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.