It is natural for me to feel feminine at times. In my childhood and early youth, those feelings blossomed naturally in the presence of girls and women.
I love breasts. I love to lick them, kiss them, hold them. I think they are so beautiful. I love women. I like how they look, and how they talk, and how they think. One Christmas when I was a teenager I worked in Macy's in the women's clothes department. I felt wonderful there all the time, and loved seeing the women looking at clothes and trying things on, and of course I loved looking at their breasts. I looked at how different bras shaped different kinds of breasts, and I imagined the breasts that hid under the clothes women wore.
I don't remember the first time I put on a bra, but I know I did it many times from when I was a small boy. I would almost go into a trance, and feel compelled to put it on. When I was a young boy, I didn't find my attraction for girls and girl's clothes unusual. Obviously girls are attractive, they're in every magazine and commercial. So it seemed natural to like them a whole lot-didn't everyone?
We lived near a Catholic girl's school, and as a young boy I used to gaze jealously at the girls coming and going along the street in their uniforms. On Halloween, I asked my mom if I could dress as a girl, and she put together a costume for me. I felt very good, and I was pretty. Before I go further, I should say that I'm straight, and I like all the things men like, and also that when I was teased for dressing as a girl, I beat up the guys who teased me. Nevertheless, I feel good when I'm soft and feminine, and I remember feeling wonderful (and innocent) dressed as a girl for Halloween.
I remember looking in drawers for my mom's bras, and also my friend's mom's when I was young. Once we found a black lacy bra his mom's drawer, and we both tried it on. I guess I was about ten when I swiped the bra of a busty teenager from the clothesline at our apartment house, tried it on (34C), and then replaced it. I became fixated on her, and wondered what it was like to have big breasts like that. When I visit friends, if there are underclothes lying around I might be overcome with the urge to put them on, secretly.
My brother and I managed to get our babysitter to lift up her top and show her bra, by promising to go to bed right away. Of course, we got so excited, we couldn't possibly get to sleep, and I remember I kept running down the stairs to show her my penis. This was probably a big headache for the babysitter, but the memory excited me for a long time.
I've always thought girls were very pretty in almost everything they do. I remember learning to write, sitting next to a girl in class, and I thought her handwriting was so beautiful, and tried really had to make mine as nice.
My sex life is pretty normal and although I'm going to tell you some experiences I've had that are on the unusual side, the bulk of my sexual experiences are not unusual at all. I like to fuck, and I also like to masturbate like a regular guy. I've had great relationships with women, in part because I like them so much and I'm very sympathetic.
Women turn me on (always), but also I'm turned on by masturbating with other men, or even thinking about it. In fact, I've had almost two parallel sex lives-one, concerned with being a man, with girlfriends and buddies and the other more secret, feminine eroticism that is also deeply compelling. For most of my growing up, one or the other of these has held sway, but they are both with me all the time.
I've had a fascination for bras and breasts and women's bodies from a young age. In grammer school there were few avenues by which I could follow my impulses or fulfill my curiosity. Of course I love the girls and teased them endlessly, but they didn't have bras or breasts or deep secrets. I felt hungry to know more about women. I would ask my mother to take me shopping with her so that I could be in that world. I was always looking at women, their bodies, their hair, their mannerisms. But I could never be close to one, and I felt empty. Happily, my attraction found an object when I was around twelve, and my feelings blossomed....
My friend had an older sister, Dianne, who was around twenty. We would talk when he was not around and I was over to visit after school. My friend joined the baseball team, and so wasn't around much, their parents worked; we were alone in the house. Dianne had a job as a waitress, so in the afternoon she would be getting ready to go out. I started hanging out and talking as she was getting herself ready--in the bathroom doing her makeup, ironing clothes, fixing her hair and like that. I found this really attractive and mesmerizing. I think she liked the attention, too, because she encouraged me to stay around her. She would talk with me about whatever was on her mind, all kinds of things. I found her fascinating.
Pretty soon I was following her around in everything she did around the house. Since I was so young she pretended that it didn't matter if I saw her half-dressed or without makeup, and she used me as a helper, to get clothes from her bedroom, or to hold something for her. I would do anything just to stay in the room and be able to watch her. When she'd try something on, or finish her makeup, she'd ask me if it looked ok, and that made me feel much older and like she cared about my opinion as a man. As I sat in her feminine glow, I also felt pretty, with red lips and a soft body, and I felt innocent and natural.
At first Dianne was pretty modest, but I would catch glances of her breasts under robes and if her blouse wasn't quite buttoned. I was happy and glowing around her, and she relaxed and felt safe with her young helper. Over time, she let go of her modesty, and would walk around in her lingere, and do her makeup in just her bra and panties. Even so, if she was going to take off clothes she tell me not to look, but I always peeked and saw things in the mirror, and she knew I did. She would quick grab a towel naked from the shower, and run half dressed to her bedroom. This was all amazing to me and I felt like I couldn't get enough. It was the center of my life.
One day Dianne was trying to put on a new fancy bra to go out with her boyfriend and she had trouble with the clasp. She struggled, with her arms pulled back (which made her boobs stick out), and then she gave up and let go. Her boobs dangled freely under the loose bra, and I saw everything! Then she asked me to help! Although I went blank I was so nervous, later I remembered that moment many, many times afterward.
Dianne no longer turned away when she put on her bra, and so I regularly glimpsed her breasts. For the first time I saw that nipples could be soft and flat or hard and pointy, and I have vivid memories of how her breasts hung and jiggled and pointed. Twice Dianne cupped her breasts in front of the mirror, and would ask me if I liked them. I was in love, and felt like a man. I was fixated, and melted like a woman.
Dianne would take a shower and then with just a towel around her, shave her legs. I would sit transfixed. One time, when summer was approaching, she spread her thighs apart and shaved her crotch. I'd never gotten so close to seeing a pussy before, (though she still had panties on) and I was awestruck. But compared to her breasts, I didn't think thighs with hair were so beautiful and it was a while before I learned the attractions of a hairy pussy.
A big moment came when she let me follow her into her bedroom to get dressed. I had hardly ever gone there, never with her, only to get clothes for her, and I felt like something special was going to happen. Dianne was just nonchalant and talking, as she usually was, but I was awestruck as she peeled off her clothes-all of them-and then examined herself in the mirror. I was entranced!
Then she turned her back, went to the dresser, and got a fresh pair of panties while I stared at her jiggling ass walking past me-and then she turned and put them on in front of me! It was my first view of her full crotch, and I felt like I'd seen a deep secret. She asked me to get her bra from the bathroom, and when I returned, she was pulling on pantyhose, and her breasts were dangling and jiggling in the air. I sat on the bed while she finished dressing.
When I would get home at night, I had to endure dinner with my parents before shutting my bedroom door and 'doing my homework'. I had begun masturbating regularly a year or so before, with all the usual fantasies and girlie magazines. Watching Dianne made me hot in a different way. Looking at magazines gave me a different thrill, like I possessed the women in the pictures.
With Dianne, I was not a man, I was a boy, and I drank in everything about Dianne's feminity, and it was very, very appealing. I had no thought of 'making it' with her, but at the same time I was very turned on. Alone in my room, I would dream of what I had seen that afternoon, my heart would pound and my penis would begin to throb, and I would rub it until I climaxed. Then at night in bed I would masturbate again, sometimes three or four times.
In masturbation, I would sometimes just casually touch my breasts and feel like they were those of a woman, but then I would go on to my usual fantasies and routines. Once I 'borrowed' one of Dianne's bras, and wore it to bed, under my covers. It seemed very natural, because when I was with her, I often moved like her, and the feeling of my body in my clothes changed. I always felt like a male, but at the same time my mind would drift and I would feel like her, soft, with breasts and long shiny hair, and long lashes. So having her bra only made my feelings 'official'. I didn't think of any of this at the time, though. I was just full of impulses and feelings, and one of the feelings was that I, too, was very feminine.
Dianne grew troubled, and for a few weeks wasn't cheerful, and sometimes was harsh. She apologized, and said it had nothing to do with me. Then she suddenly announced that she was getting married, very quickly (with the help of a shotgun). Our connection ended abruptly.
I had one girlfriend during my time with Dianne, but it didn't last long. Soon, I had my first real girlfriend. She was little and blonde, like an elf. Her breasts were small, but perfectly round. She didn't need to wear a bra, but had one anyway (so small I couldn't fit it on). Her hips were narrow, and her little ass was round and firm. Her name was Adrienne, which I thought was a beautiful name.
She didn't want to have sex, except that she loved to get naked and make out. We didn't really know what to do, and would just kiss and feel and suck however we felt. I loved sucking Adrienne's nipples, and she would suck mine, too. Sometimes I would cum rubbing against her, but I didn't have any sperm yet. It felt really good to be naked with her, to be a boy and a girl, and not very different.
Through most of high school and into college, my feminine feelings were just part of my everyday self, and I had no unusual relationships around them. They receded into the past, as I pursued growing into a man. I had a good sex life, and a steady girlfriend most of the time. When my girlfriend went to Europe, I was alone, and my feelings began to grow again, and I fell into another situation with a woman like Dianne.
Perhaps you have never felt so pretty you wanted to sing. Maybe you never felt your lips were softer than any man's could ever be. Perhaps you would be afraid if you stroked your body and felt it had full hips, and breasts-I was! You might think it is all silly, and just want to read about cocks and cum and hairy balls, and you find my story boring. Well, then, don't read any further.
If you like my story, there's more, much more, coming.