9 comments/ 45374 views/ 33 favorites A New York City Romance By: Dani-Amande CHAPTER ONE Friday afternoon, I finished my last class, grabbed my backpack, and ran for the bus. It pulled up as I reached the stop. "Return ticket to the city," I said, paid, and took a seat near the back of the bus. Two hours later the bus was heading under the Lincoln Tunnel. The first view of the New York skyline was always a thrill, and as the road pitched up and we exited the tunnel, I had the sensation of my life opening up again. Not that this was going to be such an exciting evening, but, hey, it was surely better than another night at home in far western New Jersey. I was in the city for my big sister's twenty-fifth birthday party. Her friends had hired a club downtown for the party, and although they were all very nice, they were mostly medical students and doctors. Maybe I'm misremembering, but Sharon seemed to have been more fun before she went to medical school. Still, looking at it from society's perspective, I suppose it's a good thing that doctors aren't so wild and crazy. I was going to stay with Susie, Sharon's best friend from high school. Susie wasn't going to be a doctor. Nor a lawyer, nor an MBA, nor anything mainstream. She taught dance at a school in Manhattan and wrote funny novels about dance and sex. She lived in an apartment on the west side with a couch for a guest to sleep on. I loved her apartment, but that's because I loved her. Susie and I had a history. She was the first girl to touch my cock, and hers was the first pussy I had licked. That's all we had done. Anything more would be inappropriate, she said, because she was my sister's best friend and so much older than me. "Only six years!" I would always protest. "Yes, and that means you're still a baby," she would respond. But I didn't mind too much because she could do amazing things with her fingers and I loved running my tongue slowly along the length of her pussy and hearing her moan. But ours was a secret history. Not even my sister -- especially not my sister! -- knew about us. And since Susie had moved to the city I didn't see her so often, even though we texted and emailed almost every day. I was closer to her than Sharon. I would never have asked Sharon for advice about girls, but Susie was always full of wisdom and commentary. It was getting dark as I walked from the bus station to her apartment. She opened the door, and kissed me on the cheek as I walked in. "How are you, sweetie?" she asked. "Good," I said, looking around her neat and tidy apartment. "So are you ready to party?" she asked. I rolled my eyes. "Yes, I know what you mean," she said. "Still, we're going for Sharon, so we've got to pretend that we're having the time of our lives. And maybe you can meet a cute medical student," she added. "Are there such things?" I asked. "I met one once," she said. "Sharon set me up with him. He was cute. Boring but cute. I used to fuck him just to get him to shut up about medical school." "That I doubt," I said. "Ok, you know me too well. I fucked him because he had a great body and a beautiful cock. How about that?" "Sounds more likely," I said, returning her smile. "I figured we'd head down to the party at about nine," she said. "Ant later and they'll all be heading home. So let's have a drink and then we can change into our party clothes." Uh oh! I thought. Susie saw the look on my face. "Is there a problem, baby boy?" she asked. "I forgot my bag," I said. She looked at the bag I had dropped on the couch. She pointed at it. "It's there." "No, the one with my clothes. I left it in the locker at college and forgot it in my rush for the bus." "Problemo," she said, looking at my rumpled t-shirt and worn jeans. "Sharon will be mightily pissed if you turn up like that." I shrugged my shoulders. "So what can I do?" "Don't know," she said. "Let's have a drink. I'm more creative when I've had a drink." She poured two glasses of white wine and we sat at each end of the couch facing each other. "Do you have any of your boyfriends' clothes around?" "No. Nothing suitable for a party at a club, anyway." I was getting desperate, imagining my sister's anger. "How about you then. Do you have any slacks or pants that I could wear?" She laughed. "Have you ever seen me in slacks?" She pronounced the word as though it described something obscene. "All I have are jeans and workout clothes. How about some dance tights? That's it! Go as a dancer and tell Sharon you thought it was a fancy dress party." "You're not helping," I said glumly. Susie took another mouthful of wine. "So how about this then? If you want to borrow my clothes, let me dress you up like I used to. Some makeup, a cute white blouse and a short skirt, you'll be a sensation." I haven't mentioned our dress up games. Maybe it's because Susie didn't have any sisters of her own, but there was a time when the only game she wanted to play with me was dressing me up. I didn't mind because what came before dressing up was undressing, and there was little I liked more than being naked in front of her, and our games usually ended with her hand on my cock and my mouth on her pussy. It didn't much matter to me that while that was happening I was wearing dress and girl's underwear and had my face and hair made up, and that she called me Stephanie rather than Stefan. "No," I said. "I'm not going to Sharon's party as Stephanie." "But Stephanie is so pretty. You'll have so much fun." The fact is that she did make me look very pretty. I used to marvel at how she transformed me from a teenage boy to an attractive girl. But even so, it wasn't going to happen tonight. We sat on the couch looking at each other, not speaking. Susie poured some more wine for us, and we continued sitting silently. "Please," she said. "No," I replied. "Please," she repeated. "No." "But please!" she said, drawing out the pleeaase to a long thin whine. This is always how it went. Susie got an idea in her head and would ask and ask and ask until she wore me down. "Why not," she asked. "Because my sister will hate me," I said. "But I'll explain," she said. "She'll blame it on me. And you'll look so cute, she'll be surprised and not angry." "No." "But it'll be so much fun?" "Everyone will think I'm crazy." "But they're medical students! They'll love that! You'll be the star of the party." "No." "Ok, then. I'll suck your cock if you do it." That made a difference, very definitely. I wasn't a total innocent, but if truth be told I hadn't had many girlfriends, and my success rate at persuading them to touch my cock was pretty low. And none had accepted my invitation to suck it. Susie noticed the change in my expression. "So, baby boy, how about it? Your cock sucked for the very first time and I dress you for the party. Do we have a deal?" "You'll tell everyone that me dressing up was your idea?" "Yes." "And that I didn't want to do it, but had no other option?" "Yes." "And that you got me a little drunk before I agreed?" "Totally plastered, if you want." "Ok," I said. "Ok, what?" she asked. "Ok, we've got a deal. You dress me up and you'll suck my cock." "Deal," she said. "Now get naked." That's the bit I liked of course. I kicked off my sneakers, pulled my t-shirt over my head, and undid my belt and let my pants fall to my feet. Susie sat on the couch looking at me. "Baby boy, you have such a lovely body," she said. She leaned forward and cupped her hand around my balls, and my cock stirred in response. "And I love your cock. It's so pretty, so cute, so delicate." She took my cock in her other hand, and gently pulled me towards her. She leaned forward and took my cock in her mouth. It hardened as she sucked it, gently caressing it with her tongue. Her hand stroked my shaft, masturbating me as she sucked. My eyes closed with the intensity of the pleasure. So this was what it was like to have my cock sucked. It was heaven. Beyond heaven. I was lost to her touch. I imagined her mouth drawing up my cum from deep inside me, coaxing it into my cock, slowly raising it until it was ready to spurt out through her lips into her mouth. I wanted so much to fill her mouth, to show her how much cum I could produce for her as though that were a measure of my gratitude. I came, shooting hard into Susie's mouth. She sucked me gently and stroked my shaft as the tension in my body relaxed. Then she drew me down on top of her on the couch, and she held me close to her, my head cradled in her shoulder, and she stroked my hair, and kissed me softly. "Was that as good as you imagined, baby?" she asked. "Yes," I said. "It was incredible. It was so intense." "I'm so glad I was the first to do it you, my baby brother." "Me too. I'm so happy it was you." We lay together for a long time, me so happy and content in her arms. Then, after long minutes, she asked softly, "Are you ready for me to dress you?" "You can do anything you want to me." She kissed me again, and stood up. She pulled me to my feet. "Come. Into my bedroom, little boy." After the job Susie's mouth did on my cock, and after the couple of glasses of wine, I was no longer very concerned about Sharon's party. So what if I turned up as Stephanie? So what if Sharon is angry? So what if everyone there thinks I'm weird? I can live with all that because Susie just sucked my cock! She stood looking at her closet. "So what might my little Stephanie wear tonight?" she asked. "Nothing too slutty," I said, remembering some of the outfits she had dressed me in before. "What's wrong with slutty?" she asked. "You've just had your cock sucked by your surrogate older sister. Don't you feel a little bit slutty?" "Maybe. But only a little bit," I said. "Maybe you should suck me some more to make me feel more slutty." "Good try, baby brother, but the deal was one time only." "But it was sooo good," I pleaded. "Yes, and that's why I can now dress you as I want. Lie on the bed." I lay down. Susie took some white cotton panties from her closet and placed them over my cock. Then a black leather miniskirt, and placed that over my legs as though I were wearing it. Then she placed a white camisole and a white silk blouse over my chest. "That's pretty," she said. "Classic, but the leather gives a hint of sluttiness. Sit up," she instructed. I sat on the edge of the bed and Susie made up my face. She was truly an artist with makeup. After a few minutes she took a step back and looked at me. "That looks right," she said, and took my hand and led me to the mirror. The effect was remarkable. She had swept my long blond hair back over my ears and held it back with a clasp. She had applied eye liner and mascara so that my eyes became the prominent feature of my face. She had applied blush to my cheeks, and a subtle pink to my lips. I looked like a girl made up for her prom. "That is amazing," I said. "Ok. Try on the clothes," she said. I pulled on Susie's panties. "They fit ok," she said, "but you can't have this sticking out." She tucked my cock into the panties. "Now the skirt," she said. It was tight, but I could get it over my hips. She stepped back and looked at me. "I don't know," she said. "It's very cute, but it's quite revealing. If you get hard, it will be obvious to everyone." "They're medical students," I said. "How hard am I likely to get?" "Good point," she replied. "But if for any odd reason you start getting hard, sit down quickly." Then the camisole and the blouse. "So how many buttons do we leave undone?" she asked? "Too many, and it's apparent you don't have any boobs. Too few, and it looks as though you're frigid." "Let's do frigid," I said, and she buttoned all but one of them. "So my dearest Stephanie, we're done," she said, leading me to the mirror again. I stood there entranced. The skirt reached half way down my thighs and the blouse pulled tightly around my slim waist. Susie stood behind me. "And the best of all," she said, "is this." She touched my ass. I turned my head around to see the reflection of my ass in the mirror. The leather enfolded it tightly, accentuating its curve. "No-one seeing that ass will have any doubts that you're a girl," she said. "Now get out," Susie said. "I have to change." "But I want to watch," I pleaded. "And get hard? And start dribbling cum in your panties and down your legs? No. Out." "You're no fun," I said. "That's not what you said when I was sucking your cock," she replied. "Well, ok, but it's not fair to suck a boy's cock then deny him the pleasure of seeing you undress." "Out!" I left. Susie came out a few minutes later in a short white close-fitting dress. "What do you think?" she asked. "Amazing," I said, and I meant it. Susie was beautiful, and the dress accentuated her delicious body. "Shoes," she said. "I've forgotten shoes." She went back into her bedroom and came out with some sandals. "Not perfect," she said, handing them to me, "but all my other shoes will be too small." I put them on, and they felt comfortable enough, and we went down to the street to flag a cab. CHAPTER TWO Standing on the curb waiting for a cab felt like one of those dreams where you're walking down the street naked. I felt the cool breeze on my bare legs, and I imagined that everyone was looking at me, knowing I was really a boy. Susie sensed my anxiety, and put her arm through mine. "You look so feminine, sweetie. No-one could guess that you've got a pretty little cock under that skirt." She laughed as my skirt lifted up when I sat down in the back of the cab. "Two things to remember," she said. "First, when you sit down, smooth your skirt over your ass so it doesn't hike up like that. Second, keep your knees together when you sit." I closed my legs. When the cab arrived at the club, I copied how Susie exited. Back on the street, I breathed deeply, anticipating my sister's explosion at seeing me. "Why don't I go in and explain it to her first?" Susie said. "What, and leave me alone on the street?" I asked, looking around nervously. So we went in together. It was dark inside, and the music was loud, and no-one paid any attention to me as we walked in. A few friends greeted Susie, but even people I knew didn't seem to notice me. Susie pointed to where Sharon was dancing with her boyfriend. "Wait here," she said. She walked over to Sharon, and kissed her cheek in greeting, then spoke something in her ear. I could see Sharon turn to Susie with an incredulous expression and her mouth form a loud "What!" in Susie's ear. Susie said some more, then pointed in my direction. Sharon looked to where I was standing and Susie took her arm to lead her to me. Sharon stood looking at me with an odd expression on her face, anger mixed with bemusement. "Stefan?" she asked. I nodded, unable to meet her eyes. "I'm sorry," I murmured, I forgot my . . ." My voice trailed off in my embarrassment. "You look so beautiful!" she said, her expression softening. "I wouldn't have recognized you at all." She leaned forward and kissed my cheek. "It's just as if I have a little sister. How wonderful!" She took my hand. "Come and see my friends. They'll be amazed." She led me to the table where she had been sitting with some of her friends. I recognized most of them as I walked up to the table. We stood by the table: Sharon, Susie and me. "I want you to meet my little sister, Stephanie," she announced. They all looked at me, surprised. "Your sister?" one asked. "When did you get a sister?" "Just recently," Sharon said. "Isn't she cute?" Then one of her friends cottoned on. "Stefan!" she said. "That's Stefan!" Sharon nodded. I blushed. "That's amazing," her friend said. "He does look like your sister." "You can thank Susie for that," Sharon said. "He forgot his party clothes and Susie dressed him up as my sister." Her friends seemed to accept that as a reasonable explanation of why I was dressed as a girl, or perhaps were too polite to ask more. Either way I didn't much mind. I sat down at the table next to Susie with a sigh of relief. A steady stream of Sharon's friends came over to the table to wish her a happy birthday. One of them noticed Susie at the table, and she stood up to kiss him as a greeting. He was tall and slim, and even in the semi-darkness I could see he was good-looking. Susie turned towards me. "Daniel," she said, "this is Stephanie, Sharon's little sister." "Hi Daniel," I said quietly. "Hi Stephanie," he said. "I didn't know that Sharon had a sister." "Stephanie doesn't come into the city very often," Susie said. "I'm glad you decided to come in for the party, then," he said. Then he added, somewhat hesitantly, "perhaps you'd like to dance?" I must have seemed half-witted because I felt my face became quite blank. But Susie and the others were keen that I accept. "Yes, Stephanie. Go dance," Susie said to general agreement. I managed to pull myself together as far as to shake my head, and my mouth managed to form the word "no," even though no sound came out. "Yes, go on," someone said. "She's very shy," Susie said to Daniel to explain my reluctance. "Come on Stephanie," she said to me, taking my hand and pulling me up from my chair. "It'll be fun." I should have resisted and tried to explain the joke to Daniel, but rather than embarrass him, I let her pull me up. I stood next to Daniel, at a loss as to what I was to do next. "Go on, go dance," Susie said, patting me gently on the ass to move me towards the dance floor. I followed Daniel, hearing the enthusiastic cheers from the table behind. We started dancing. At least, that's what I was pretending to do. I had no idea how to dance like a girl. Daniel must have regretted asking me, for I was moving like I was being jerked by puppet strings, with an expression of panic on my face, quite unable to look him in the face. I could sense that the cheers from the table had turned into laughs. And that made me angry. Not for myself, but for Daniel. He seemed like a nice guy, and I didn't want the joke to go any further than it had to. Maybe I can get away with it, I thought. Have this dance, then thank him, and go sit down, and he would never know that I wasn't what he thought I was. My plan, as desperate as it was, made me relax a little, and my movements became less uncoordinated. I moved away from the table, into the crowd of dancers, so we couldn't be seen. I looked around to see how other girls were dancing, and tried to mimic them. And I even managed to catch Daniel's eye and return his smile. He leaned forward so I could hear him. "You dance so well," he said. I laughed, half wanting to reply "You can't have danced with many girls, then," but thought better of it. So we continued dancing, and as we did I felt the tension leaving, and started enjoying it. It wasn't so hard dancing like a girl, after all, as the difference mainly seemed to come down to a lot more movement of chest and ass. In fact, it was kind of fun, I thought. Maybe this is how boys would move if they weren't so uptight, rather than shuffling from one foot to the other as though they were treading water. And the movement of my clothes against my skin with these more expansive moves was also fun, and I found myself experimenting with how far I could move without my skirt lifting up so far that I would show off my ass. The excitement of my dancing radiated through me as though emanating from the dance floor, up my bare legs, through my groin, to my chest and arms. I should have stopped then, but, no, I thought, let me play this out more. This was new a new and different thrill. This was the adventure I came to the city to find. My cock started to stir and my ass and groin became a bigger part of my dance. As I moved, my cock rubbed against the fabric of the panties and against the leather of the skirt, the leather caressing it and making it grow. It felt so wonderful. I wanted the dance to continue, the music to get louder and the dancing more frenzied until my excitement grew and grew until it reached its climax. A New York City Romance But then music suddenly stopped and the lights came up a little, and one of Sharon's friends appeared on the stage to lead a round of singing Happy Birthday. I froze, fearing to look down to my skirt to see how I was giving myself away. Daniel took a step towards me, and I could see his lips starting to say "Thank you for . . .," and I feared that he would step too close, that he would brush up against me and would feel my hard cock against his leg, and the embarrassment that would follow. So I panicked. As he stepped forward, I stepped back, and then turned and rushed away off the dance floor to a dark corner where I could sit down and hide until my erection had subsided and I could sneak back to the table where I had been sitting with Susie. The singing ended and the lights went down again. I went back to the table and sat down next to Susie. "I saw you dancing, sweetie," she said. "You looked like you were having fun." "No," I said. "Ok, yes. But that was a nasty trick to play on Daniel." "You're right," she said. "It was thoughtless. But he didn't mind, did he?" "He still doesn't know!" I said. "So that's ok, isn't it?" she said. "He won't realize that he was deceived by your girlish charms." "Maybe not," I thought, thinking of how quickly he would have been disabused if he had seen what was distorting my skirt. I told Susie what had happened. She kissed me on the cheek. "So it was worth dressing up just to feel that sensation?" she asked me. "So you forgive me for making you dress up?" "Yes," I admitted. "I've never enjoyed dancing so much." CHAPTER THREE The next day I took the midmorning bus back to New Jersey. I texted Susie when I got home. "Thanks for a fun evening. And thanks for making me look so pretty! Love you." "Love you too, baby brother," she answered. "When do we get to play dress up again?" "Whenever you want to suck my cock again," I answered. I got another text from her Monday as I was heading to lunch. "Daniel knows," she said. "How?" I replied. "A friend of Sharon's told him." "Is he mad?" "Dunno," she replied. I thought about it over lunch. The more I thought about it the more upset I was. I should have stopped the joke straightaway. It was as much my fault as theirs. I texted Susie: "How can I reach him? I want to apologize." She gave me his email. I sat there composing an apology. "Dear Daniel," I wrote, then deleted the "Dear." "I want to say sorry for Saturday night. The joke went too far and I should have put a stop to it before we started dancing. I should have realized that the longer it went on the worse it would be, but I didn't have the courage to confess to you what I really was. I'm really very sorry about what I did, and feel like such an idiot. I hope you will forgive me." I read it over and changed the word "what" to "who," and sent it. I got a reply that night. "I'm not at all upset. I'm amazed, though. I didn't for a moment imagine that you weren't Sharon's sister. You looked so pretty and when I was told who you were, I couldn't believe it at first. And it was such fun dancing with you. You dance so well. So don't feel bad about it, because I don't." "Susie is incredible with make-up," I replied. "And I also had fun dancing. Maybe feeling half-naked on the dance floor released some of my inhibitions!" "That skirt was short, wasn't it?" he replied. "But you have great legs, so you can carry it off." I sent the email chain to Susie. "What a nice guy," I wrote. "Great legs!" she replied. "You don't think I have great legs?" "You have beautiful legs, sweetie. But Daniel sounded as though he was writing to Stephanie, not Stefan." "I guess we're easily confused," I replied. The next couple of days I buckled down to work. Thursday morning, however, I had my usual pre-weekend blues. I had nothing planned for the weekend, and all my buddies would be with their girlfriends, and I didn't have a girlfriend, so I wasn't going to do anything. And in the back of my mind I was contrasting it with the excitement of the previous weekend. Oh well, I thought, maybe I'll just fall asleep in front of the tv again. That will be painless enough. But Thursday afternoon I got an email from Daniel. "What are you doing Saturday night? Would you like to go dancing with me?" I read the message over and over. Had I read it right? "You mean as Stephanie?" I replied. "Yes. She's such a great dancer," he wrote. "I don't know," I answered. "Let me think about it." "Of course," he replied. "HELP!" I begged Susie as I sent her the emails. "What shall I do?!" She called me a couple of minutes later. "So my little Stephanie has got herself a date for the weekend," she said, laughing. "With a handsome doctor, what's more." "You think he's asking me on a date?" I said. "Sweetie, don't be silly. You're a great dancer, but I doubt that's why he's asking you out." "So what do I do? Tell me," I said. "Say no," she said. I paused. "Really? You think I should say no?" "Yes," she said. "You don't really want to come all the way into the city and have me dress you up again just to go and flaunt your great legs and cute ass on a dance floor, do you? And you'll probably just end up getting hard again and I'll have to get my skirt cleaned, and that will be expensive." "I'll pay for that," I said, then quickly regretted it. "Aha!" Susie said, doing her best Clarence Darrow impersonation. "Why do I suspect that you don't really want to say no?" "So I have a boring weekend ahead of me at home. There's nothing wrong with going dancing." "Nothing at all, sweetie." "So should I?" I asked. "What do you want to do? Only you can decide that." "I know, I know," I said. "I do want to go. He's a nice guy, and I loved dressing up and going dancing last weekend. But to do it again . . ." My voice trailed off. "Makes it seem like you might enjoy it too much?" Susie asked. "Yes," I admitted. "Doing it once was a lark. Doing it again will make me . . . I don't know what it will make me." "So go and find out. Find out what it makes you." "But what if he wants to do more than dance?" I asked. "Depends if you want to do more than dance," she said. "I don't," I said. "Then you won't," Susie replied. "He's hardly going to force you to do anything. Imagine the headlines: 'Doctor molests boy dressed as girl in nightclub. 'I was overcome by her great dancing,'" he confesses." "You're right," I said. "I'm being an idiot." "So you're going to go?" she asked. "Only if you can dress me," I said. "Hurray!" she relied. "And this time with added sluttiness." "No sluttiness!" I said. "He's a doctor. I don't want to scare him." "See you Saturday, baby bro," Susie said. "Yes," I said. "And thanks Susie. I love you." I went back to my email. "Yes, I would like to go dancing with you Saturday night," I wrote. Then added at the end, "Stephanie," and sent it to Daniel. CHAPTER FOUR When I arrived at Susie's apartment Saturday evening, she led me straight to her bedroom. "We have to be quick," she said. "Believe it or not, I have a date too. So get naked, baby." She undressed too, then sat back on the edge of the bed and spread her legs. She motioned for me to kneel in front of her, and when I did she pulled my head between her legs. I buried my face in her pussy and listened to her moans as I sucked and licked her swollen lips and clitoris. She came quickly and loudly, thrusting her pussy hard against my face. "Wow," she said. "I needed that. I've been horny all day." "Me too," I said. "Thinking about me, or your date?" she asked. "You, of course," I replied. "Of course, sweetie," she replied, and pulled me up onto the bed next to her and started to stroke my cock. "But haven't you thought at all about Daniel undressing you?" she asked. Before I could protest that I hadn't, she kissed me deeply, and her hand held my cock more firmly. "Because I would love to how excited he gets when he sees Stephanie's cute little cock," she said. Her kisses and her hand on my cock had me so close to cumming. "And it would be such a turn on to see his mouth on her cock and the excitement on her pretty face," she said. She moved down on the bed and took my cock in her mouth. I came as soon as her tongue touched me, my back bracing on the bed as my orgasm flooded over me. Susie kissed me. "Ok," she said, "we girls really do have to hurry if we're going to be ready for our dates." She put on my make up, and dressed me. "The skirt is very short," she said, "and very light. It's great for dancing." She was right: it was very short, and unlike the heavy leather of the skirt I wore last week, the light cotton felt like nothing against my thighs. "How does that feel?" she asked. "Like I'm not wearing anything," I said. "Yes. Isn't it great?" she said. Daniel texted me a few minutes later. "Just getting out of work. Going home to change and I'll be there in about twenty minutes." Susie answered the door when he arrived. "Take good care of her," she said to Daniel as we left. I looked at him and rolled my eyes, and he smiled. Daniel suggested that we go for a drink before we went dancing, so we took a cab to a small, dimly-lit bar in Soho and sat in the corner. The drink relaxed my nerves, and we were soon chatting as though we had known each other for a long time. After a a while I had almost forgotten that I was dressed up, but each time I looked away from Daniel I thought I caught someone looking at me wondering what I was. After a second drink, Daniel asked me if I was ready to go dancing. "You bet," I said. We took another cab. After a few minutes the cab pulled up in front of a seedy-looking building. Over the door was a small neon sign flashing just one word: "GIRL." There were a few people on the street in front of the entrance, and I felt their stares as we walked to the door. "You've been here before?" I asked him, a little too nervously. "No," he said. He too seemed nervous. But once through the door, the noise and heat spilled over me and washed away my nerves. I took Daniel's hand and led him to the dance floor. The energy of the music made me forget the seediness. I craved the same excitement I felt dancing with him last week. As I danced, the soft fabric of my skirt exposed more and more of my legs as my movements became more and more confident, and I felt even more naked then I had last time. When my eyes got used to the dark, I began to see some of the other dancers, and it slowly dawned on me that I wasn't the only boy dressed up for the evening. Daniel saw me looking around, and smiled at me. He leaned towards me. "Checking out the other girls?" he asked. "They're so pretty!" I replied. "And so are you," he said, and although I laughed at his compliment, I was glad he had made it. We danced and danced. The same thrill as before ran though my body, and my cock began to grow. This time I didn't attempt to stop it. Soon my erection pressing against my skirt was obvious to anyone who wanted to look, and I didn't care who saw how excited I was. I caught the eyes of girls looking at me, and we returned smiles. And I wanted Daniel to look at me and see my excitement, but his eyes remained on my face, and he kept a respectable distance away from me as we danced. I don't know what time we left the club. I walked out to the street as though coming out of a trance. The cool air brought me back to real life. Even at that hour there were still people on the street, and my exuberance and excitement quickly vanished. We walked down the block silently. "Why so quiet?" Daniel asked. "I get the impression that everyone's looking at me wondering what I am," I said. Daniel laughed. "They're looking at you because you're so cute," he said. He stopped next to me and pointed to our reflections in the window of a clothes store. "See," he said. "Very cute." He was right. Susie's transformation still worked. "And you'd be even cuter in this," Daniel said, pointing to an outfit in the store window. I looked at the mannequin's high leather boots, very short red skirt, and big red cape. "Your Little Red Riding Hood fantasy?" I asked. "You see me as the big bad wolf?" he asked. "Maybe I should try it on and see the effect it has on you," I replied. "How about that dress?" he asked, pointing at a mannequin wearing a low-cut short black dress. "I don't have the boobs," I replied. "You're right," he said. "But I guess that didn't stop some of the girls in the club," I said. "They were probably false," Daniel said. "They looked real enough," I replied. "Or implants, perhaps," he said. "So maybe I should get some implants then try on that dress," I replied. "What size?" he asked. "I don't know. What's your preference in boobs?" "Not big," he replied. "I'm so slim," I said. "Large boobs would look funny, I think," "They have software that allows you to see what they'll look like. You press a button and you can grow your boobs on the screen." "How do you know these things?" I asked. "I'm a doctor. Trust me." "I bet you say that to all the girls," I replied, and kissed him lightly on the cheek. I put my arm through his and we walked on to the corner. "Let's take a cab," he said. "I can walk further," I said. "No, I should get you home," he replied. Daniel was silent for the cab ride. When we arrived at Susie's apartment, he held the cab door open for me and helped me out. "That was so much fun," I said. "Thanks for taking me out." "It was fun," he said, not sounding very convincing. "Sleep well." Then he got back into the cab, and I walked up to Susie's apartment. "Oh well," I thought, regretting my kiss. "That's the last I'll see of him." CHAPTER FIVE I took an early bus back to New Jersey. Susie called me later in the day. "So how did it go?" I told her all about the club, the dancing, our walk, and how Daniel had come over silent after I kissed him. "You kissed him!" Susie exclaimed. "On the cheek. Very lightly. It was nothing," I said. "It sounds very romantic," she said. "Obviously he didn't think so," I replied. "Maybe after all he just liked you for your dancing." "Maybe. Or maybe he just doesn't like girls." "I'm sorry, sweetie," she said. "But he might still call you." "Maybe," I said, but I wasn't going to hold my breath. The week dragged by. Each time my phone made it's 'you've-got-a- message' trill I hoped it was Daniel. But he didn't write. By Friday I had given up hoping and was starting to contemplate the weekend with my usual dread. Why had I kissed him? I asked myself. I hadn't planned to; it just happened. I spent the weekend in my bedroom with the curtains drawn to shut out the outside world where everyone but me was having fun. Susie called Sunday evening. "You still alive?" she asked. "Barely," I said. "You're moping," she said. "Moping?" I replied. "That's what teenage girls do. I'm depressed. That's different." "About Daniel?" "No, not about Daniel. About how boring my life is." "Without Daniel to dress up for?" "Let's not mention Daniel again," I said. "He was using me to escape his dull life." "Sound like you were made for each other, then," she said. "I wasn't using him!" I protested. "Then what were you doing sweetie?" she asked. "Getting to know him. Thinking what it might be like to see him longer term. You know, whatever people date each other for." There. I had admitted it. I liked Daniel, and I wanted to see him again and get to know him better and find out if we might have fun together. Susie was silent for a moment. "Then I'm very sorry that he hasn't called. You're a very sweet boy, and he's missing out on something wonderful." Monday was a relief: everyone was unhappy at the weekend being over except me. I went to class, did some school work, went for a run, and generally had an ok time. Tuesday was better still, and I told myself that I didn't need Daniel and his kinky clubs or even New York City. I could be happy right here in rural New Jersey, and I would prove it to myself by finding a girlfriend and we would do our school work together and go to the movies and the diner and stuff. It would be nice in a quiet, comfortable, semi-comatose sort of way. But by Wednesday evening the weekend was looming large again. It's a matter of my outlook, I told myself. You just think everyone else is having fun, but they really aren't. They're just telling themselves that they are. But that didn't work: I'd swap telling myself I was having fun for not having any fun at all. As weekends go, a little self-delusion might not be a bad thing. Thursday came and went. By Friday the gloom was deep around me. I went home from school and closed myself up in my room, ready for the weekend. I fell asleep about nine. An hour later, my phone rang. I answered it without looking to see who had called. "Hi sweetie!" Susie said. "Hi," I said sleepily. "So what did he say?" she asked. "Who?" "Daniel, of course." I was confused. "I haven't heard from him," I said. "That's odd," she said. "I saw him this afternoon and he said he was going to text you." Suddenly I was awake. "He did? What about? What is he going to text me about?" "I don't know. He didn't tell me." "You didn't ask?" "What sort of yenta do you take me for?" Susie asked. "When was he going to text?" I asked. "He didn't say." "And you didn't ask. I know, I know," I replied. "Well let me know when he does," she said. "I can't wait to find out what he says." "Of course, Susie," I replied. "And no, I don't think you're a yenta at all." "I'm only looking out for your happiness, baby brother," she said. "And that's why I love you so much," I replied. "You love me because I persuade you to do kinky things," she said. "That too, sweetie," I said. As we hung up, it struck me that Daniel might not be getting in touch to suggest that we get together again. He might be writing out of politeness to tell me that he doesn't intend to see me again. But, I thought, either way I can live with it. Closure is a good thing, right? Yes, I replied, although not totally believing my answer. But it wasn't closure, at least not yet. "Hi Stephanie," he wrote. "Sorry about being out of touch. I was in Boston last weekend for a family event, and this week was crazy at work." Lame excuses, I thought. But I read on. "Are you free to meet in the city Sunday afternoon? Maybe I can meet you at Susie's and we can take a walk in the park if the weather's nice." My mind suddenly filled with an image of us walking hand-in-hand through Central Park, the sun shining, a gentle breeze blowing, passersby smiling benevolently at us. Not so fast, I told myself. Does he really think I'm going to rush to say yes after how he's ignored me for two weeks? So I called Susie back and read her his text. "You're going to ask me what I think you should do, aren't you?" she asked. "No. I know what I'm going to do," I said. "Hurray! A boy who knows his own mind," she said. "You'll go far in life with that outlook, young man." "I'm going to meet him and go for a walk with him," I said. And if we see each other again afterwards, that'll be great. And if we don't, then I'll live with it. I'm not going to get upset about him again. It's his last chance." "That's the spirit," Susie said. "We girls have got to be strong. So I'll see you Sunday morning?" "Yes," I said. "And think of something super slutty for me to wear." "Wow!" she replied. "Only too glad to help." I replied to Daniel. "Sorry you had such a busy week," I typed. "Yes, let's meet Sunday." Suitably unenthusiastic, I thought. A New York City Romance CHAPTER SIX I took the bus to the city early Sunday morning. It was dark and overcast with a few drops of rain. So much for my dream of a sunny day. I texted Susie: "I'll need a slutty raincoat too." "Yes, so does the rest of the world," she replied. "Tell me when you've invented one." When I arrived at her apartment, she pointed to a white raincoat. I tried it on. It was short, and cut slim at the waist, but it wasn't how I had been intending to dress. "It's cute," I said, "But not . . . sexy" "How much you have to learn, little girl," Susie said. "Cute can be very sexy when cute is combined with slutty." "What? Maybe you have a slutty hat I can wear with it?" I asked, giving her a look. "No," she said. "But you haven't thought about what might go under it." "I'm listening," I said. "Tell me more." "Well how about a really short skirt. Or maybe some very skimpy and very tight shorts? Or a short tank top that exposes your tummy or your cute shoulders?" Susie took some clothes from her closet and laid them on the bed. "What do you think" she asked. I liked the miniskirt very much. It was black, and pleated, and very short. And it would go with the short white silk blouse that would lift up and expose my stomach when I stood up straight. "Ok then. Undress," Susie instructed. "It's makeup time." She sat on the bed watching me undress. I stood in front of her naked, my cock already hard. Susie's eyes looked over my body and a big smile formed on her face. "Sweetie! You've shaved!" She ran her hands up my thighs and between my legs. "So smooth," she said. "If I was a boy, I'd want to take you home and run my tongue all over that smooth skin and cute little cock." "So why not pretend that you're boy and do it now?" I asked. "Do you really want me to" she asked. "Yes, of course I do. Has there ever been a time I didn't want you to touch my cock? "No. But I thought that you might not want to today. You know, in case anything happens with Daniel." "Like what?" "Like sex, dummy! Don't tell me you weren't thinking about being undressed by Daniel when you were shaving your legs and around your pretty little cock." I couldn't say I hadn't. "Well, you know what they say about a bird in the hand," I said. "I'm the bird in the hand?" Susie asked. I nodded. "Well don't blame me if you can't get it up later," she said, leaning forward and taking my cock in her hand and drawing me towards her. A while later, sitting in front of the mirror, Susie applied makeup to my face, and arranged my hair. "Now for your clothes," she said. "We haven't yet chosen your panties. What would Stephanie like to have next to her pretty little cock today?" "I was thinking about a pair of your boy shorts," I confessed. The skimpy ones cut high at the back." Susie pulled out a white pair, and I pulled them on and looked at myself in the mirror. "Very nice," she said. I felt my cock stirring again as I watched myself being transformed. "Try this too," Susie said, handing me a matching white camisole, cut very short so that reached down just below my nipples. Then I put on the skirt and blouse. I looked at Stephanie in the mirror. She really was very pretty, I thought. "So now try on the coat again." Susie said. Unbuttoned, seeing my skimpy clothes under the coat was exactly as she had promised: cute with a flash of slutty. I stretched and my skirt lifted up to expose my panties and the blouse rode up over my tummy. "You catch on quickly," she said. Daniel texted me a few minutes later to say he would be there very soon. I kissed Susie, buttoned up the coat, and walked down to the street to wait for him. It was raining softly, and I sheltered in the entrance until his cab pulled up. Daniel opened the door and called for me to get in. I sat down next to him, being careful to not let the raincoat expose too much of my legs. That can wait, I thought, for the right moment. "Do you still want to walk in the park," he asked. "Yes, if you do," I said. He pointed to his umbrella. "Let's do it. If the rain gets too heavy we can go for a coffee or something." The cab let us out at Columbus Circle and we walked into the park sheltering under his large umbrella. There were a few people about, mostly couples under umbrellas. We walked along a path through the trees, not saying anything. I wanted to break the silence, but I held back. He's the one with some explaining to do, I told myself. After a few minutes walking side by side, Daniel spoke. "I'm sorry I didn't write to you for so long." "You were busy," I said, helping him out. "And you had a family event." "Yes, but that wasn't really the reason," he said. "So what was it?" I asked. He was quiet for a while. I was patient. "I didn't know if I should see you again," he said. I wondered what he meant, but I thought I knew. "I had such a great time with you when we went dancing. You're so much fun. And you're so pretty," he said. "And I so much wanted to see you again. But . . ." "But . . .?" I asked. "You're not like other girls," he said, smiling at me. "I didn't know whether I could take that step. Where it might lead." "So where might it lead?" I asked, returning his smile. "I have no idea!" he replied. "I wasn't able to work that out." "Me neither," I said. "But I don't mind not knowing." "But I've always had a plan," Daniel said. "Everything I've done, I've had a plan about how to accomplish it, and when I've accomplished it, what the next step is. High school, college, medical school, internship. It's all been carefully planned. It's not in my nature to not have a plan." "You've never dated anyone without knowing how it's going to end up?" I asked. "Of course," he said. "But with you it's different. It's a step into the unknown." "So what's the worst that can happen? We find out we don't like each other so much and stop seeing each other. That's not the end of the world, is it?" "It's not that simple," he said. "Being with you makes me different. It changes what I think of myself. You don't realize how dull I really am! Being with you made me feel like a totally different person. I felt I was suddenly adventurous and exciting. I was taking a risk, crossing a boundary. And that's not me. I'm a doctor! I'm as conservative as anyone can be." We were silent for a while as we walked along the path, the rain falling gently on the umbrella. "So I didn't write. I'm sorry," he said. "I should have called you and told you what was going on." "That would have been nice," I agreed. We arrived at the lake and stood under the umbrella watching the raindrops splash into the water. "So?" I said. "So?" he replied. "So where did all your hard thinking lead you?" "To this spot here, right now, with you." He turned to face me. "For all my thinking, I couldn't get over one thing. I want to be with you." We looked into each others' eyes, both smiling. "So can I kiss you again?" I asked. He leaned forward so I could kiss his cheek. "I've been thinking about your first kiss," he said. I stretched up and kissed him lightly on the lips. "That one was nicer," I said. And we kissed again, this time our lips opening so our tongues could explore each other. My hands went to his waist to support myself as we kissed. He held the umbrella above us, and his free arm went to the small of my back, and pressed me again him. We stood there, leaning against each other, for long minutes. We walked on. Daniel took my hand. "So what about you?" he asked. "No doubts?" "None," I said. "I liked you when I met you, and I loved our first date." "Wasn't that club great?" he asked. "We should go there again." "I'll go anywhere you want," I said. "Especially somewhere that exotic." "Yes, it was an eye-opener wasn't it," Daniel said. "I guess I've led a pretty sheltered life." "That's my task," I said. "To awaken the kinky side of your personality." "You're sure I have one?" he asked. "We'll have fun finding out," I said. "What's the first step?" he asked. "The first step is you inviting me back to your apartment?" "Now? Would you like to go there now?" he asked. He sounded surprised. Nervous even. "Is that an invitation?" I asked. "Dear Stephanie," he said, "I would like to extend to you an invitation to visit me in my apartment. Is that a proper invitation?" "Dear Daniel. I am pleased to accept your kind invitation," I said, and gave him my hand. We walked out of the park, and flagged a cab. I got in first, and undid the lower buttons of my rain coat, and stretched out my legs. Daniel eyes went to my bare legs, settling on my thighs. My skirt barely hid my panties. "You have beautiful legs," he said. I smiled what I hoped would be an enigmatic smile. "I'm glad you like them," I said. The cab stopped outside a modern apartment building a short ride from the park. We walked through the lobby to the elevators. We got off the elevator and walked to Daniel's apartment. When we reached the door, he turned to me. "Are you sure you want to do this?" he asked. "What is the 'this' you're referring to?" I asked. He smiled. "I don't know," he said. I kissed him gently on his lips. "So let's go in and find out," I replied. He unlocked the door, and we went in. I sensed his nervousness, and it excited me. He locked the door, and I kissed him deeply. Free now from the umbrella, both his arms held me by the waist and pulled me against him. "Take off your coat," I told him. He took it off, and took me in his arms again, and I could feel his hard cock press against me. I stepped back and looked at him. His polo shirt showed of the defined contours of his shoulders and chest, and his jeans showed off his erection, pressing hard against the fabric. I put my hands on his waist, under his polo shirt, and lifted them up to his chest. "You have a great body," I murmured. My hand went around to the small of his back, and slipped a couple of inches into the back of his jeans. I pulled him towards me again, pressing my body against his erection. He gasped at the touch, and we stood pressed together kissing, my slight movements against his body causing him to emit deep sighs of pleasure. "Daniel, where's your bedroom?" I whispered. He led me there. "Sit on the edge of the bed," I told him. He did. "Take off your sneakers," I said. "And then your shirt." I stood in front of him, a few feet away. Barefooted and bare-chested he seemed so vulnerable. I started to unbutton my raincoat, beginning at the top, working slowly downwards, all the while looking at his face to see his reaction. I took the coat off my shoulders and dropped it to the floor. "Oh my god," he said. "You are so incredibly sexy." "You like my skirt?" I said, turning around so he could see how it looked over my ass. "Yes, it's amazing on you," he said. I faced him again, and stretched my arms high above my head. My skirt and blouse lifted up, exposing my body further to his eyes. Daniel stood up and gently pulled me to the bed. He sat on the edge, and I straddled him, sitting on his lap facing him with my legs either side of his body. I kissed him, on the lips, on the neck, on his chest. My mouth moved to his nipples and caressed them lightly with my tongue. My hands moved to his stomach, exploring him, then settled on the top of his jeans. I slowly undid the button and lowered the fly. His cock sprung out, hard and big. We both looked down at it, asserting itself between us. I leaned forward and whispered in his ear, "Can I touch your cock?" "Yes," he replied. "Please, Stephanie!" I took his cock in both my hands, encircling it, rubbing it with my palms, feeling its hardness and its size. Then, with long slow strokes, my hands moved along its length. At the top of each stroke, I squeezed his bulging phallus, forcing out a little stream of clear liquid onto my hands. "Am I doing this right?" I whispered. "Yes, it's amazing," he replied between moans. His moans and the growing tension of his muscles told me he was going to cum soon. But I wanted him to be naked before that happened. I let go of his cock, and kneeled before him. I took each leg of his jeans and pulled them off. Then I looked at his naked body, and my cock gave little pulses of excitement. I ran my hands up his calves and thighs, pressing my fingers into his tense muscles, until they were back where I wanted them to be. I took his cock with both hands and drew it to my mouth. I kissed it softly, then caressed it with my tongue. Then I lowered my lips over the bulging tip, enveloping it in my mouth, exploring it with my tongue. Daniel's hands held my head, his fingers running through my hair. My hands continued stroking his shaft as my head moved up and down on him. He came in my mouth, his cum spurting in me, again and again and again. Daniel's moan got softer and slowly died away. He looked down at me, his cock still in my mouth. Then he took my arms and pulled me up onto the bed, holding me on top of him, my chest on his, his cock warm and wet against my thigh. We kissed, softly and deeply. "That was wonderful," he said quietly. "It was," I said. "You have an amazing cock." "And you have an amazing mouth," he said, kissing me again. "It's barely big enough for the task," I said. "And I thought I might drown with all that cum." "Is that really the first time you've done that?" he asked. I gave him a coy smile. "Do you think I'm the sort of girl who regularly sucks cocks?" "No, that's not what meant," he said quickly. "I was just wondering, you know, if I was your first boyfriend." "Yes sweetie, you're the first," I said. "Would you like a certificate?" "Maybe," he said. "I could frame it and put it next to my medical license." "Or maybe I should just give you a t-shirt, with a picture of me kneeling between your legs sucking your cock." "I would love a picture of that," he said. "Something to remind me of you during the week." "You'll need a reminder after what we've just done?" I asked. "Speaking for myself, I don't think I'll quickly forget it." I lay in his arms, kissing him, and felt his cock start to grow again. I slid down on top of him so my cock was pressed against his stomach. His hands reached down and lifted up my skirt and his fingers explored my ass. We moved slowly together, my cock rubbing against him, his cock rubbing against my ass through the thin fabric of my panties, and my lips softly kissing his nipples. Then Daniel flipped me over on the bed. He sat next to me, looking down at me, his cock hard again. He undid the buttons of my blouse and took it off. I lay back on the bed, my stomach and abdomen exposed below the skimpy camisole still covering my nipples. He leaned over and kissed me, and ran his tongue from my stomach upwards towards the camisole. He lifted it up to reveal my nipples, and then sucked them until they were hard. His tongue ran down my body again. He pulled my skirt down a few inches to expose the top of my panties. My excitement grew with each inch of my skin he revealed. I wanted him to undress me completely so I was totally exposed to him. Daniels's hands undid the clasp of my skirt, and he pulled it down over my legs. Now my hard cock was open to his gaze, straining hard against my panties. His hand slipped between my legs, pressing gently against me, and he kissed my cock through my panties. My back arched to press my cock harder against his mouth. His hands went to the top of my panties and he slowly pulled them down over my thighs. Then he kneeled on the bed between my legs, and pulled me towards him so our cocks touched. He took us both in his hand and stroked us both together. We came together, our cum mixing as it spurted over both our cocks. I lay with my head on Daniel's chest, our wet cocks pressed against each other, Daniel's arms holding me to him. "Daniel," I said. "Yes, sweetie?" he asked. "Nothing. I just like saying your name." We lay together for a long time. There was no need to speak, not at that moment. It was getting dark outside. I needed to leave soon to catch my bus. But not yet. I wanted to enjoy this moment for a while longer. My phone rang. I got up from the bed and fished the phone out of the raincoat pocket. It was Susie. "Hi sweetie," she said. "Just wanted to check you're ok?" "Yes," I said. "Everything is great. I'll be back in a few minutes or I'll miss my bus." I lay down on top of Daniel again. "I've got to go," I said. "When can I see you again?" he asked. "Next weekend," I said. We kissed again. I stood up and gathered my clothes. "Wait," he said. "Before you get dressed." He took my hand and led me to a full length mirror. We stood side by side, hand in hand. "Don't we look good together?" he asked. We did. Very good. Our cocks grew hard again as we stood there. "Take a picture," I said, handing him my cellphone. Daniel watched me as I got dressed. "Time to leave," I said. He quickly dressed, and we went to the street to find a cab. When we arrived at Susie's building, Daniel got out of the cab with me. "See you next week, Stephanie, sweetie." he said. He took my hand and squeezed it, and got back in to the cab. I hurried upstairs. "So?" Susie asked. "So? What happened?' "This," I said, showing her the picture Daniel had taken. "This and a lot more." "Stephanie, sweetie! I'm so happy for you. Was it wonderful?" "It was amazing," I said. "And I'll tell you everything, but not now. My bus leaves in twenty minutes." I undressed and removed my makeup, then quickly dressed in my jeans and t-shirt. I kissed Susie. "Thank you so much," I said. "For what?" she asked. "For being my friend. For making me dance with Daniel. For making me look so pretty that I had the confidence to do this. For your clothes. I'm sorry that the panties are rather wet," I said. "We'll have to get you some of your own," she said. "Or maybe Daniel and you should go shopping together." I caught the bus with a couple of minutes to spare. It was dark by the time we got through the tunnel into New Jersey. I took out my phone and looked at the picture of us together, my arms around Daniel's waist and my head resting on his shoulder. I looked at his smile, his beautiful body, our cocks touching, both of us erect. I opened an app on my phone and annotated the picture. "This is to certify that Daniel's cock was the first I ever sucked," I wrote. "And that he came in my mouth. And it was wonderful. And I want to suck his cock again. And again and again and again. xxx Stephanie." I sent it to Daniel.