Home Run, Part 1: At Bat free porn video

Home Run By Pamela ([email protected]) Part 1. AT BAT I think if I were just a little less smart and a little less shy then I wouldn't be about to enter graduate school at nineteen years old having never had a girlfriend. But no, I skipped second grade and then skipped eighth grade and because that made me so much younger than my classmates, I became pathologically shy. So shy, that I found it excruciatingly difficult to talk to girls, let alone ask them out or become friends with them. Since I had no relationship with girls except my much older sister, Lei, and have always been a lot younger than the guys in my classes, I've managed to slip through my childhood knowing virtually nothing about sex and particularly what it is that boys and girls do with each other. And yes, my dad is not the sort to explain the birds and bees to his son, so he has never taught me anything either. The only knowledge I've gotten is from some movies and books, but it is all abstract. I see people kiss, for example, but I've never done it with a girl and have no idea how to do it properly. High school was particularly difficult for me since I had to watch the girls as they changed into women. I could see that they were often excited about wearing their first bras or having the bittersweet pleasure of having their first periods. I felt a burning desire to have a girlfriend who could confide in me what she was experiencing as she became a woman, but none of the girls I knew regarded me as anything more than a kid brother. What did their newly forming breasts look like? I hadn't the slightest idea of what a vagina looked like or how one behaved. I had only the vaguest idea of how girls used pads or tampons to catch their blood flow each month. How did boys get their penis inside girls? I had no idea how such a thing could be made to happen. As each month went by in high school and the girls developed curvaceous bottoms and bulging breasts and began wearing pantyhose and heels and short skirts, my desire to have a girlfriend intensified. The craving for a girlfriend became so strong that somewhere along the way I realized that I could sort of have a girlfriend by "dating" myself. I would play the part of my own girlfriend and to do that I would have the help of wearing my mom's clothes so I would at least sort of look like a girl. To be honest, I found that I really enjoyed this game. It was fun to pretend to be my own girlfriend. I'd give myself a name, usually Audrey for some reason, instead of my real name, which is Martin. I would pretend to be a girl who really adored Martin and wanted to please him. For example, since Martin liked feminine girls, I tended to wear my mom's sexiest underwear and one or another of her floral pattern dresses. So attired, I would mince my way around the house having a conversation between myself and Martin: "Audrey, I've never seen you prettier than you are now." "You're such a dear, Martin. I love dressing up and being pretty for you." "You're wearing such a lovely dress." "I'm glad you noticed. You make me feel so desirable. I'm quivering with love for you. Come hold me!" The end result of games like this was to make me feel intensely feminine which had the benefit of calming my frustration in not having a girl friend. I could look forward to having Audrey show up about once a week, and that seemed to be enough. However, my expectation was that the day I got a real girlfriend would be the day that I said goodbye to my pretend girlfriend. I hoped that when I went to college, I'd finally be able to get a real girlfriend. When I was applying to colleges my parents felt that I wasn't ready for dorm life, so it was decided I'd live at home and attend the pretty decent state college that was a mile away from our house. By this time, I was so accepting of my social awkwardness, and pretty content to have my weekly dressing up game, that I didn't fight them about it. I'd have my mom's clothes in case I couldn't meet a girl and there was a certain amount of comfort in that. Surely, in a dorm, I could never play my dress-up game and so there was quite a risk that I'd end up lonely and miserable if I went away to college. In college I did make some friends though they were all guys and though they tried to help me find a girlfriend it never worked out well. I'm not unattractive, but I look quite young and I'm fairly thin and just 5 foot 8 inches tall and painfully inexperienced. I'm sure my cluelessness in knowing what to say to girls, or in knowing what steps to take in getting a date, had a lot to do with my failure in the love department. All during college I continued to play my dress-up game and I became quite adept at being Martin's girlfriend. I spent a lot of time looking at girls, studying everything they do and then imitating it. I particularly enjoyed watching girls making very girl-like gestures with their hands or when they walked, and I'd try to imitate these motions. As much as I liked acting like a girl, however, invariably there would reach a point where reality would set in and I'd be frustrated. For example, though I'd be wearing my mom's bra with the cups stuffed with her panties, the moment I felt inside the bra I'd know that there was no breast there, just panties. Also, there was never a vagina inside my panties, just a penis and it was disconcerting to say the least to pretend one didn't have a penis and then find out that one did. In such moments I wanted to have a real girlfriend in the most awful way. I had a fantasy of her being my friend, my buddy, and someone who when we held each other and felt sexual, I would find that she had real breasts and a vagina and not folded up panties and a penis. **** Now I'm graduating college and I'm as innocent of girls as I was in high school. I keep thinking that I ought to ask my dad about girls, but I'm afraid that he'd be upset that I never asked him before. In addition, I've never been close to him since he's a macho guy and I'm not. He has an abundance of testosterone that gives him expectations for my athletic ability that are way beyond what I can achieve. When I was young, he often would grow frustrated trying to teach me to comfortably swing a bat or shoot hoops in the manner of a typical boy. He'd remind me over and over again. "If you swing the bat like a girl, no girl will ever want to date you. You've got to be a good athlete if you expect to charm the ladies." When he'd say something like that, I'd become more convinced that no girls would like me and at the same time I wanted more and more to seek out the comforts of my mom. Besides the affection she gave me, I, of course, had a secret connection to her from the fact that I dressed in her clothes. In some of my fantasies, in the role of Martin's girlfriend, I'd be meeting his mom, and she would say something like, "What a coincidence, I have a dress just like that!" It's somewhat ironic that while I would love to have a girlfriend who could help me improve my pretend-girl persona, if I had a girlfriend, then I wouldn't need to pretend I was Martin's girlfriend. In any event, if I ever do get the chance to ask a girl about how to be a girl, then I'd have a million questions I'd want to ask her. I would like to find out what girls feel like when they wake up in the morning. Or what they feel like brushing their teeth or going pee pee. What do girls feel like getting dressed, like when they put their breasts in a bra, or are walking to school, or being on a date with a boy? What do girls feel like when they listen to music or when they dance? I want to know the answer to all these questions so that I could feel the same way that they do and then my girl-pretending would get more and more accurate. When I do get the courage to talk to a girl, like one who may be sitting next to me in class, I don't know whether to talk to her as if she might become my girlfriend or talk to her as if she would be a consultant on how to be a girl. This has made me even more self- conscious than I normally am so that even though I usually have many things on my mind to talk about, my mind invariably goes blank when I'm supposed to say something to a girl. Not one subject comes to mind to talk about. Instead, I usually contemplate whether I should run for my life and hide. Faced with this strange silent guy, girls lose interest in getting to know me. **** While I didn't have a girlfriend in college, I did have a rich academic life and I decided that I wanted to become a mathematician. In fact, a very specific sort of mathematician which meant that I would be going to graduate school at Columbia University in New York City to study with Professor Oppenheim who is the preeminent expert in my sub- specialty. In fact, in just a couple of weeks I'm moving from our midwestern town to New York City to get an early start on my graduate career. I'll spend the summer working on a scholarship with Dr. Oppenheim even before I start classes in the fall. I'll be living far from home all by myself in a big city that I don't really know much about. A shy, brainiac kid who tends to envy girls and is too shy to talk to them. As I've hinted at before, I'm fully expecting that I may go through some sort of melt down over the fact that I will no longer have my mom's clothing to play with. On the other hand, maybe I'll finally meet a nice girl who will become my girlfriend. In that case I'll be really glad that I don't have my mom's clothes nearby, since they would tempt me to compete against Martin's real live girlfriend for his affection. Just think how crazy that is! Admittedly, I'll probably be a bit sad to give up my pretend girlfriend for a real one, but hopefully those feelings will eventually be buried underneath all the wonderful things that come from having a real girlfriend. My mom has been terribly nervous about sending me off alone to the big city. Even though Columbia has a nice dorm I can stay in for the summer that has guards and food and medical care and anything else I might need, she worries incessantly about me being so young and vulnerable compared to the other graduate students. The truth is I'm also worried about being alone in the city but only because I think I might not make any friends, so I'll become very lonely. And on top of that I will have no chance to pretend to be Martin's girlfriend. **** With all this worry about me being alone in New York, my mother decided to call her old college roommate Miriam who happens to live very close to Columbia to see if she would be willing to be an emergency contact for me if I were to get into trouble. My mom and Miriam have kept up their friendship over the years, never going more than a year or two between visits with each other. Miriam is a very successful clothing buyer for Allied who has never married. My mom has visited Miriam a few times in New York and Miriam has visited us on several business trips that took her to the Midwest. I had last seen Miriam, or really my "Aunt" Miriam as my sister Lei and I call her, about a year or two earlier. Miriam is very beautiful, like a movie star, but also modest, kind and thoughtful. Though middle aged like my mom, she has retained a youthful frame of mind and appearance. Unfortunately for me, it is painful for me to be around her since she has a female charisma that reminds me of how much I am missing. Besides her shapely feminine body, her movements are graceful and delicate, her hair is long and styled and bounces when she walks. If I had a girlfriend like her, I would be the happiest boy alive. She has also been a useful resource in my quest to learn female behaviors that I can imitate when I'm pretending to be Martin's girl friend. For example, I've observed the way she tucks her skirt under her as she sits. I especially like the way she does this when her skirt is tight because she has an especially girlish way of smoothing the skirt just as she bends her legs to sit. I've studied the delicate straps on her high heels and wondered how she buckles them. This has sparked my interest in my mom's high heels and I regularly wear them in the role of Martin's girlfriend. Of course, Miriam's pantyhosed legs are a wonder in their own right. When my mom called Miriam to ask her to be my emergency contact, I stayed close enough to the phone to overhear her side of the conversation. I figured that at some point, I'd probably meet up with Miriam once I got to New York and while that might be sort of traumatic, I knew I'd survive the encounter. Miriam had a busy professional life and no doubt we would not get into regular contact with each other. I heard my mother greet Miriam saying, "Hi Miriam, its Lillian." They exchanged some pleasantries and then my mom said, "I want to ask you for a small favor." "Do you remember from the last time I spoke to you that Martin's first choice for graduate school is Columbia?" My mom listened and then said, "He did and we're so proud of him. In fact, the reason why I'm calling is that Martin is actually leaving for New York next week because he's got a position doing some research with a math professor during the summer." Miriam said something and then my mom continued, "The thing is Miriam, he's going to be in the dorm but I'm a little worried that he doesn't know anyone in New York if he should have a problem. Would you mind if he could list you as his emergency point of contact? It would take away some of my worry." I watched my mom's face to see what Miriam might be saying. Miriam seemed to be giving a speech about something and my mother said, "Oh, no, Miriam, you don't have to!" Then a minute later, "That is so very kind of you! Look, Martin is nearby here, why not tell him yourself." My mom said, "Miriam wants to talk to you." Puzzled and not a little bit nervous, my mom passed me the phone and I said, "Hi Aunt Miriam." "Hi Martin! Your mom told me the great news about you going to Columbia. I was telling her that the dorm will likely be a ghost town during the summer and that you should come and stay with me for the summer. Then in the fall you can go to the dorm when all the kids show up." Reeling with surprise I said, "Oh, but Aunt Miriam, I can't impose upon you like that!" "Pshaw, Martin, it's the least I can do. I have a large apartment with plenty of space and I'm only a few blocks from campus. You and I will have a wonderful time together. How about it Martin, won't it be exciting?" I felt like I was going to faint. How could I ever share an apartment with Miriam? To be physically near her on a daily basis? To have to look and talk to her, to see her feminine persona up close and somehow find a way to act normal. There would be nothing to save me from my desire to be her boyfriend. How in the world would she not see that her femininity was overwhelming me? She'd have to tell my mom and dad that I was a sorry excuse for a boy. My nerves shot past their limit and I felt myself slipping into a panic attack. I made a sort of strange grunting sound and Miriam said, "Put your mom back on honey," and I handed the phone back to my mom. The two of them talked some more and my mom covered the mouthpiece and said to me, "What do you say Martin?" Seeing how there was no way out of this without hurting Miriam's feelings and getting my mom to freak out and demand some sort of explanation from me, I shrugged my shoulders giving a kind of weak "yes" answer. "Martin tells me he is absolutely delighted to stay with you. It will be so wonderful for him. It will take away all his anxiety about being in New York alone. You're sure it won't put you out?" As I listened to the conversation, I heard my mom and Miriam putting the plan into motion. I heard my mom tell Miriam that "Martin is a bit shy, but I'm sure that he'll warm up to you in a short while once he hits the ground in New York." "You're so sweet Miriam. What a great friend. I can always count on you!" The two women talked for a few more minutes and then my mom said goodbye. My mother looked at me smiling and said, "I am so relieved. You'll have such an easier time adjusting to New York under her guidance. Her apartment is beautiful, and you'll have your own bedroom and bathroom. In fact, she has brand new lacquer furniture for your bedroom that is imported from Italy that will be coming in a week. So, it will be a very elegant room for you to stay in." I smiled as best I could and said to my mom, "I'll try as hard as I can to be appreciative to Aunt Miriam." My mom smiled and said, "That pleases me no end. I am sure that you'll find Miriam to be truly delightful. You'll surely end up being very happy to be staying there." **** The next day Martin's mom called up Miriam to thank her again for her generosity. "I also wanted to tell you that Martin's dad and I are hoping that this whole experience for Martin, being in a big city with lots of people to interact with, will help get him out of his 'shell.'" "I know how shy he is Lillian," Miriam said, "and I'll do my best to help him relax and feel comfortable." "It's particularly with girls that we are most concerned. If the truth be told, Martin has never been on a date, nor attended a dance or been invited to a party. His dad and I worry about how frustrated he is. We know that he would love to have a girlfriend or even a girl to talk to." "So maybe I can be a big help in that department." "You know some young girls his age?" "There are some girls at work who I could possibly invite over here for dinner. Regardless of that, I'm thinking that for Martin to camp out in a woman's apartment and have daily interactions with the opposite sex, even if I am older, might help him get more comfortable talking to girls." "I agree Miriam. I was a little bit afraid to mention that because that is really putting a burden on you. His shyness could become a problem for you, and also..." "Nonsense, Lillian, I think no matter how it unfolds; it will be fun for me. I like young people and anything I can do to help Martin will be nothing but a pleasure for me." "Thank you, Miriam, but I was about to add that Martin's dad has never even explained the birds and bees with him. We wonder if Martin even knows anything about sex." "Then, if any opportunity arises to get him exposed, I won't stand in his way. Perhaps he could make friends with some boys who could open up his eyes." "That's great Miriam, but actually..." Lillian paused for a second and Miriam said, "What dear? You can confide in me." "I know Miriam. I feel a bit awkward saying this, but you know that you're very beautiful and I expect that a boy like Martin could form a crush on you." "Oh, please, Lillian," Miriam laughed. "No, I'm serious and I'm not saying it's bad for him to have a crush on you. In fact, the opposite. It could give you an opportunity to direct Martin toward understanding girls, how to meet girls, how to feel comfortable with girls. You know, all of that. He'll trust you and you can use the fact that you're a woman who he talks to, to help him grow up. Really, anything that you could do to help him overcome his ignorance and shyness around girls will make him a happier person and will make his father and I very happy." "I'm flattered that you'd trust me with such an important mission. I'll do my best to help him any way I can!" "Thank you, Miriam, I really appreciate it!" **** A week later Miriam called my mother to say that the fancy Italian furniture that she was expecting was going to be delayed a few months because of a strike. She had another bedroom that she could put me in, but she wanted to talk to me about it. My mom handed me the phone and Miriam said, "I was telling your mom that my guest bedroom is presently unfurnished. I had gotten rid of the bed that was in there to make room for the new furniture. But that can't get here until the fall. However, I can put you in my other bedroom, it's my niece Penelope's bedroom, the one that she uses when she visits me, but she's away for the summer and won't be coming by." "I guess as long as she doesn't mind it's OK with me to stay there," I said. "Oh, it's no problem for her, but the thing is that she's the one who decorated the room and it is a bit feminine in appearance. I can well imagine that a lot of boys might get a little irritated being surrounded by a lot of pink and some frills." "You don't think I'm going to like it?" "No, no, no, not at all. I personally don't see why anyone boy or girl wouldn't like the room, it's very comfortable and has its own bathroom. I just didn't want to surprise you." "Well, I guess, if it's no problem for you, then I don't see why it should be a problem for me." "Good, good, good, all good," Miriam said. When I got off the phone my mom said, "Miriam told me about the feminine decor. It won't bother you will it?" For the first time in my life my mom and I were talking even the slightest bit about anything having to do with my sexual feelings and I blushed and said to her, "Aunt Miriam doesn't think it's a problem so I said it'll be OK with me." "Great, Martin, you have become such a mature young man now!" **** I arrived in New York a week later on Sunday. The taxi let me out in front of Miriam's building. I felt a panic attack coming over me as I contemplated pressing the buzzer for her apartment. Unfortunately, I had no plan B; I had no choice but to ring the buzzer, so I reluctantly pushed the button. A second later I heard Miriam's voice over a speaker telling me that she would be right down. A minute later Miriam came into the vestibule and greeted me with a big smile. "So great to see you Martin! How was your flight and the trip from the airport?" I stared at Miriam in a state of disbelief. Whatever my memory was of how she looked; it did not do justice to the person in front of me. Whereas she had always been dressed somewhat formally in skirts and blouses when I had seen her before, now she was dressed more casually wearing a tight, white, short-sleeve blouse through which I could see the outlines of her bra and her large breasts. And she was wearing tight jeans that framed her perfect butt. I could barely look at her and yet I couldn't take my eyes off of her. Miriam raised her eyebrows and tilted her head as if to remind me to answer her question. I mumbled, "fine." "I'm so glad," Miriam said chuckling. Miriam helped me carry my luggage up to her apartment. I followed behind her walking like a zombie. When the door shut behind us and we were standing together in her living room I felt my knees lock and I was frozen in place. My heart palpitated and I could feel some muscle in my leg shaking nervously. All my fears took root at once. My fear of Miriam, my loneliness for my family, anxiety about meeting the professor I was to work with and an overall dread of adjusting to life in New York. Of most immediate concern was the fact that I needed to act like a human being with Miriam, not an android with a silly smile stuck on his face and no words coming out of my mouth. Miriam smiled at me and I looked down at the ground. "Make yourself comfortable Martin, I'll be right back." Miriam went down a hallway off of the living room to her bedroom. Nervously, I stood in the living room awaiting her return. The room was immense with a beautiful white leather sofa and armchair and a few interesting sculptures and paintings. A remarkable lacquer coffee table was in front of the sofa as well as an ottoman. Across the room was a large screen television. To one side was a dining area with a large table and beyond that the entrance to the kitchen. I heard the distant flush of a toilet. The image of how Miriam looked came to my mind and I felt a strong urge to flee the apartment. Before I could do anything, Miriam came back in the room. I stood awkwardly forcing myself to look at Miriam and trying not to focus on how attractive she was. She was smiling as if she thought the strangeness of the situation was amusing. "So, Martin," she finally said, "we have to get you situated." She picked up one of my bags and said, "Come with me." I picked up my other bag and followed Miriam down the hallway. She had the most beautiful hair. Kind of blonde, long and bouncy. I gazed at it and then my eyes took in the shape of her butt and the feminine way she moved. This was going to be much harder than I had expected. As we walked, Miriam said, "As I said on the phone, I have to put you up in Penelope's bedroom, which is just a wee bit on the feminine side. And as I said, it's no problem for me if it's no problem for you!" She led me through a doorway into her niece's bedroom. Whatever I had fantasized about being in a girl's room did not prepare me for the shock that awaited me. The bedroom was that of a girl who worshipped pink and anything and everything that was girlish. Frilly pink curtains were on the windows, the bed coverlet was white with pink roses and lace. A doll wearing a puffy pink ballroom dress with layers of crinolines decorated the center of the bed between the two pillows. The dresser was white with pink hearts at the corners. The floor had plush, rose colored carpeting and slightly pink wallpaper with thin white lines and sprays of daisies. Through a doorway, was an adjoining bathroom, with pink tiles, toilet, tub, wallpaper and towels. I was taken entirely by surprise. No daydream I had had in which I pretended that I was Martin's girlfriend included such a setting. Everything I saw around me tempted me with its siren song and I could feel myself blushing with embarrassment, as any boy would when ushered into such a purely feminine space. I couldn't grasp how Miriam could say it was just "a wee bit feminine." "You see you have a private bathroom," Miriam said pointing in the direction of the bathroom door. I nodded my head and Miriam continued, "apart from how feminine it's decorated, it's a really comfortable room. So, what do you think?" I looked at Miriam unable to talk. One part of me knew that the room was an answer to my prayers. It would provide endless opportunities to role play my imaginary girlfriend. But such thoughts made me feel guilty. Miriam would no doubt not want me in the room if I was reveling in how I could take advantage of the room to perfect my girl fantasies. Miriam's eyes fixated on mine and I figured she must be seeing the torrent of emotion in my face since she said, "I think you're aghast at the thought of staying here, aren't you?" "Oh, no, Aunt Miriam," I said finally able to talk, "it's fine. I was just a little bit surprised at all the pink. But I guess pink is Ok, it's just a color, right?" Miriam laughed and said, "How true Martin. I'm so used to the room I forget how unbelievably pink it is. And for a boy, wow!" Something in my face then made Miriam add, "I know many boys can feel a bit nervous around pink things, but as you said, it's just a place to sleep and it won't turn you pink!" Her small joke made me chuckle and loosen up a bit, and I could see that provided some relief for Miriam. She then continued saying, "I've cleared some of the drawers in the dresser for your clothes and there is some space in the closet I've left for you." Miriam opened up one of the sliding, accordion-like doors of the long closet revealing a small bare space on a clothing rack that was otherwise filled with dresses, skirts, blouses and a whole section devoted to pretty pink party dresses. There must have been a half dozen of them, each one in a plastic see-through garment bag, with large puffy skirts. Some of the garment bags seemed to have pink crinolines in them. I felt myself reeling as if I might faint. How could this be? How could such pretty clothes be in the same room as me? I would be able to pretend to be a much younger and prettier version of my girlfriend, that is, if I ever allowed myself to touch the clothes. Miriam walked over to the dresser and opened the top drawer and showed me that it was empty. She opened the next drawer down and I could see that the left half of it was empty and the other half was filled with what was clearly girls underwear. "You've got another half a drawer here. I hope you don't mind that I park some of Penelope's panties and bras here." I acknowledged Miriam's question with a slight grunt. My heart pounded at the sight of the frilly garments. That my clothes would be next to them, that I would be looking at them every day of the summer, seemed impossible. I concentrated with all my might on trying to figure out how Miriam could be so blas? about my sharing a drawer with her niece's bras and panties. She acted as if there was nothing out of the ordinary. "Very good. If there isn't enough room for your clothes, I can put the bras and panties somewhere else. Let me know. I want you to be comfortable here." I slightly nodded my head. Miriam suddenly smiled and looked at me. "You're so adorably shy and polite Martin. I hope you can treat the apartment like it really is your home this summer. Please don't feel like a guest. Relax and enjoy yourself." "Thank you, Aunt Miriam. I'll try to be less shy." I saw Miriam break out into a grin. "Aha Martin, you can smile!" I blushed and Miriam added, "Good. I think this is going to be the start of a very nice summer for both of us!" A few seconds later she added, "So why don't you relax here for a while getting used to the pink, and then when you feel ready come out to the living room and we'll get to know one another better. I'm very interested in hearing all about the research you are going to do at Columbia. How does that sound?" "OK," I said. Miriam left the room and closed the door behind herself. I lay down on the bed and let my eyes roam around the room. The reveries that I had had wearing my mom's clothes would be nothing compared to what I could do in this room. I could pretend that this room is where my girlfriend lives and then I could be that girlfriend. I could have fantasies in which she's getting dressed to go on a date with me. The possibilities were endless. It seemed as if Penelope must be very much like the kind of girl that I'd like to have for a girlfriend. She obviously loves being a girl and loves all the girlish aspects of being a girl. Being in love with femininity and appreciating her own femininity. Those were things that I probably would want in my girlfriend. Not that she was vapid, just that she appreciated all the things that went with being a girl. It was hard to believe that I had been thrust into this room. Me of all people and what's more, Miriam seemed utterly nonchalant about it. She acted like there was nothing too weird about it. Even having her niece's bras and panties in a drawer that I'd be using didn't appear to phase her. It made me wonder if I was much weirder than I already thought I was. After a while I got up and put my things in the drawers and closet. I stood a full minute staring at the bras lying next to my clothes and wondering if they might fit me. I had never met Penelope. If she wasn't especially petite, then there was a chance we might have a similar size. Of course, I would at some point end up touching one of the bras and I couldn't see how I could do that in good conscience. I'd be violating Miriam's trust in me and it would make her feel bad that she had put me in this situation. But, of course, how would Miriam know that there was anything to be concerned about? I went out to the living room as Miriam had suggested I do. She was seated on the sofa reading a magazine. She looked up at me, she had a pretty, slight smile on her face, and I felt the warm way in which she regarded me. "Have a seat Martin. Let's chat and get to know each other. So, what do you think of the room now?" "It's still pink, but I'm sure I'll get used to it," I said, half blushing. The image of the bras lying there came to mind. If only Miriam knew how much stress those bras would cause me. It had occurred to me that it was a bit strange that Miriam's niece had so many clothes awaiting her in a place that she didn't seem to visit often. I said, "Does Penelope come here often?" "Oh, yes, of course. She's also been studying in NY over the last few years and she comes by often. She's been coming since she was very young, and we are pretty close as far as aunts and nieces go. You must be thinking why does she have so many clothes? Well part of the answer is that she's studying to be an actress and she seems to often end up playing the part of feminine girls such as southern belle's or party girls. It's what she likes for herself, and I have somewhat indulged her proclivity toward frou frou." "It'd be nice to meet her," I said, feeling suddenly very daring. "When she's back from the summer I'll have the two of you get together. I think that's a wonderful idea! My two favorite young people!" I tried to imagine the kind of girl that preferred the pretty clothes I had glimpsed and the crazy pink everywhere. How lucky she is that she gets to immerse herself in her femininity. "I'm very interested in you, Martin. Tell me about your project here at Columbia." I told Miriam about the math research that I was to be involved with and why I chose that. A lot of the discussion was kind of technical, but Miriam was good at asking questions and she seemed to understand the gist of what I was saying. At more than one point she said, "You're such a smart young man Martin!". Eventually the conversation changed in which I asked her about her job in the fashion industry and about her history with my mom. I became very comfortable and relaxed to the point where I was sure this was going to be a great summer. Of course, it was a bit stressful to be in the presence of such a beautiful woman. I couldn't help but wonder about what her body looked like, or what I would see if she were to say suddenly lift up her blouse. When I wasn't thinking such thoughts and trying hard to not think such thoughts, my mind wandered to the pretty clothes in my bedroom. I knew that no matter how much I might tell myself to leave the clothes alone, I'd be exploring every inch of the dresser drawers and closet before the summer was over. And yes, Miriam went to work every day and I would have an ocean of time to play dress up as Martin's girlfriend. These thoughts made me feel increasingly guilty and also helpless. I prayed that I'd have the strength not to embarrass myself this summer. When there was a lull in the conversation, Miriam said, "You need to call your mom and tell her you got here safely." She led me to a phone in the living room and I dialed home. My mom answered almost immediately and was excited to hear that I had arrived safely. "How are you getting along with Miriam?" "Fine." "Really?" "She's nice." "I am so happy to hear that. You looked so mortally scared this morning." "I know mom. I was scared but I'm feeling a lot better now." "Isn't that grand. She's such a dear. How is your bedroom?" "It's kind of pink like Aunt Miriam said, but I think I'll get used to it pretty quickly." "I'm glad to hear that." We talked a little bit more and then she had me pass the phone to Miriam and the two of them talked awhile before they hung up. When she was off the phone Miriam said, "Your mom seems pleased that you've adjusted to life here so quickly. She was a bit worried about your shyness, but happily we're starting to put that all behind us." "Yeah, I guess I've always been kind of shy, mainly with girls I guess." Miriam looked at me sympathetically. "It's so hard being a teenager, isn't it? Particularly when it comes to the opposite sex." I blushed and said, "Yeah, I guess so." "At your age every little thing probably seems so monumental. The way a girl looks at you, or exactly what words she says. When you get older, you get a better perspective and its easier." I didn't know whether or not I should confide in Miriam, but I impulsively took the plunge and said, "I guess my problem has been that I'm so shy around girls that I never learned what to make of what they say or what it might mean by the way they look at me. It's all so hard to decipher." "Girls are people, just like you or me. It's just a matter of taking a risk and not worrying about getting hurt, even though that is a lot easier said than done." "I really wish I could take a risk, but I'm way too scared. I think I'll probably never have a girlfriend." "Such a handsome boy like you will certainly one day have many girlfriends. I guarantee it. I'm sure that there are plenty of girls who would love to be your girlfriend. I bet it's just that girls are shy the same way boys are, and you just need a little bit of luck at the right moment to get to know a girl." If it weren't for the fact that I was having an intimate conversation with a beautiful sexy woman, I might have found myself feeling so sorry for myself that I'd be crying. But there was something about Miriam which gave me hope that I'd turn things around like I had never been able to do before. "Now I need to tell you about where to find everything you might need in the apartment." Miriam showed me where the utensils, plates and cups were in the kitchen, explained the system in the cupboard, gave me a key, discussed my chores, her work schedule and general information about getting the mail and doing the laundry. Some nights she would have company come over and I would always be welcome to join in. During the day I would be free to roam around Columbia and do whatever else I needed to do. It was going to be a great summer for both of us. When we were done, I went back to my bedroom. I opened the drawer with Penelope's bras and panties and looked at my white tee shirts and jockey shorts on one side and her mostly pink underwear on the other. I had the distinct impression that from Miriam's point of view it was just some clothes in the drawer and there was no special significance or importance to that fact. That her niece's clothes filled up my imagination with many fun games I could play with them, that possibility was not on her radar screen. Yet that seeming fact was hard to grasp. Was it truly possible that she didn't think that a bra had any significance for me? I decided that it was probably best just to not over think the situation. If I let Miriam know that I was reacting to the bras, she'd probably feel like she needed to move the clothing to another room. So, I prepared myself to always be as cool as a cucumber whenever the topic of my room came up again. I would be totally blas? and help squelch any suspicion that Miriam might acquire as to my excitement of having so many wonderful girl's clothes at my disposal. The thought that I should at least take a good look at a bra and panty to see if they fit me would not leave my mind. Clearly, it would be terribly wrong of me to touch any of Penelope's clothes and what would happen if Miriam caught me at it? She'd be very disappointed in me and embarrassed that she had put me in her niece's room. Somehow, I would have to learn to shut out the temptation. Of course, the easiest way to dismiss the whole idea of trying on the clothes was to discover that they don't fit me. So, I definitely had a good reason for touching the clothes. I picked up a bra and panty from the drawer and went into my bathroom to take a good look at them. First, I looked at the bra, which was made of a pretty pink lace. Holding it by its ends I saw instantly that it would probably fit me. I looked at the tag and it was 36C. My mom was a 38D and her bras were always kind of loose on me. I always had to use the tightest of the clips in the back. This bra would no doubt fit me perfectly. I looked now at the panty which was also pink but of a kind of shiny fabric. I noticed a small bow at the front of the waist band. It was a size six and it was also going to fit me. Now all of a sudden, I felt that danger lurked in my bedroom. Somehow, I'd have to summon up the strength of character to resist wearing the underwear. But I also wondered if I'd ever be able to resist. The siren song was overwhelming me. I put back the bra and panty and closed the dresser drawer. This showed some self-control. A good first step, I congratulated myself. I had more than enough to occupy myself this summer without also getting involved with Penelope's clothes. **** Miriam and I had tuna sandwiches for lunch and then Miriam left to take care of some errands, so I was free to do whatever I wanted to do. Rather than stay alone in the apartment and be tempted by her niece's clothes I spent the afternoon exploring the streets in her neighborhood. When I came back home Miriam was still out. I went into my bedroom and lay on the bed and then got up and sat down in the living room. As long as I lay on the bed, I couldn't help but think of wanting to explore the room, and I had had enough of that frustration for one day. **** When Miriam returned from her errands at six O'clock she was carrying a pizza from Sam's Pizza which was around the corner from the apartment. I was starving and delighted at the surprise of getting a dinner that my mom would not likely ever serve to our family. It was strange having dinner alone with Miriam. As soon as I bit into the pizza, I realized that it was very good. Much better than any pizza I had had before and I exclaimed, "This is so good! This is the best pizza I've ever had!" Miriam laughed and said, "I thought you'd like a quick introduction to the city and all it has to offer!" We continued our conversation from earlier in the day and then I helped Miriam clean up the dishes and take out the trash. When we were done with our chores Miriam said, "Perhaps you want to wash up, take a shower or bath? Then we can get comfortable and watch a show. How's that?" "Great." "Good, it'll be fun to hang out with you," Miriam said laughing. I went to my bedroom and took a shower. After I dried myself off and went to fetch my pajamas, I realized that I had forgotten to pack them. I must have left them on my bed at home. I wrapped the large pink bath towel around me and went to seek Miriam. I found her getting something from a hall closet. She did a double take seeing me in the towel and I said "I have a small problem Aunt Miriam. I've forgotten to pack my pajamas. Do you think there is a store nearby where I could buy some?" Miriam laughed and said, "I'm afraid it's too late for any clothing stores to be open, besides the fact that you've already showered and there aren't any close by. What about sleeping in a tee shirt, did you think of that?" "No, I didn't. I guess I could try that." "But you don't sound very happy about that." "No, it's just that they're kind of confining and I like to sleep with loose pajamas..." "Then what about sleeping au natural?" "You mean ..." "Yes. Lots of people do it." I had never thought about sleeping naked. My whole life I always had been wearing pajamas. Seeing my consternation, Miriam suddenly laughed and said, "Of course, Penelope has some pajamas that probably will fit you. You could wear them. I'm sure she won't mind." My face must have gone beet red since Miriam said, "I apologize if I've hurt your feelings. I wasn't intending to," Miriam said somewhat distraught, "I'm sorry." "Hurt my feelings?" I asked not understanding what she meant. "You might think I'm implying that you're less of a man because you would be willing to wear my niece's PJs." "Oh, I didn't take it like that, Aunt Miriam." "I'm relieved Martin. Some boys might be a bit insecure about their manhood and they could read into my offer things which are not there. It's just a practical thing Martin. Her PJ's are loose and comfortable, will serve the purpose and I would not give it a second thought if you wore them." "They're just regular girl's pajamas?" I envisioned pajamas very much like my own but perhaps with some pink in them, or perhaps a print with little Barbie's all over them. Functionally they'd probably be the same as my regular pajamas. "Yes, they're like the pajamas many girls wear." "I guess I really don't have any reason not to wear them, as long as Penelope wouldn't mind." "I'm sure she wouldn't. I'll show you where they are." I followed Miriam into my bedroom where she said, "They're in the lower dresser drawer." She opened the lowest dresser drawer and neatly stacked inside were the pajamas she had in mind. She took out a set of girls pajamas made of a gauzy pink see-through material, consisting of a very cute loose-fitting pink pajama bottom with an elastic waistband and a pretty pink sleeveless top with gathered pleats and ribbons sewn onto the shoulders. She handed the pajamas to me and at that moment the phone rang in the living room. Miriam turned to leave to get the phone and she said, "Whatever you decide Martin is fine with me. There are a few more pairs in the drawer. You can wear any ones you like." Left alone in the room holding the pretty pajamas I stood frozen in place. I felt myself turning scarlet with embarrassment. They weren't anything like the cotton pajamas I had visualized. These were clearly feminine. I should have known from everything else in the room that they would be like this. By wearing these pajamas, I could pretend to be Martin's girlfriend who's on a visit to him in New York. Martin's aunt would be putting me up in her niece's room while Martin stayed in the other guest bedroom. It made sense to have me stay in the girl's bedroom since I was a girl after all. The power of this developing fantasy led me to see the inevitability of the fact that I'd be wearing the pajamas. I would never have enough willpower to resist wearing such sweet, pretty clothes. It also occurred to me that the more I resisted wearing the pajamas, the more Miriam would think I was threatened by them, and thus actually did want to wear them. So, wearing them was the best way to make Miriam think that I didn't want to wear them. I undressed and found myself trembling in anticipation of wearing the pajamas. They were much prettier than the kinds of clothes my mom wore and much closer to what I would want to wear if I was Martin's girlfriend. My mom didn't have too much pink and certainly not the lacy bow details. When I was naked, I stepped into the pajama bottoms and realized that the material was kind of thin and did not fully hide my penis, which was itself getting excited. I'd have to do something to hide it; Martin's girlfriend simply did not have a penis. I fetched a clean pair of my jockey shorts and put them on underneath the pajama bottoms, which did a reasonable job of hiding my partial erection, though there was a small bulge that persisted. If I was lucky Miriam wouldn't notice it. Maybe she would just think it was normal for boys wearing pajamas. I put on the pajama top and went to the mirror in the bathroom to look at myself and was surprised at how feminine I looked. I felt pretty and feminine and definitely like Martin's girlfriend. In fact, it was clear now that all my past attempts at being Martin's girlfriend never quite turned out the way I had hoped because I was wearing my mom's underwear and dresses. The girlish boy in the mirror I was seeing right now was much more feminine than I had been before in my mother's clothes. Martin would be thrilled to have her as his girlfriend. I realized that I would have to work hard to hide my happiness and excitement in wearing the pajamas lest Miriam think I liked looking like a girl. This was going to be a lot harder than I imagined it would, since I felt a strong desire to let go of Martin and just pretend that I was his girlfriend. If Miriam got suspicious, then I'd have a hard time explaining what was going on. In any event my first order of business was to concentrate on relaxing my penis so the bump would go down. By distracting myself from thinking about the PJ's it went down enough so that I could risk returning to Miriam, and hopefully find out that she really didn't mind my wearing the pajamas. I encountered Miriam in the hallway. She had just hung up the phone and was heading to my bedroom to check up on how I was doing. Anxiously I looked at her waiting for her to tell me to take off the girls pajamas, but she said, "They fit you fine. Are they comfortable?" "Yes, they're not tight or too loose." "Good. My niece is pretty close to your size. She's thin like you, but a bit tall for a girl." If Miriam saw my bulge, she didn't give any indication that it was important to comment upon. Somehow, I seemed to have gotten past the dangers I had imagined. It appears that Miriam really didn't see my wearing girls pajamas as provocative or a cause for worry about my sexuality. They were just pajamas as far as she was concerned. For me, although I couldn't allow myself to show it, I felt that I truly was Martin's girlfriend who for some reason was visiting his Aunt Miriam in New York City. In fact, she was having such a good time with Miriam that she didn't really want to go back to being Martin anytime soon. It was liberating to be feeling so content and happy as I did knowing I had the freedom to wear such pretty pink pajamas without a constant fear that I'd be caught. "I'll slip into something more comfortable and join you soon," Miriam said, and I took a seat in the living room waiting for her. **** When Miriam came back, she was wearing a sheer grayish blue nightgown. It had some lace trim on it and was somewhat low cut revealing the smooth skin at the tops of her breasts, as well as a deep gap between them. I'm pretty sure that I have never in my life been so close to a woman so beautiful and so tantalizingly sexy as Miriam appeared to me. With only the greatest effort could I not become fixated on staring at her bulging chest and the hint of what was inside her gown. On top of that, I became acutely aware of the fact that she was wearing relatively dark colors while I was the one wearing feminine pink colors with lace and ribbons. The only way to avoid feeling conspicuously like a boy wearing girls clothes, was to immerse myself in the fantasy that I was Martin's girlfriend. With that frame of mind, I found myself relaxing since it provided an explanation as to why I was dressed as pretty as I was. "Let's find a nice show to watch on television," Miriam said, "but first I need a martini and you can help yourself to whatever you'd like to drink in the fridge." While Miriam got up to fix herself a martini, I looked inside the fridge and took out an Orangina and then poured it into a glass. I waited for Miriam to fix her drink before sitting down and when she sat down on the sofa, I self-consciously sat down a few feet away from her. Miriam gazed at me with a curious look and I smiled at her and she smiled back at me. I suddenly realized that that I must have been walking across the room and sitting down in my pretend girl persona and Miriam had seen it. I had fallen into it unconsciously because of how feminine the pajamas made me feel. I would have to remember to act like Martin in front of Miriam, even if inside I was his girlfriend. "So how is this Martin?" Miriam said. "Comfy?" "Oh, yes, Aunt Miriam, I think this is neat." To anyone looking in, I was sure that I'd be mistaken for a young woman, either Martin's girlfriend or perhaps even Miriam's niece. Aunt and niece being cozy on the sofa together, but a voluptuous aunt that was for sure. I was unable to ignore Miriam's curves. Her large breasts pushed out the front of her night gown and she had a graceful torso and thighs. Her blonde hair spread out on her shoulders. Her fingers and toes were well manicured. Miriam said, "Let's find a show to watch." Using a remote she found an episode of the "Gilmore Girls" and we watched it together. Halfway into the show, Miriam clicked the pause button. "I'm going to make another martini. Can I get you some more Orangina?" "Sure, thank you Aunt Miriam." Miriam got up and made the drinks and then returned handing me the Orangina. She sat down a little bit closer to me than she had been before, and I shivered with a jolt of excitement. As much as I felt like Martin's girlfriend, I obviously still felt a lot like Martin. At the conclusion of the show, we agreed that it was time to go to bed. The next day was Monday, a work day, and Miriam said she would leave for work about eight in the morning and be back for dinner between five and six. I told her that I had an appointment to meet Professor Oppenheim at Columbia, and otherwise I would spend my day getting familiar with the campus. We said good night and I thanked Miriam for all she had done for me. **** The next morning, I awoke before Miriam left for work. It took me a second to remember where I was and then my memories from the previous day and evening crossed my mind. I stood up and took another look at myself in the mirror. The pajamas were even prettier than I had remembered them being. After washing up I went to the kitchen to get myself breakfast. Miriam was nowhere in sight and then I heard her moving about in her bedroom. I made up a bowl of cereal and while I was having breakfast, Miriam stopped to ask me how everything was, and I told her I had had a great night of sleep. "I'm heading out to work now," Miriam said, "oh, and I was thinking that I can buy you some pajamas on my way home from work today." Taken by surprise, my face reflexively formed a pained look as if I had been hit in the stomach or had stubbed my toe. Miriam must have seen my expression since she said, "What's the matter Martin. You look so pained." "No, I just, um, nothing, Aunt Miriam." Miriam continued to look at me quizzically and then said, "You don't want me to buy pajamas, do you? Do you want to buy them yourself?" While I should have jumped at the lifeline, she was tossing me, instead I said with lack of enthusiasm, "Oh, yeah, I guess I can buy them myself." I saw a sudden smile cross Miriam's face and then she said, "You don't want new pajamas, do you? You want to wear these pajamas?" Never being a good liar, I tried to stammer out a denial, "Oh, no, no, Aunt Miriam, I was just thinking that there was no need to spend the money." I saw Miriam shake her head slowly and then she said, "It's okay Martin if you want to continue wearing Penelope's pajamas. Seriously." It was clear I had been found out. Miriam would put two and two together: my feminine way of walking the previous night, the womanly way I had sat down, and now my obvious dislike of giving up her niece's pajamas. I wondered if I could undo this by suddenly rushing to my room, taking off the pajamas and swearing up and down to Miriam that I didn't want to continue wearing them. But I was sure she wouldn't believe me even if I could pull off the scene. Finally, I said, "Yeah, I guess I like how comfortable the pajamas are." "I know Martin. The material is so soft," Miriam said. "Yeah, they're softer and more comfortable than my regular pajamas," I said. So, this was a good line I figured. Comfort was the most important thing and perhaps just to help me save face Miriam was going to go along with that. "Well great," Miriam said. "You're more than welcome to wear Penelope's pajamas this summer." "Thank you, Aunt Miriam." "I hope your day goes well with Professor Oppenheim. I want to hear all about it tonight. OK?" "For sure Aunt Miriam, I'll tell you everything." **** I had the sense from Professor Oppenheim that he didn't expect too much from me. If I could just learn a little bit of math and take some baby steps into research this summer, then he'd be happy. He described the nature of the problem I was to work on. It concerned some preliminary ideas that might possibly, though it wasn't guaranteed, help in the proof of a very difficult and famous Harry's conjecture that mathematicians had been fruitlessly working on for decades. Professor Oppenheim himself had been thinking about the famous problem off and on for twenty years starting from when he was a graduate student. I wondered if he seriously thought I could make any useful contribution. It was hard to tell from his demeanor. In any event, it was to be a low-pressure summer for me. In addition, Professor Oppenheim mentioned that he'd be taking a few trips during the summer so I shouldn't exactly expect to see much of him. All in all, it looked like I would have plenty of time to explore mathematics at my own pace. I'd work as hard as I could during the day on mathematics and I'd be free each night and weekend to enjoy life in New York City and to get to know Aunt Miriam better. **** For my second evening with Miriam she suggested that we watch another show in the living room after we had showered and gotten into more comfortable clothing. It was a nice tradition, the idea of leaving behind the workday to be totally relaxed, clean and feeling good. Unlike the previous evening, this time I knew at the outset that I'd have pretty pajamas to put on. Even better, the pajamas meant that at least on the inside I would get to be Martin's girlfriend for the entire evening. While my imagination had me comfortably dressing in the girl pajamas, the reality that I'd be consciously wearing them in front of Miriam without the excuse of the previous evening made me self-conscious. It was clear that I really liked wearing them, in fact I preferred them to boy pajamas. And of course, my flimsy argument that they were more comfortable than boy pajamas Miriam could easily see right through. Nonetheless, I couldn't see how I would not take advantage of the chance to dress like Martin's girlfriend, so I just gritted my teeth and headed out to the living room trying to act as blas? as possible. When I got there, I saw that Miriam was already seated on the sofa wearing a nightgown, the same one she wore the night before. "Well, well, well," Miriam said smiling, and I saw her eyes carefully looking at my pajamas. "Besides the fact they look very comfortable, I do have to say that you do look very cute in those pajamas, Martin." I blushed terribly and sat down somewhat coyly next to Miriam. She laughed more heartily and said, "I'm embarrassing you, aren't I?" "A little," I said smiling. "I'll bet it's because you do sort of like wearing my niece's pajamas don't you? And not just because they're comfortable?" Miriam said. Suddenly getting serious I said, "I'm sorry Aunt Miriam." "It's OK, Martin. You don't have to feel sorry." We looked at each other and I felt absolutely naked and vulnerable. Miriam had found a window into my most private and guarded feelings. I felt faint and hot and that my whole future was in Miriam's hands. As if reading my mind Miriam said, "I think I've found out your secret Martin." I felt some tears welling up in my eyes and then a couple of them raced down my cheek. Miriam scooted over and held me and then I began sobbing. "Poor Martin," Miriam said. "You like being pretty, don't you? I should have sensed that right from the beginning." "I'm sorry Aunt Miriam, are you going to tell my mom?" "Oh, pshaw, Martin, why would I do that? Besides, your mom asked me to help you feel more comfortable around girls, so..." "She did?" I interrupted. "Martin, it's OK. She and your dad have been concerned about your feeling isolated from girls. It's painful for a parent to see their children struggling." I collected my composure and sat back up and Miriam released me from her affectionate grasp. "I've wanted so very much to have a girlfriend, but ..." I suddenly felt a rush of tears coming and stopped. It was an amazingly difficult subject to talk about. "But you've skipped two grades and you've always been surrounded by girls that are older than you and not looking to date a younger boy. Am I right?" I nodded my head and not wanting to sound self-piteous I held back from saying that girls probably just didn't like someone like me. Instead I said, "I hope that is all there is to it." I realized at that moment that the elephant in the room was the fact that Miriam knew that I liked wearing the pretty pajamas and that I liked feeling pretty. Surely my having such feelings must complicate the likelihood that I could get a girlfriend. Seeing the angst in my face, Miriam said, "Am I right in thinking that you're blaming your wanting to feel pretty as one of the reasons why you don't have a girlfriend?" Hearing my thoughts vocalized made me want to cry again. Miriam reached toward me as if to hold me again and I said, "I'll make your shoulder wet, or wetter." Miriam laughed out loud, and then I laughed through the few tears that were trying to fill my eyes. Miriam leaned back and then looked at me and said, "You're so funny Martin." "Why would a girl not freak out if she knew how I feel?" "I'm not freaking out." "But you're a woman, and..." "Granted, I can imagine that some young girls might not understand you, but I'll bet that there are many that would like you for who you are, including the part of you that likes feeling pretty. The main thing is that if you like yourself, other people will like you too. If you walk around feeling ashamed, people will believe you have something to be ashamed of and they will shy away from you." "But I am ashamed of myself, I think." "Tell me what you are ashamed of." "That I, ..., that I, ...," I froze unable to say anything. "Tell me Martin." "I'm ashamed that I like wearing these pajamas and that I like feeling pretty. I mean I wanted to wear them as soon as I saw them, but then I was also ashamed of myself. And then I was ashamed of the fact that I took advantage of your kindness in even saying that you didn't mind if I wore them. I felt like I was being dishonest, and you've been so good to me and you don't deserve to be treated like this." "Martin! Enough of that. You have nothing to be ashamed of. You're allowed to be you. Every person on the planet has a right to be themselves so long as they don't take away the rights of others to be themselves. The problem is how young you are, and I must say inexperienced, and there is nothing wrong in that either. As you get older, you'll develop a better perspective. I think its sweet that you like feeling pretty and it doesn't take away from my respect for you." Miriam's speech soothed my worries and I began to relax again. Even though I knew nothing about love, I felt like I must be falling in love with Miriam. At the least I certainly had a crush on her. Later that night, before I went to sleep, I'd make sure to think about what it would be like if she was my girlfriend. Even though that was a silly idea, it seemed like any excuse to think about Miriam would be delicious. There was a pause in our conversation while we each thought over what had been said. Then Miriam said out of the blue, "Have you ever worn your mom's clothes?" My eyes widened and I felt my throat constrict. "Why are you asking me that?" I said hoarsely. "Martin, please don't get upset. Don't you think it's a fair question to ask a boy who likes to feel pretty?" When I didn't say anything, she added, "Wouldn't the thought of doing it cross your mind? I mean, your mom and even your sister have a lot of pretty clothes and they'd offer you a way to feel pretty, wouldn't they?" I wanted to lie and say I hadn't, but Miriam seemed way ahead of me. She was remarkably adept in accurately interpreting the smallest reactions in my face. Finally, Miriam said, "I can see that you have Martin. It?s true isn't it?" "Yes, Aunt Miriam. You won't tell my mom, will you?" "Martin!" Miriam said a bit sternly. "I'm sorry." "I can imagine how scared you are that your parents will find out your secret. It will never be up to me to tell Lillian, but my guess is that someday, when you have a better understanding of yourself, you'll have that conversation with your parents. For right now, I just want to be someone that you can trust to help you grow and get to know yourself better. I think that's what your mom was hoping that I could be for you. The way things have turned out is a bit of a redirection, since your mom thought the main issue in your life was figuring out how to feel comfortable with girls." "But Aunt Miriam," I said excitedly, "not having a girlfriend is why I wanted to wear my mom's clothes." "I don't understand, Martin." "When I first realized that I couldn't get a girlfriend, I figured out that I could pretend to be my own girlfriend. Sort of be both sides of the relationship." "How strange, Martin. And how does that work out for you? Do you talk to yourself?" Miriam said laughing. "Yeah, sort of," I said seriously. "I'm sorry. I didn't mean to make light of what you're saying." "No, I agree with you Aunt Miriam. It is crazy, pretending I'm a girl and acting like I'm a girl dating Martin, but it is the only experience of girls I've been able to have. I hope that things will be different, though I'm not so sure they will ever be." "I don't doubt that you will soon meet a nice girl, in fact, many nice girls on campus." "Yeah, but what girl would want to be my girlfriend knowing I've worn my mom's clothes?" I said. Then added, "And even more, I pretend I am my own girlfriend so when I'm wearing my mom's clothes, I try to act like the way that I think that Martin's girlfriend would act. It's why I like feeling pretty. Really, I think Martin would like to have a feminine girlfriend, so I like to pretend that I'm very feminine. Why would any girl want to date someone who felt that way?" "Don't you think it's a bit strange for you to reach conclusions about how girls think, even though you've never gotten to know any girls?" "So, you think there might be some girls that would like to have a boy pretending to be a girl as their boyfriend?" "Sure, Martin. A better way to think of it is that there are girls that will like you for who you are. If feeling pretty is who you are, then that will be fine, because they like Martin as a whole complete human being." "That sounds great Aunt Miriam. But I suppose if I no longer wore any girl's clothes and stopped wanting to feel pretty, then there would be more girls that might like me." "Perhaps, Martin, but I'd have to say that boys who like to wear their mom's clothes will probably always want to wear their mom's clothes." "But why?" "I'm not an expert on the subject, but from what I've read, it's just the way you're wired. While it?s nice to come up with explanations such as your game of 'dating yourself' to explain it, that is probably just a rationalization for something that is already built into who you are." Once again, I had no answer for what Miriam was saying. Miriam then said, "Answer me honestly Martin. Would you like to wear one of Penelope's bras?" I hesitated and Miriam repeated, "Give me your honest answer." "Yes." "Then go ahead and fetch one of her bras and I'll help you on with it. And while you're at it, get one of her panties too. To tell you the truth I haven't been too happy with you wearing boys underpants underneath the pretty pajamas. That's a fashion faux pas that needs to be fixed." I gazed at Miriam in wonder. Could I have heard her correctly? "You mean I can wear a bra?" "As long as you want to Martin. Do you?" "Yes, I guess I would like to," I said blushing profusely and looking down at the ground. "So, get yourself a bra and panty and I can help you on with the bra, unless you don't need help." "OK." Miriam looked at my embarrassment and said, "Martin, you can look at me. Don't be afraid of the fact that you want to wear a bra. I helped my niece buy all the pretty clothes in your room, so I have a lot of experience with girls who go gaga over fancy pink bras and dresses and everything else. I was never like that growing up, but some girls are and if you're that kind of girl inside, then I understand it and have no problem with it. Be the girl you want to be, and we'll worry later about how that fits in with forming relationships with girls. For you and me, you're a boy who likes wearing bras and I'm your aunt who can provide a bra for you to wear. Just a fact, not a moral judgement." "Thank you, Aunt Miriam." **** I went to my bedroom and opened the drawer containing bras. As tempted as I had been to examine the bras that were there, I had not yet put one on. With Miriam?s' permission I took the top bra off the pile of bras. It was pink and delicate, and I felt a great desire to wear it. Who wouldn't want to wear something so pretty I thought to myself? The panty I selected was also pink, lacy and delicate. It had small ribbons and little ruffles around the leg openings and seemed to match the bra. I felt irresistibly drawn to it. I took off my boys underwear and as I pulled the panty up my legs, I couldn't help but see myself as a girl putting on her panties. This must be how girls feel in the morning when they are getting dressed I thought. Wearing panties was what girls did. The girls in my classes had worn panties and now I was getting to be like them. Didn't this mean that I was somehow sharing their world? The panty passed my hips and then the delicate material crossed my buttocks and now held them with a slight warmth. The feel of the delicate fabric against my private parts caused me no end of excitement, and I returned to Miriam worrying about whether or not I was going to get a boner. Miriam helped me off with my nightie and then helped me on with the bra. "I can see that you have a feminine chest. Your bones are delicate. You're just missing breasts. In fact, I'm pretty sure that I have some breast forms that you could wear with the bra." "Breast forms?" "They'll give you a nice figure. Would you like to have a girl's figure?" I nodded my head and said, "Yes, but how? You mean that I can have breasts?" "They go in your bra Martin. Girls use them to be bigger than they are naturally." "Cool." "I'll get the breast forms." I waited a few minutes until Miriam came back holding a box. She opened it up and I saw that there were two lifelike breasts within it with well-defined erect nipples. Miriam took the breast forms one by one and inserted them in my bra cups. "Whoa!" I said smiling, "they're heavy! But I love them!" Miriam laughed, "They're easily a B cup size and your bra is a large A cup, but they do fit reasonably well." "I don't know, I think they're delightful," I said as I looked down and admired my feminine chest. "You do have the body for them, that's for sure. Put your nightie back on and we'll sit down." When we were settled Miriam asked me, "So is this one of the ways you wanted to pretend to be a girl?" "Yes, Aunt Miriam." I had not been able to take my eyes off the front of my gown where it was pushed out by my breasts. That I was the one who belonged to this pretty scene was slowly seeping its way into my mind. This was not only pretending to be a girl, but it was also feeling like a girl. "So, there you are Martin. Pretty pajamas and a panty and a bra." "Thank you, Aunt Miriam." I hadn't known that such excitement was possible. I felt like I had fallen into a magical land where I could pretend to be a girl as much as I wanted, and every time I looked at myself, I would look like a girl. "You pretty up very nicely Martin." I blushed. Being described as pretty stirred deep feelings within me that surprised me. Yes, I liked being called pretty. Oh, how nice it would be if I really was. We watched another Gilmore Girls, and this time I snuggled up against Miriam, who put her arm over my shoulder and held me. Inches from my face was her bosoms and I had to fight a powerful urge to roll sideways and bury my face in them. The whole time I sat there I could feel boners coming and going. They came when I thought of how pretty I felt, and they left when I got absorbed in the TV show. When the show was over and we were sitting there comfortably Miriam said, "I was just thinking Martin, it must have been very bizarre for you to find yourself in my niece's room. So much temptation!" "I guess so, Aunt Miriam." Miriam laughed and said, "You must have really freaked out having to share a drawer with Penelope's bras and panties." I smiled and said, "I didn't know what to do. I didn't want you to be embarrassed." "You're a very thoughtful young man, Martin." **** The next day after Miriam left for work, I allowed myself the luxury of feeling like I was Martin's girlfriend, only this time I was as feminine as a girl could be. Dressed in my bra, panty and pajamas I imagined myself sitting on the sofa with Martin putting his arm around my shoulder and kissing me. I felt my heart beating fast with anticipation. I tried to imagine what Martin would want to do with my body once he had access and I found myself unable to think of what that would be. Would he touch my body with his hands and if he did, how would he do that? What about our kissing? Is it just a matter of holding his lips against mine, or is there more to kissing than that? Despite my ignorance, my fantasy caused my penis to bulge inside my panties and I had little choice except to relieve myself in the bathroom. I took extra care to make sure that my effluent did not land on my panties or pajamas. **** A few days later, during the afternoon, Miriam got a call from Lillian at work. This was highly unusual, but Lillian said that she purposefully wanted to talk to Miriam without Martin being around. "What's up?" Miriam said showing some concern. "No emergency," Lillian said, "I just wanted to find out how things are really going with Martin." "Very nicely." "To be honest. Martin's father and I are somewhat surprised at how easy his adjustment has been. We were worried that his shyness around girls and women might make you regret taking him in." "He is shy, Lillian, but we got past that pretty well. We had some nice heart to heart conversations which seemed to open him up and take away some of his fears. He knows remarkably little about girls and I have tried to gently ease him away from some of his misconceptions." "Oh, God, Miriam, that is so great. What are some of those?" "Well, for example, he makes blanket assumptions about the way all girls think, yet he doesn't even know any girls to talk to that might let him know about how girls actually feel. For example, there might be many girls that would like Martin exactly how he is now. Shy and studious." "Yes, we tried to tell him that as much, but he didn't seem to believe us. I guess coming from you he's more trusting." "True." "As I?ve said, his father and I have never discussed the facts of life with him, so we don't know if he knows anything about the opposite sex. He never brought the subject up, and we didn't see the point in telling him about things he wasn't going to be doing." "Well, Martin made it clear to me that he truly doesn't know anything at all. He said that he doesn't know the first thing about how to kiss a girl, let alone anything else about what boys and girls do together." "I wish there was some way you could teach him about these things. Perhaps that's a crazy thought, but you seem to have carved out a unique channel to him that his father and I were never able to establish. Now that he likes you and feels comfortable with you, you could sort of give him some idea of how girls think and what girls and boys do together." "I think that's a great idea Lillian. Your instincts are good. He does listen to what I say, and I think that he is sort of getting a crush on me, like the way you predicted he would." "Really now!" Lillian said laughing. "I shouldn't laugh because he could get hurt, couldn't he?" "At the first opportunity I'll make sure he understands that there is nothing wrong in forming crushes on girls, it?s quite normal behavior. But crushes are often short-lived and a lot different than a reciprocal relationship." "I feel so guilty for putting this all on you, Miriam," Lillian said. "Stop that Lillian," Miriam said. "I'm having a ball with Martin and I'm more than willing to help teach him the kinds of things he should know about so that he'll be successful in love one day." After getting off the phone, Miriam spent quite a bit of time contemplating where things were with Martin. The fact that Martin liked to cross-dress was something his mother had no inkling of, and it would certainly have some effect on the kind of nurturing that Lillian was hoping she could do. Anyway, it was important that Martin be allowed to express himself any way he saw fit, so Miriam decided she had better begin a conversation that would hopefully, in time, prepare Martin for the real world of girls. **** The next evening, when I was together with Miriam on the sofa I said, "I feel so content and happy." "I'm glad that you're happy," Miriam said. "I know I am happy, Aunt Miriam, but I do feel somewhat confused now about whether or not I still want a girlfriend." "What do you mean?" "I guess I mean that you're my friend and you aren't mad at me for pretending I'm a girl, so do I really need a girlfriend?" "Are you saying that I'm your girlfriend?" "Oh, no, Aunt Miriam, I realize that I'm too young to be your boyfriend, but I... but I'm happy just doing what we've been doing so why should I learn how to date girls? It just seems so hard and difficult and then they'll just not like me for who I am anyway." "I'm flattered that you feel like you and I have a special relationship and we do. But it?s just a passing phase for us. You are young and have a wonderful future ahead of you and that will definitely include a girl your own age. You mustn?t lose sight of this future for yourself. It will always be important for you to learn about how to feel comfortable with girls and what boys and girls do with each other." "I guess you're right." "I know I'm right." "Well, can you teach me about girls? Everything I don't know." "What particular thing do you feel like you really want to know about?" "Like how to kiss a girl?" "You don't know how to kiss a girl?" "No, nothing about it. I've never kissed one." "Never been on first base with a girl?" "What do you mean by first base?" Miriam was surprised by the degree of Martin's ignorance. She thought back to her conversations with Lillian. It was clear that job number one was to get Martin up to speed with just the most basic facts of life. While girls might find some innocence in a boy to be charming, wholesale cluelessness would be a turn off. Providing this education to Martin seemed like exactly the kind of thing that Lillian was hoping that she would take on, and it would be kind of fun. "If you don't mind, I think that I need to teach you about first base. For sure the girls you meet will assume that you have some idea of what it is that boys and girls do with each other when there is an attraction. How does that sound?" "Super, Aunt Miriam," I said excitedly. "Good, then tomorrow night, we'll talk about being on first base. Right now, we'll snuggle and watch a show!" End, Part 1.