch up on their backlog of paperwork. We all had a very demanding senior executive over us. He had no concept of life outside of work. I was paid overtime for the extra hours, so I didn't mind losing a day off every so often. I was also young and ambitious. It seemed to me that my devotion to the job might pay off in advancement sooner or later.

On one such Saturday, in July of 1990, I worked from eight in the morning until four pm. My task group got quite a bit done. We were glad to have everything in order for Monday morning. I packed my book bag and headed for home. As I left the air-conditioned lobby of the building I stepped into a steam bath. The thermometer must have read 100 or above and the humidity was atrocious. I immediately began to sweat. I walked half a block to the subway station at 53rd Street and Fifth Avenue. 

Every step of the descent to the lower platform seemed to raise the temperature several degrees. It was brutally hot. I couldn't wait for the train to arrive. Most of the train lines were air conditioned by that time. There were quite a few people on the platform already, but not nearly as many as on a typical weekday afternoon. I looked down the tunnel for any sign of an approaching train, but saw nothing. I walked over to one of the wooden benches along the wall and took a seat.

A young woman appeared at the bottom of the stairway and walked toward me. She was quite attractive, with jet black hair and a very slender body. She wore a black, tight-fitting t-shirt and tight, faded blue jeans. She had black sneakers on her feet. As she neared me, I could see that she wore no makeup, but she was pretty enough not to need it. She wore two silver hoop earrings. The young woman walked to the edge of the platform and checked for the headlights of the next train. 

I sat up and made room enough for her to sit next to me. I hoped that she would. Her butt was perfectly formed, if a bit skinny. I didn't mind; I liked skinny girls. I estimated her height to be 5'7", and her weight to be about 100 pounds. I was 6'3" and 195 pounds. Regular exercise and walking kept me in very good shape. I was told that I was handsome, but I considered myself average as far as looks went. I had no trouble finding dates, but at that time I was not involved with anyone. I hoped that that was about to change for the better.

The dark haired girl turned toward me and noticed the empty space on the bench. She looked at me and gave a little smile. 

'"I've been waiting a little bit," I said. "Nothing yet."

She sat down next to me and started fanning her face with a magazine she carried. "It better be here soon," she said. "I'm about to melt."

"That makes two of us," I said. "I hate this city in July."

We compared notes about the heat and the hassles of city life. She was funny and she smiled at our shared grievances against the weather and the Big Apple. I introduced myself and she told me her name was Gayle. We shook hands and shared a smile. It turned out that she lived in Astoria, also. Her apartment was much closer to the East River than mine, but not very far away from me. I was happy to hear that.

Thirty minutes passed as we waited and talked . Several dozen more subway riders made their way down to the platform. Tempers were beginning to flare among a few of them, as they always do when a train is late. Twice I walked to the edge of the platform to look for headlights. Nothing. After the third time I threw up my hands and shrugged at Gayle. "I don't know what to tell you," I said. "There must be a broken rail or something." Broken rails happened regularly, and stalled the trains for long periods.

"I can't stay down here," she said. "I think maybe I'll take a bus."

"Do you ever walk over the bridge?" I asked.

"No. Is it safe?" She seemed to consider the idea.

"Oh yeah," I said. "Especially in the afternoon. You just have to watch out for the idiots on bikes." I had nearly been knocked down on the bridge walkway before by bicyclists. "Would you like to give it a try?" 

Gayle thought for a moment, then grinned. "Sure," she said. "It might be fun."

"Great!" I said. "Let me just check one more time." I looked down the tunnel again, but this time I hoped that I would see nothing. I didn't. I shrugged again.

Gayle nodded, smiling, and said "Guess we're walking."

The still oppressive heat at street level was a relief after the much higher temperatures in the subway station. Gayle walked with me up Third Avenue to 59th Street, then over to the Manhattan end of the bridge walkway. I had sense enough to suggest that we get a couple of bottles of water for the trek across the bridge. It was nearly a mile across, and at times, if there was no wind, the walkway could get dangerously hot. We walked over to a deli and I purchased a large bottle of water for each of us. We took a long drink before we returned to the walkway.

It was a fairly steep grade up to the highest part of the walkway. It was easy for both of us, but we were, of course, bathed in sweat by the time we reached the halfway point. We talked the entire time. I learned that Gayle was from New Jersey, and that she had moved to Astoria the year before. She worked in a large bookstore near my office building. She said she put in all kinds of overtime to pay the rent and bills, but that she enjoyed the work and loved living so close to Manhattan. She said she was 21, single and not seeing anyone. I didn't ask her about her relationship status; she freely volunteered it to me. I took it as a suggestion of her availability. Before we moved on, I asked Gayle if I could take a photo of her against the background of the U.N. Building and the rest of the skyline. She agreed.

We then started the downhill walk to Long Island City. The heat was ungodly. The normal breezes I was used to feeling on the bridge were non-existent. By the time Gayle and I reached the ground in Queens we were ready for a break. I suggested that we stop in a great little Chinese restaurant nearby.

"Will they let us in like this?" Gayle asked, pulling at her soaked t-shirt.

"They don't care," I said. "As long as we order something."

We reached the restaurant in a few minutes. The cool air inside was a delight. We both drank several glasses of iced tea along with our meals. Gayle did not order much. That was no surprise, given how skinny she was, I followed her cue and just got some dumplings and an egg roll.

Our conversation covered every topic under the sun. Music. movies, food – all of the stuff that really matters in life. I was fascinated by her. She was at least as much a movie buff as me. It was always great to be able to talk to someone who immediately understood my cinema references. She asked as many questions as she answered, and I found myself profoundly attracted to her. When the meal was done, I paid the bill and we headed back out into the heat.

I offered to walk Gayle to her apartment building. She gladly accepted and pointed us in the right direction. She said that she rarely walked through this part of the neighborhood, as there had been some robberies there recently, and a couple of night time rapes. I didn't think it was that dangerous, but then I wasn't a hundred pound young woman, either. It felt good to be walking next to such a pretty girl in the city. I almost didn't mind the heat.

About fifteen minutes passed before we reached Gayle's apartment building. It was a brick, five-floor post-war structure that looked to be in very good shape. Gayle said that she lived on the ground floor. She fished her keys out of her pocket and walked over to the service entrance door. She stopped there and faced me. 

"Would you like to come in?" She asked. "I've got a/c and I think we both need it."

Would I! Of course, I said yes and followed her into the hallway of the first floor. It had gleaming tile floors and unmarked walls. We walked past a large laundry room that looked to be empty of patrons. Gayle's door was the next one we came to. Gayle smiled at me before she opened the door. "Please don't mind the mess," she said.

Gayle's apartment was a one-room studio with a tiny kitchenette in the back and a bathroom. It looked as though she had one closet. Two small windows in the kitchenette looked out onto the building's courtyard. Gayle had a twin bed along one wall and a small sofa on the facing wall. There were also two small upholstered chairs. She had an older, small TV in one corner, atop a stereo set. Milk crates holding VHS tapes and music cassettes stood next to the TV. She had a few plants here and there and a row of movie posters along the wall above the bed. I didn't see any "mess" to speak of; everything looked pretty orderly to me. There were some wrinkled clothes balled up in one of the chairs. That must have been the mess.

Gayle locked the door behind us and walked over to the air conditioner that took up half of one of the windows. "Make yourself comfortable," she said as she turned on the a/c. 

I sat in the empty chair and took in the room, and its resident. I was pretty excited at how the afternoon had gone. My plan that morning, as far as I had a plan, was to return home and eat a pizza alone. Now, in a gorgeous girl's apartment after a fantastic "first date," I hoped I'd be staying there for a while. Gayle opened her refrigerator door and took a brief look at the contents. 

"I can offer you a Diet Coke," she said to me. "I'm afraid that's all I've got."

"That's fine," I replied. "I like it."

Gayle took out two cans of soda and brought one to me. She sat on the sofa and held the can to her forehead. "That was a great walk," she said. "I can't believe I never did it, before."

"I like to do it for the photo opportunities," I said. "I've got a couple hundred pictures I've taken over the last few months. I have a great one of the sun setting between the Twin Towers. I'll have to show it to you." Hopefully in my apartment!

Gayle nodded. "I'd like that," she said. We were both quiet for a moment. Gayle spoke again: "Look, your clothes are saturated. I'd hate to send you home like that. Why don't you let me throw them into the washing machine and have them ready for you when you leave?"

I was at a loss for words! What would I wear? Not that I would mind sitting naked with her, but it was still fairly early in our friendship. 

Gayle noticed my anxiety and laughed. "I have a large robe in the bathroom you can use," she said. "In fact, why don't you take a shower while you're in there?"

Fantastic idea! This afternoon was really looking up, now. "Sure," I said, perhaps a little too enthusiastically. "If you're sure you don't mind, I'd really appreciate it."

"I wouldn't have offered if I didn't mean it," she replied. "Go ahead and strip off in the bathroom and toss the clothes out for me. I'm going to change in here, so don't come out until I tell you to." She stood up and I did as well.

The bathroom was tiny but neat and clean. The toilet sat almost beneath the sink which, in turn, nearly reached into the tub/shower combination. A small casement window high on the shower wall provided light and ventilation. I saw the robe hanging from a hook on the back of the door. As I stripped, I saw all of the beauty products that lined the edges of the sink and the tub. I always liked seeing the variety of products women seemed to require. In a moment or two I was naked and my wet clothes were wrapped up into a small bundle. I tossed it out int the main room. "I'll be in the shower," I said.

"Great," Gayle answered. "I'll get the laundry started."

I enjoyed a good, long, very hot shower. She had strong water pressure and plenty of hot water. I found a bar of soap that didn't smell like perfume and I went over every inch of my body with it. When I was done, I took a fresh towel from the two that hung from a rod and I dried myself. I donned the robe and opened the door slightly. "Can I come out?" I asked. There was no reply. I stepped back into the main room and saw that she was gone. I took my old seat, had a sip of the Coke and waited for Gayle.

A few minutes later, she returned. She wore a silk kimono-style robe and slippers. She gave me a big smile as she entered the room. "Did you enjoy the shower?" She asked.

"Oh yeah," I said. "It was exactly what I needed. I feel like a million bucks."

"Great!" She said. "I'm gonna take one too, then we can talk a little bit more. The clothes will take a couple of hours to finish."

I liked the prospect of hanging out, both of us in robes, for a couple of hours. Or more. Who knew where we might end up by nightfall?

Gayle showered and I relaxed in the chair. I heard her singing as she washed. It was music to my ears. I kept checking my robe to make sure that my dick wasn't making an obvious tent in it. I shifted my position a few times and folded the robe so as to disguise my excitement. I was as hard as a rock.

Gayle took her time in coming out. When she did, she looked lovely. Her hair looked as good wet as it did dry. She had tousled it a bit and it framed her face perfectly. She tied the robe as she walked to the sofa. She flopped down and crossed her bare legs. "Much better!" She said.

Definitely! Gayle's bare legs were very sexy. I liked the way she swung her small foot. She still had no makeup, nor did she need it. She sipped at her Coke and watched me. 

I must have been giving away my thoughts by my look. Gayle asked "What?" She chuckled a little.

I snapped out of my reverie. "What, what?" I said.

She laughed harder. "What are you thinking, Joe? It must be something good."

"Uh, just thinking about how good this day has turned out to be." It was the truth, just not all of it. I leaned forward. "Look, Gayle, I could not be happier right now. I am totally comfortable. Meeting you has been fantastic. I'd like to think we're on our first date."

Gayle smiled and nodded. "Me too."

I continued: "I think we ought to have at least one more. Date. I think we ought to pick a movie and then have dinner. How about this week, after work?"

Gayle pondered it, then her look turned blank, then anxious. I was taken aback, then nervous. I thought my offer was a sure thing. Gayle put both feet on the floor and crossed her arms over her stomach. She leaned forward and stared at the floor. Her voice quavered a little when she spoke.

"Joe, thanks. I'd love to do it. But there's something you have to know, and I hope you'll understand how hard it is for me to tell you." Gayle wouldn't look at me.

The possibilities flooded my mind. Boyfriend? Pregnant? Lesbian? Terminally ill? All of them? I had no idea. I cleared my throat. "Whatever it is, just tell me," I said. "I promise I won't get angry or anything. I like you a lot and I'd like to be your friend."

Gayle nodded, still looking at the floor. "You see...I was...I was born a boy...." She bit her lip.

What? I leaned back in the chair and felt as though the floor had dropped away. I stared at the ceiling.

Gayle spoke next. "I'm sorry. I truly am. I should have just told you right away. I was just...I was just having such a good time with you. You don't know hard it is to be transgendered. I have to watch everything I say and do..." She looked up at me. A tear had formed in each eye.

I struggled for the right words. "It's okay," I said, at last. "You did nothing wrong. Thank you for telling me." I looked to the side. "How long have you been living as a woman?"

Gayle wiped her eyes and cheeks. "A couple of years. I mean full-time. I knew from day one that I was a girl. There was no question in my mind. It was just that my parents wouldn't believe me when I told them. I was nine when I did and they just wouldn't have it."

"Is that why you moved here?" I said.

"Yeah. I went to college for a couple of years, but I really needed to be who I am. What I am. I couldn't do it at home." She relaxed a little and unfolded her arms. "Listen, I'll finish your clothes and you can be on your way. I had a great date and I –"

I cut her off. "No – I mean, if you'd like me to stay a little while longer I'd like to. It's up to you. I'd like to talk to you about it."

Gayle frowned and tried to suss out some hidden motive in my statement. "Are you serious?" She asked.

"I swear," I said, hand on heart. "I think I can understand how you feel. Or maybe how you think. I don't want to walk out on you just because you're honest. I respect that in my friends. The only difference between now and an hour ago is that I know a little bit more about you. And it doesn't make that much difference to me."

Gayle shook her head. "It makes ALL the difference, Joe. Have you ever dated a guy?"

"No," I said. "But you're not a guy."

Gayle rolled her eyes. "I have a penis, Joe. A dick. Balls. I have a woman's face and a man's equipment. Are you really going to tell me that that doesn't make a difference to you? C'mon..."

Now I was a little bit angry, but I kept my voice even. "Gayle, listen to me. So now I know what you have in your robe, between your legs. Big fucking deal. I look at you and I see a beautiful woman. You met me and you trusted me and we wound up liking each other a whole lot. Didn't we?"

Gayle's face softened a bit and she gave me a half-smile. "Yes," she said, barely above a whisper.

I continued: "Do you believe that I I'm not lying when I say that I'd like to see you again? I promise you it's not a problem."

Gayle studied my face. "Please don't lead me on," she said. " I've been beaten and I've been used and lied to. Guys get what they want and they're gone. I'm tired of it." 

I stood up and stepped over to the sofa. I sat down within inches of her. I took her right hand in my left. "Gayle," I said, evenly, "I promise you that I want to see you again. As much as you'd like. I want to do what every couple in this city does together. I had the best afternoon of my life with you, and I don't want for this to be the end of it. I have no plans to hurt you in any way."

Gayle turned into me and looked into my eyes. She reached up and placed her hand against my cheek. "You mean it, don't you?" She whispered. I nodded. She leaned her head toward me and gave me a light kiss on the lips.

I raised her hand with mine and kissed her knuckles. She watched me with what I took to be a mixture of relief and desire. I wanted to act on it. I patted my right thigh and said "C'mere."

Gayle stood and hesitated for a moment. "You're sure?" She asked.

I took hold of her waist with both hands and pulled her down onto my lap. She seemed weightless to me. She smelled very good. I loved the scent of her hair. My right arm encircled her shoulders and my left held her right hand. We kissed again. I felt her lean into my chest a little. She sighed. Our kisses became deeper and our tongues slipped around each other. We sucked on each others' tongues. Our eyes kept meeting and we both giggled quite a bit. My left hand slipped down to her leg and started sliding up toward her thigh. 


Guess We're Walking



Gayle stopped me and broke off the kiss. She gave me a serious look. "You're sure you're sure?" She asked. 

I answered by locking lips and continuing my caress up her leg. I found the edge of her robe and moved it aside, followed by the other. I then undid the loose sash around her waist. She alternately watched my actions and looked at my face. The robe fell open. I looked down. I saw a small, pale penis standing fully erect. It might have been four inches, at most, and not very thick. The pubic area was as smooth as silk. Gayle's scrotum was slightly darker, and equally small. My hand slid slowly upward until could cup her penis and balls in my palm. Gayle moved her legs apart slightly and moaned a little.

"Oh, that's so nice," she said as I encircled her shaft with my thumb and my index finger. We kissed some more as I began stroking her. She leaned forward a little and let the robe slide off of her shoulders. Her chest was as smooth as a baby's bottom, and she had two little mounds of flesh beneath her hard nipples. I freed her penis for a moment and caressed each mound. I gave the nipples a slight pinch. I could see that my attentions had the desired effect on Gayle. She laid herself back on the sofa pillows behind her. This move raised her pelvis a little, giving me all the access I needed to her penis. 

I took advantage of it. My right hand massaged her chest and stomach as I picked up stroking her shaft again. Gayle placed he left hand on top of my right and held the sofa with the other. She moaned and sighed as I stroked her. Picked up the pace a little. She pulled up my hand to her mouth and lightly bit the edge of it. I felt her penis twitch in my left hand. Gayle grunted and shot three streams of semen onto her belly. Her body tensed up for a moment, then completely relaxed. She let out a long exhalation.

"God, that was good!" She said. She rubbed her eyes and nose with her hand. "I needed that!" She added. Gayle sat up after a short rest and rewarded me with hot kisses. Then she stood up, revealing her entire body. It was an amazing sight. I was painfully aroused. Gayle dropped to her knees in front of me and untied my robe. She pulled apart the robe halves and exposed my nine-inch cock. I was lucky to have a good sized member that was wide, as well as long. It had reached it's full length and breadth long before this moment. 

Gayle took my shaft in both hands and started stroking it. She leaned in and took the head in her mouth. I rested my head against the back of the sofa and groaned. The tongue bath she gave me was heaven. She took as much of me into her mouth as she could manage. Gayle's tongue slithered and slurped and made noises that added to my pleasure. She really knew what she was doing. I took hold of her hair as my cock bucked in her mouth. An eruption of come shot, then flowed into her mouth. She made no attempt to back away or release herself from my grip. 

I thought that I was levitating above the sofa. It was that good. Gayle sucked the last drops out of me as I began to soften. She swallowed it all, and it had to have been quite a bit. That pleased me greatly. When she was done, I pulled her back up onto my lap. It was so nice to be naked and entwined with her. We kissed ferociously again. I rocked her in my arms. I wanted to throw her over my shoulder and carry her home with me.

"Mm – the clothes," she said. She moved off of me and picked up her robe. She slipped it on and stepped into her slippers. She winked at me and said "Don't go anywhere!"

I gestured to my naked body and exposed dick. "Like this?" I asked. We shared a laugh. Gayle scooped up some quarters from an end table and left the room.

I stood up and stretched. I felt so fucking good! I went to the bathroom to empty my bladder, then returned to the main room and finished my can of now-warm soda. I was hungry again, too. I remained standing as I waited for Gayle. It only took her a couple of minutes to switch the loads.

When Gayle returned to the apartment she started laughing at the sight of me, naked, standing in the middle of the room. "You really made yourself at home, didn't you?" She said, laughing. 

I beckoned for her to join me. She walked to me and turned around. I pulled her close and kissed her neck. She squirmed when I kissed her ear and licked the lobe. I just held her all the more tightly and continued the tongue tickling. My hands roamed all over the front of her. I slipped a hand beneath her robe and caressed her chest and stomach. Her sash fell away and the robe opened. I moved both hands toward her pelvic bones, then inward. I found her penis semi-hard. A few little brushes of it with my palms and it was fully hard.

"Turn around," I commanded. She obeyed. I dropped to my knees, kissing her chest, then the stomach, and then the skin around her privates. Her penis brushed my cheek. I gave it a little thought, and concluded that sucking her little penis was not really much different than eating pussy. I had done that for women several times and I enjoyed it. This pink appendage before me was just a slightly larger clitoris. I kissed the head and then licked the slit. I looked up to see her watching me. I gave her a big grin, then took the entire shaft into my mouth.

"Oh!" Gayle moaned. "So good..."

I started a good sucking and licking routine all over her penis. Every bit of it got a kiss or a licking, or both. It twitched in my mouth. Gayle put her hands on the sides of my head and thrust herself into me. The pace picked up. We manage to match our movements just right. Gayle let out another groan and shot a few streams of thin come into my mouth. I gagged a little at first. I did manage to keep all of it in my mouth. I swallowed. The taste is hard to describe, but it wasn't unpleasant. I thought: "I could get used to this." When I was sure that Gayle was done, I stood up and kissed her. She devoured me! We fell back onto my chair. She thanked me with kisses and mumbled words.

My cock was now stirring again. Gayle felt it and giggled.

"Doesn't take long, eh?" She said.

"Nope." I replied. "And he knows what he wants, too, baby." I said. "Why don't you hop up and let that robe down?"

Gayle stood and slipped off the robe. I gave my cock a couple of tugs to restore it to full hardness. Gayle went to the bed stand and retrieved a small bottle of lube from the drawer. She crouched in front of me and poured some lube onto her hand. Then she smoothed it all over my shaft and cock head. When that was done, Gayle put the bottle on the floor and turned away from me. She slowly lowered herself toward me, placing her hands on the arms of the chairs. In a few moments her asshole was poised just a millimeter from my dick head.

And then I was inside her. Gayle didn't hesitate for a second. She did gasp and tighten fiercely around my shaft, but she slid down until her buttocks rested on my thighs. "Oh FUCK!" She shouted. I wanted to yell, too! Gayle took a second to acclimate herself to the intrusion. She started rising until just the head remained inside. Then she lowered herself again.

What followed was probably the greatest single experience of my life. Gayle picked up the pace and kept a running commentary of moans and grunts and profanity. She was a wild thing! I couldn't help but grunt and groan and issue a few four letter words of my own. I can't do the pleasure I felt justice in words. Trust me: it was more than intense. When I came, it was stronger than the last ejaculation. I felt my fluid coat her insides and surround my cock. Gayle fell back on me. I touched her dick and she came again. Her interior muscles squeezed the hell out of me. We both gasped for air.

My cock slowly removed itself from Gayle's ass. She curled up on me and snuggled. I could have spent all night in that position with her. Our embrace only ended when she realized that the laundry was done.

It was, to paraphrase Bogie, the start of a beautiful relationship. Within a week, Gayle was staying with me at my place on the weekends. By the end of the month, she agreed to move in with me (my place was much larger), but she kept her apartment with a view to turning into an artist's studio. I was happy to help her out with the rent.

I did make my way up the corporate ladder. Extra responsibility was rewarded with much greater pay and the prospect of a vice president's position someday. Gayle benefited from my success – she was able to focus on painting and sculpting full-time in her new studio. We moved to a larger apartment in Astoria and considered buying a house in the Catskills. 

Gayle decided, after much discussion, to keep her penis and testicles intact. To be honest, I enjoyed playing with them. She was not entirely convinced that she would get as much pleasure after a sex change as she did with male parts. I had no trouble with that decision. Gayle did stay on a hormone regimen. When she turned twenty-five, I surprised her with a paid-for breast enlargement operation. It wasn't drastic; just enough to giver her the very realistic pair she told me she always wanted. 

Our sexual relationship has remained as intense and fulfilling as ever. We are completely monogamous and I've never given any thought to going back to women. I HAVE a woman! A gorgeous, intelligent, supportive woman who would kill for me. The fact that a few inches of flesh protrude from her doesn't make a bit of difference to me. I'd kill for her, too.