Girlyboy

byDennis_St_John©

Sitting there looking at myself in the mirror while I touched up my makeup, I wondered what I'd become. The reflection gazing back at me with emerald green eyes was that of fresh faced young woman, 22 years old, dark blond, wavy shoulder length hair, a wide mouth with full pouty red lips, a strong chin and high forehead. A very good-looking young female, some might even say beautiful, but I'm no judge about those sort of things.

She had full upstanding breasts, a slim waist, tight round bottom. Long, well shaped legs and small feet. Standing without heels, she was 5' -- 8" tall and could wear 4" high heels without over topping most men. Not that it mattered when I'm lying down, or on my knees. I saw a slight blush cross that face in the mirror at the thought, feeling my ears get red and marveled that I could still blush even after all this time.

Some might say I should be traumatized by the events that led to this point, but what do they know. I feel I'm well adjusted, and accept what I am now, although at first I didn't, not by a long shot. The repeated application of a leather strap to my bare bottom and thighs cured me of any illusion I had in that respect, and to tell the truth an enormous relief once I accepted it.

I didn't start out life as a female, and even now, I'm not truly one. At eighteen, I was a rather frightened young man, and yet I'm not sure at this point what I was frightened of. A lot of things I guess. At that time I was a slim, bordering on skinny, young man with a soft rather indifferent face, neither masculine nor feminine, something half way between the two. I had little or no hair on my body to speak of and a rather small penis, as I was so often reminded by the other guys in the showers at school.

Some would say I had a weak face, or maybe an effeminate, whatever that meant, so I got picked on a lot by bigger, older, or stronger boys. Being constantly bullied was one of the things I was frightened of. If there was a particularly nasty practical joke going around I was one of the first on the receiving end. The shower after gym class frightened me, having to strip naked and shower with all those older and stronger boy was very intimidating. I couldn't help looking at their manhood through the steamy air, wondering why mine was so small compared to theirs.

A few of the boys would get very nasty if they caught me looking at them, grabbing their cock and pretending to jack off, waving it at me and asking if I wanted some. More than once the shower water hid my tears of humiliation as I turned to stare at the wall, hearing the ugly laughter behind me.

Gym classes and sports also frightened me, and gave me a feeling of worthlessness. When they picked sides for some game or other, they never picked me, unless the teacher assigned me to a team, or they were one short and needed the extra body. Even then, they never accepted me willing, usually adding nasty comments in a low voice so the gym teacher didn't hear, like ...'here comes the wimp'... or ...'we got stuck with the fucking sissy fag again'...

Also, I never was any good at sports. I couldn't run fast enough, couldn't catch the ball, missed the goal all the time, fell down or tripped over my own feet, so a lot of it was my fault that no one wanted me on their team. Add to that, I was an indifferent student, usually ending up bottom of my class, consistently, year after year.

It's not that I'm dumb, just disinterested and bored in class. On the other hand I was an insatiable reader, staying up long into the night with some book or other, usually adventure books with big strong hero type, but not the ones that did me any good in class. This habit also made me later for class a lot, and hard to stay awake and pay attention, adding to my overall poor performance.

In the cafeteria or the library, I'd find a place to sit by myself in some corner, safe in my self-imposed solitude and loneliness. I had few friends in or out of school, learning early not to trust my supposed school friends, having been the butt of too many nasty jokes and comments for some of the things I'd said or done that I thought my 'friend' would keep secret. I was smart enough to keep one thing secret from everyone, including my grandmother who I lived with. My parents died in a car crash when I was six or so, and I don't remember much about them. My grandmother was a widow, but agreed with the authorities to take my in after the accident. As I turned out, I have no other living relatives, so it was either live with her, or the orphanage, but I didn't know that at the time.

She was nice to me, but a little forgetful sometimes. Not that I was neglected, I wasn't, but several times she did really odd things, like buying me a whole packet of girls panties, or asking me if I was ready to start wearing a bra. At the time, I just thanked her and stuffed them in the back of a draw, not wanting to upset her. Another time she brought me a dress and kept muttering about how nice I'd look in it. That time I reminded her that I was a boy, not a girl. She seemed a little surprised, then laughed, and patted my hand as she said sorry.

"You should think about getting your hair cut, you know. People will mistake you for a girl with it long like that." I told her I get it cut soon, and promptly forgot about it.

A lot of the guys were wearing their hair long, not the jocks, but the other's, the ones I thought of as 'normal', like the guys in the computer or chess club, or the ones that went in for the school drama class. If I could pick at point where it all started, I would have to say it was after my one and only date with a girl, but not just any girl. I heard the guys at school talking about this one particular girl.

The word slut and whore were tossed about, and how easy she was, but not knowing much about sex at that time, I really didn't know what a guy was supposed to do. That wasn't to say that I hadn't tried to go out with girls, I had, but none of the ones I asked wanted to go out with me. That was cause for a lot of teenage frustration, and the nasty habit of jacking off.

My imagination was filled with what I supposed went on when you 'went' with a girl, all wrong as it turned out. I had a hard time getting passed their breast. I could imagine feeling them, even kissing them, as they were the most prominent feature of any female. It was below the waist that I had a hard time imagining. That part was just a fuzzy picture in my mind with no distinct shape, size, or position. Or what you actually did when you got there. The few pictures I'd seen of men and woman 'doing it' didn't really show what they were actually doing. A lot of the fault rested with the level of sex education in the schools at that time, which was little or none, depending on the year and age of the students.

I did manage to get a date with the girl in question, and I took her for a meal at Burger King, then a movie. To my surprise, the moment the movie started she took my hand and slipped it inside her coat over her breast. Much encouraged I played and fondled her breast to my heart's content, and was bold enough to unbutton her blouse and put my hand inside. She didn't object, and I soon had her bra open and touching bare skin. It was intoxicating, and we were both content to do that until the forgotten movie ended.

With no car, or a place to go, we ended up in a small wooded area near her house where we proceeded to start kissing and fondling each other. Having got to her breast before, It didn't take me long to open her coat, blouse and bra, at which point she draw my head down to her nipples and told me to kiss them. I did, and it wasn't long before I had a nipple in my mouth and I was sucking on it. She moaned a lot and her body moved in odd ways as she kept rubbing her thighs together. This led me to get a little bolder and I soon had her skirt up and my hand between her warm silken thighs. She was wet and warm, so I supposed this was natural. My next goal was to get her panties off, and that was easier than I expected.

They were over her slim hips and slithering down her legs in nothing flat, and like a gentleman, I knelt down and helped her step out of them. As soon as I knelt down, she took my head and pulled it towards her pussy, and I just wished the light were better so I could see what a pussy looked like up close. All I saw was a darker patch of shadow, and smelled her perfume. It was intoxicating, but I had no idea what she wanted me to do.

In the end, I just placed a kiss on her lower tummy and stood up. Her panties went into my pocket with no thought of keeping them, just putting them somewhere I could find them when she needed them. After standing, she reached down and unzipped my pants, and I gasped with surprise and pleasure as she took it out and squeezed it. She smiled at me, giggling softly, turning me around so I had my back to the tree then knelt down in front of me.

The next sensation was almost impossible to describe as she took my hard cock in her wet, warm mouth and started to suck me. The sensation was almost indescribable and I felt, well I'm not sure what I felt, but the feeling kept growing until I thought I'd explode. Then she stopped and stood up, shooshing me as she stood close.

It was then I realized I was moaning loudly, and that someone was coming towards us, two someone's by the sound of the footsteps and voices. We faded into the deeper shadows, but whoever it was stopped a short distance from us. Peeking around the tree, she pulled her head back quickly and murmured 'Cops' in my ear.

That immediately put a damper on my ardor, and we careful made our way through the tree in the opposite direction. After that, it was downhill all the way. With nowhere else to go, and the lateness of the evening, she said she needed to be home shortly. I walked her home, and after one last kiss, she went in.

I think I almost ran home, wanting to get into bed as quickly as possible and relive the events, and the possibility of what might have happened if we hadn't been interrupted. That was satisfying in a way, but not as good as the real thing, but I was never to know. Her panties fascinated me, and after a wash gave me many hours of erotic pleasure.

The black lace felt so good around my cock, or just laying across my face as I relived the encounter. I did try to date her again, but having got her home late, she told me that her parents wouldn't let her go out with me again. Acute disappointed drove me nuts, as I doubted I'd find another girl like her any time soon.

Then I made what I can only describe as the fatal mistake. One evening when I was feeling particularly horny, I decided to put her panties on. It was fantastic to feel them slid up my legs and over my slim hips, settling them round my cock and balls, almost like a hand caressing me. It didn't take long before I was prancing and swishing around my room in them, looking at myself in the mirror and pretending to be a sissy queerboy, all limp wristed and lispy. That made me even harder and the front of the panties stick out.

It felt dirty and erotic at the same time. Kneeling down in front of the full-length mirror I slowly jacked off, telling myself what a filthy little pervert I was doing this. That sent a shiver running up my spine. I was a dirty little panty-wearing pervert and I could almost imagine myself sucking cock like a proper fag.

It didn't take long to cum, hearing myself say that, and I had the most fantastic climax of my life that evening. I slept like a baby but the next morning I felt so ashamed of myself for doing it and swore never do it again. I did wash the panties out and tucked them away in the back of my underwear draw after fighting with myself about keeping them or throwing them away. I lost and kept them.

That lasted all of two week before I pulled them out from their hiding place and slipped into them again. Having my own room meant that I could do pretty much as I pleased, as my grandmother couldn't get up the stairs very well. Her bedroom was on the ground floor, so walking around naked, or even with just a pair of panties on didn't seem that much of a risk. Just after I started wearing them regularly in the evening, I remember the packet of panties my grandmother brought for me, and retrieved them from the depth of my closet. It was so much fun to wear them, wondering if my grandmother knew I was really a panty wearing sissy boy at heart.

I even went as far as wearing them under my clothes to school several times, but only on day that I knew we didn't have gym class. That was a kick, sitting in class wearing girl panties and looking at all those oh so macho guys around me. If only they knew. It also made me wonder how many of them might be wearing panties as well.

That was when I met Steve, the boy next door, a guy really. He was a little older than me and he and his parents had moving in about six months before. I didn't see much of his Mom and Dad, as they always seemed to be flying off to somewhere or another on business, leaving him home alone much of the time. Steve worked at an electronics store down town, but I'd see him from my bedroom window out by the pool, sun bathing, exercising or swimming.

I'd even seen him swimming naked a few times, as I knew when he climbed out and stood there drying himself off. He was well built, but not overly muscular, with dark hair and a strong face. He was hung, as they say, and it made me feel a little uneasy that my male equipment wasn't anywhere near as big as his. What surprised me the most was that he had no pubic hair. That seemed to make his cock look bigger somehow, but I was puzzled why he had no hair down there. Was it natural, or did he remove it, like shave himself clean. Our house didn't have a pool, so it was inevitable that he'd invite me over for a swim one very hot summer day. At first, I incline to decline his offer, as like most macho type guy he tended to intimidate me a little. He was kind and a little persistent until I finally agreed to come over. Grandma was sitting in her favorite chair in front of the TV, the room AC going full blast, so she wasn't about to move. I told her I was going next door and grabbing my towel, swim suit, and hopped over the back fence.

I guess I was a little scared at first, but what of I couldn't say, just that I was. After I changed in the cabana, we went for a swim and talked about this and that while his Mother laid out food snacks, chips, and drinks for us.

That put me at ease, and I was soon lounging next to him by the pool. Later, his parents took off to some party or other, saying they wouldn't be back till late. I could see where Steve got his good looks from; his Dad was a tall, good-looking man with salt and pepper hair and a lean, muscular body.

His Mother on the other hand was a beautiful petite woman, and only a little shorter than me. Steve waved to them as the left, and I murmured a thank you and waved as well. The moment he heard their car pull out of the driveway, Steven pulled off his bathing truck and jumped into the pool, laughing at the expression on my face as he swam back and forth.

"Come on, the water feels great."

"I've never been swimming without a bathing suit."

"You should try it, it feels wonderful." He laughed again. "Come on, there's no one here now expect us now. You shy or something?" He teased.

"But what if your parents come back?"

"They won't. They won't be back until morning, anyway."

"Oh?"

"Yeah, their off to a swingers party."

"Swingers?"

"Yeah, you know, wife swapping and all that." I didn't know, but wasn't about to say so.

Reluctantly I took my bathing suit off, looking around at the other houses and the fences to see if anyone was looking. Of course, no one was, so I slid into the water after some hesitation, feeling it flow around me in a way I'd never felt before.

He was right; it did feel wonderful, and sort of forbidden at the same time. I guess I couldn't help myself, and I started to get hard. If Steve noticed he didn't say anything, but I did notice he was larger when he got out of the pool and dried off. I did the same, and we lay there for a while sunbathing in the nude. I also explained why he didn't have any tan lines.

"Hay! You're getting sunburned."

I started to turn over to sit up, but he pushed me back down and poured suntan lotion on my back. I'm not sure what I felt as his hand touched me, but he chatted on about this and that as he worked the lotion over my back and shoulder, then my legs and butt. That felt strange, having a man rub suntan lotion all over me, definitely erotic and somehow sexual, feeling myself starting to get a hard on.

"Turn over so I can do the front."

"I can do it." I said quickly, not wanting him to see my erection.

"Okay, but my hands are all ready covered in lotion."

"That's Okay."

"Well if you are going to do that, you can put some on my back then." He lay face down on the chase lounge and held out the bottle for me. I took it, not sure what to do. Thankfully his head was turned the other way so he couldn't see how aroused I was.

Reluctantly I poured some on his back and began spreading it over his well-muscled body, his skin feeling warm and hard under my hand. I only spread it over his back and legs, as I wasn't about to touch his butt. He didn't seem to mind and made no comments when I skipped that part of his body.

After spreading some over the front of my body and putting a towel over my middle, we lay there in silence for a while. I kept eyeing his body from behind the safety of my sunglasses marveling that not only was his pubic area hairless, his whole body was. His was so unlike the jocks at school, all hairy and Neanderthal. By comparison, he was a Greek god. I was betting the girls at his school went nuts over a guy like this. By two o'clock, the sun was getting a little intense, and we were both sweating, despite the occasional swim. In the end, Steve sat up and wiped his face.

"Fuck! It's hot out here. Let's go indoors in the cool."

"Okay," I started to reach for my bathing suit, but Steve shook his head.

"You don't need that, and besides, we have to take a shower before we can sit down. Don't want to get suntan lotion all over the furniture.

I gulped, as I thought he meant take a shower together, but he pointed out a shower in the spare guest room and headed off down the hallway to his room. Showered and feeling squeaky clean again I wrapped the towel around my wait and walked back into the living room. Steve was all ready there, sitting on the couch naked with a glass of lemonade in his hand.

He pointed to a second glass on the coffee table and motioned me over. The air was cool and crisp, just perfect after the hot sun. I sat down beside him and sipped the lemonade. It was cold and not too sweet, and I gulped half the glass quickly.

Steve finished his and went for a refill, coming back with a jug and refilled mine. We sat there chatting for a while, I asked about his work, and he asked about school as I worked my way though most of the jug. Oddly, he didn't drink any from the jug, but went into the kitchen to refill his glass. By this time, I was feeling very relaxed and not particularly concerned as my skirt towel rode a little higher. Not that I was exposed, so to speak, but just relaxed enough to not worry about it, or the fact that Steve was sitting beside me in the nude. I guess I should have been, but I wasn't, even when he got up and refilled the lemonade jug. I did take more than one look at his manhood, but if he noticed it, he didn't say anything, at least, not then.

"Hey, you want to watch a porno with me?" He looked at me a moment. "My folks have a great collection." I suppose it was because I was so relaxed for some reason that I said yes, not that I'd ever seen one before, and the idea excited me.

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byDennis_St_John© 5 comments/ 110663 views/ 38 favorites

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