Finding the Real Me

Every "coming of age", exploring sex comes of legal age.

When I was growing up, I thought of myself as different than anyone else. It wasn't until I turned 18 that I realized I was far from alone. Growing up in a one parent home, and being a "runt", as many classmates called me, life wasn't easy. My mom worked hard to provide for us, but, she had a weakness for men, too. Usually bad ones. Every guy that hung around more than a couple of "dates, became "Uncle" Tom, Josh, Don...you get the idea.

Most of them pretty much ignored me. I wasn't a sports guy, so I was pretty invisible. I stayed out of their way, for the most part. After all, they were there to entertain my mom, and vise-versa. Another problem for me was, my mom named me "Truman". Truman! WHO does that? You can't imagine the ribbing I got from that... "True Man? You aren't even a true boy."

We lived in a small house, in a run down neighborhood, and the walls were thin. Even at a young age, I knew that my mom loved the company of men, a lot! As I grew older, and started exploring the internet, I was excited, then shocked, then saddened. These men, with monstrous (to me) cocks were pleasing beautiful women. I knew that my own cock was small, but, I never realized just HOW small. I had always thought that it was just that I was shorter, thinner, than the other guys, and that my cock, like my body, would grow. It didn't, I didn't.

I went on a few dates in my senior year After all, I was 18, and most of the guys in my class had been going on dates long before this.. Even though I was sometimes shorter than my dates, they seemed to like me, always saying I was "cute". Things would go well. We'd get past the kissing stage, I got to feel their breasts, even touched panties, but, when they felt for my cock, it was over. A couple actually laughed. As if the humiliation couldn't get worse, the last girl let it out in school, and that ended my dating.

One friend that I'd had for many years, took pity on me, and was going to teach me about sex. She taught me to pleasure her with my tongue, and was going to suck me, and let me fuck her. The look on her face, when my boxers came down, though, said it all. She very solemnly told me ( after sucking me to my first, and only, blowjob, that there was just not enough there to even get inside her. That look of pity almost killed me.

From that point on, I gave up. I did my school work, but nothing social at all. I lived for the video games after school, they became my world. (And, of course, some internet porn, which, in truth, only frustrated me because I'd never know that joy. I suffered through my education, but, in my senior year, my mom was dating a different kind of "Uncle". Instead of ignoring me, he was kind, and seemed to do more than just tolerate my existence. They had been "dating" about a month, when he would make a point of checking on me, asking about school, and my life in general. One night, I happened to hear him taking to my mom about me. He was telling her it wasn't right for a boy my age to be cooped up in my room, that I needed an outlet, a pathway to socializing in the world. Otherwise, I'd have a difficult time making it in the real world. Mom told him she was worried about me, but didn't know what to do.

Charles (his name, that I forgot to mention) said he was thinking it over, and had come up with something that might help. It was then that their voices went lower, and I was left to wonder. I didn't have to wait too long, though. The next morning, he asked at the breakfast table, if I'd ever been camping, and would I like to go with him. Naturally, I never had done anything like that, and told him I wouldn't know what to do. He told me not to worry, he had all the gear, and I might like it. I won't lie, I had my doubts, but, as I said, he had been nothing but nice to me, so I figured it was worth a shot, even if it would be a one time thing.

The next morning, Mom was shaking me awake. 5:00 in the morning? Was the house on fire? I tried to roll back over, but she reminded me that I'd agreed to go camping. I was regretting that, but got dressed in old clothes that I wouldn't mind getting trashed, if it was muddy. Thirty minutes and 2 cups of coffee later, Charles knocked at the door, and smiled to see me up.

"Come on, Champ, we are burning daylight!"

Mom handed me a thermos of coffee and a bagel, and I picked up my school backpack, that I had put a change of clothes in. We hopped in his pickup, and headed down the road. He kept the conversation light, explaining where we were going, that there would be a great place to swim, and, if I was interested, a good fishing spot. Of course, like camping, I knew zero about fishing. By my phone, I saw we had been gone two hours, but were already turning onto a dirt road, heavily lined by trees. We got out of the truck, and Charles immediately started handing me gear, and pointing to a clearing. "We'll set up here, the lake is just around those rocks. "

His manner was so calming, it was clear he wanted me to feel no pressure. I wasn't much help, but we got the tent up in no time. I was impressed at how well he put things together. I didn't ask, but bet that he'd done this many times. When our gear was stowed away, he pulled out a cooler and said, "I brought plenty of beer. Your Mom doesn't need to know about that though, ok? This is just a guy weekend. Just relax, and unwind, ok?"

I'd never drank beer, and honestly, it didn't taste that good, but, it wasn't awful, either, so I drank one on the way to the lake. Ok, I'm a light weight. I had a mild buzz, and drank the next one MUCH slower. Charles just watched, and finished off his second one. We walked to the lake, and took off our shirts and shorts, and headed into the water. Man, this beer drinking is all right. I don't think I ever felt so mellow. Charles immediately dove in, and swam way out in the lake. I was a lot more cautious and waded out until it was deep enough to swim. This was cooler than I imagined and I regretted even second guessing coming. The sun and the water felt great. I leaned back and just floated, feeling a calm I could not remember. I lost all track of time, and wondered had I fallen asleep. No way, I would have sank below the water and choked.

I didn't even hear Charles swim up to me, until he said, " Hey, champ, we should probably go in, you'll get a sunburn, if you stay out too long. " He smiled big and continued, "It's easy to lose yourself out here, isn't it?" I grinned and thanked him for bringing me. I helped gather wood, and he taught me how to set a fire. He then brought out hotdogs, buns, and chips, and, of course, more beer. The sun set and the fire was cozy.

I was not used to this simple beauty. There had never been a male figure in my life, that just treated me like a person, and I was high on this new feeling. (Well, yeah, the beer too, but, you know what I mean. Charles showed me Constellations, tried to teach me corny campfire songs (which led to much laughter). I figured this must be what having a Dad was like. My Mom was great, but this was a whole other part of the human equation. He asked me about my life... school, girls, my ambitions, dreams, and I felt a genuine interest there. Not like I originally thought, that he was just doing a favor for Mom, but that he wanted to help me.

While we were fishing (he fished, and tried to give me pointers) He asked again about girls. He must have seen me blush, and told me no matter what we talked about, it would stay between us, that he wasn't trying to get information for my Mom. He continued, saying that a young man my age had to be interested, and I nodded, but didn't say much. He asked if someone had broken my heart and I stammered out, "N-no, it...never got that far." He patiently waited for me to explain, so, finally, I shrugged and said, (very red faced) "I...don't have anything... to umm... offer girls." He looked puzzled, I sighed, cleared my throat and said,

"I went out with a girl I liked, and I think she kind of liked me. On our third date, we were making out and it was going great. I got to feel her boobs, and got my hand up under her skirt, when... (deep breath) she put her hand on my...crotch. She got a funny look on her face, kind of puzzled, and unbuttoned my jeans, and unzipped me. I.. really don't want to talk about this."

"It's ok, Truman. No matter what, it stays between us. I'm just here to help you, ok? So? What happened then? Did she give you a hand job? A BLOW job?"

My face went redder, as I shook my head. "No. I...think she was GOING to, but...but...(I blurted out) She LAUGHED at me! She said, that's no cock! It's not much bigger than my clit!" I dropped my head, my face in my hands.

"Oh, man, that must have stung. Why was she so mean?What a terrible thing to say." He looked so sympathetic.

"It WAS mean... but... she was right. I'm not like most guys, I guess. She said I'd never be able to please a girl, because... it's too small."

Charles just sat there for a few minutes, trying to look like he was concentrating on his fishing line, but I figured he was trying to think of what to say next. We sat there another hour, he was deep in thought. We gave up fishing, put the gear away, and went swimming for a while. That took my mind off of that horrible conversation temporarily, then we had a late lunch, broke down the tent, and loaded up the gear.

On the way home, he acted like nothing had changed and asked, "So, Champ, what do you think of camping? Want to try it again next week?"

I have to admit, I figured this was a one-off, but he was asking, so, of course I said yes. I had bared my soul, but he didn't hold it against me. When I got home, Mom of course asked what I thought about camping, and did I have fun. I said yes, but it was mostly just relaxing, unwinding, and that I thought Charles was a nice guy for taking me. She agreed. The week following went by normally, but by Friday, I was getting excited to get outdoors again.

Saturday morning, bright and early, Charles came over, and we headed out. We were barely 5 miles away, when Charles looked over at me. "Truman, do you trust me?" He waited until I nodded yes, and continued. "I've been thinking all week about your situation. No one should have to go through life unfulfilled. I'd like to try something radical, IF you trust me completely. Ok? If it doesn't suit you, we won't ever have to mention it again, and no one has to know, except us. We're taking a detour." With that, he smiled and we headed to the nearest town that was still in the direction of the lake. My mind was whirling, trying to figure out what Charles had in mind, but he wasn't saying. On the way, though, he had me drink a couple of beers, and gave me a tablet of something he said would mellow me out. Thinking that I might need it, I swallowed it down.

We pulled up to a beauty shop, and I quickly said, "I don't think I need a hair cut," and he laughed (My hair was just over my shoulders.)

"You're probably right, Champ, but let's let the expert decide." We went in, and a middle aged lady was waiting on us. "Clair, this is the friend I told you about. What do you think? Can you do your magic?" She smiled, winked, and answered that as long as I was willing, she could. I was feeling the effect of the beers and the little pill, so I sat right down in the stylist's chair. She started washing my hair (wow, it feels amazing when someone ELSE does it), and without being aware, I dozed off. In the back of my mind, I could hear whispered voices, but felt too good to make myself wake. I could feel her soft fingers on my face, neck, and I dreamed she, or someone, was removing my clothes. Part of me remembers rolling side to side, helping as my shirt, shoes, socks, shorts, were removed. I can't recall why, but, for some reason, it did not seem weird. Was she massaging my legs? I could feel soothing tingling, and I may have been moaning.

I don't think I've ever slept this well before. I was the poster boy for calm. I think I was being pulled this way and that, as my clothes were going on, but it was so gentle, and, in my mind, maybe a bit erotic, that I liked it. I wondered why my clothes were removed, just to put back on, but it was fleeting. Had they been washed? The material felt so soft. Something was brushing my cheeks, then my lips, and then eyelids. Not quite like a tickle, but almost. The voices were seeming louder now, more excited, and I felt a light stinging above my eyes. My eyelids began quivering open, just as the stinging stopped, and Claire's voice, very clearly said, "There, all finished! Doesn't she look sweet?" I slowly focused, looking around for a "she."

Charles and Claire both were staring right at me, smiling so big, but I scanned the room to find no one else here. I felt... different. The effects of the little pill? I leaned forward, about to stand, when I froze. Those are NOT my legs, shooting out from a short skirt, and NOT my feet, in sexy little heels. I looked around. "Wh-WHAT is going on? Am I still sleeping?"My hands are sliding down my body, but not my body, in a lacy blouse, and...a bra? I know I looked lost, because both Claire and Charles got on either side of me, and slowly pulled me out of the chair, turning me until I saw my reflection the the mirror.

At first, I was stunned, then mad, then confused. WHY had they done this to me? I kept looking at that mirror, still not convinced it was me.

"What... have you done to me?" There was a pretty girl, open mouthed, staring back at me. Except for KNOWING it's me, I couldn't have imagined it.

Charles said, "Tru...(accidentally, or purposely, leaving off the man, I'm not sure), Tru, I, uh, we, figured, given your, um... shortcomings, this ... might be another choice for you. If you...hate it, it's easily undone, but, could you give it a try? You make a damn cute girl. What do you say? Give it a chance?"

Clair popped in, "He's right, Sweetie. No one will guess you aren't all girl, unless you tell them. Give it a try. Walk around in the heels a bit, to get the hang of it. The silicone inserts in that lacy bra fit you perfectly. If I were half my age, and bi? I'd be all over you."

I swallowed hard. "Are you...sure? What made you think of this? I'm not...gay, or anything." (directed at Charles)

"I know, Champ, but, you seem so lonely, and everyone deserves to be happy. And, you wouldn't be gay... you'd be a girl."

I turned back to the mirror, twisting side to side. I wasn't sure about all that, but, I DID look like a girl. What would Mom say, if I came home like this? "Well, um, what do I do, now, dressed like this? How will I know if this feels right? Cause, it sure feels strange right now."

"I thought that out too, Tru. I think we should maybe go to the mall, let you see how people respond to you, then a restaurant, then, I know a bar I can get you in. Do you know how to dance? I'm positive you'd get some attention."

"Woah, woah, slow it down. I...need to um, take baby steps. And, we need to not forget my clothes, if I freak out too much in...THIS"

Charles paid Claire (I don't even want to guess what all of this cost) and we walked slowly to his truck. I instantly was aware of how the heels made my hips sway, and I won't lie, I liked the way the short skirt hugged my hips, legs. I would definitely sleep with me... if I only COULD. Getting in the truck, I had to tug the skirt down, as it rode up a lot trying to climb in the seat. A LOT of leg showed, causing me to blush, but also excited me. Holy Shit, I DID look like a girl. Riding along, I got a few sidelong glances, and Charles would ask if I was ok. I simply nodded. I subconsciously licked my lips. The pink lipstick felt so strange, but so...SEXY. WOW! Ok! That's erotic. Maybe... this ISN'T as crazy as it feels.

While we are riding, I'm fumbling with the purse Claire provided. I was surprised to find more lipstick, eyeliner, mascara, makeup remover, and FUCK! CONDOMS?? What does she think I'll be doing? Charles noticed my blush, but didn't ask. When we pulled into the mall parking lot, Charles came around to my door, offered his hand to help me out. "Just, breathe,Tru, you can do this, you really look great."

He patiently slowed his wide gait, to match my smaller stride. Mindful not to stretch my legs too far, and try to control the sway of my hips. "If anyone asks, which I doubt, but, if they do, you're my daughter, ok? Charles' big smile was so comforting. I wanted to just hug him. He really was doing so much, trying to help me.

We strolled the mall, he asked if there were any stores I wanted to go in, and, if I wanted any other "girl things". "I can't think of anything I need, can you?"

He thought for a moment and said,

"Well... what about a swim suit, if we go back to the lake?"

My mouth popped open. I hadn't thought that far. Would I still look like this, at the lake?

"How about this. We'll get you one, and, if you decide you don't need it, we can always return it. Deal?" I nodded, and in we went. Even though my face stayed red the whole time, we picked out a red bikini. And, yes, I DID wonder what I'd look like, in it. For the first half hour, I was very nervous, I just KNEW someone would spot me, and call me out. Little by little though, my confidence grew, as I watched men, mostly older, but a few young guys, giving me the eye. A few weren't even subtle, but whistled and called out things like, " I'll show you what a real man feels like," to the crude ones, "come get a mouth full of special sauce." That one caused Charles to chase the guy away, but we both laughed later.

"See", he said, "no one can tell. You are just a hot girl to them. This might work, if you let it." Ok, yes. I liked the attention, I'd never had any. I loved the thought that people, well, guys, were attracted to me. But, could I... want... SEX? With guys? That was the kicker. I'd always dreamed of getting my pleasure FROM girls, not from acting like a girl. And, what the Hell would I do? For the first time, EVER, in my life, I imagined looking at cocks. Not tiny ones like mine, but real ones. Could I touch one, caress one, or... MORE? I caught myself glancing at crotches, and then the face that matched them. I realized, quickly, it was easier to imagine that possibility, with me looking like this. After all, that's how girls make guys feel good.

I think Charles felt that I was getting more comfortable, looking like this, because we left the mall and headed to a restaurant/bar. As we walked in, he leaned down and whispered, "Just remember what you look like, ok? Everyone here sees a sexy young girl. Go with it." We sat at a table in the middle of the room. At first, I tried pulling at my skirt, because a lot of my legs were showing. I gave up, though, it was pointless. The place had "ambiance", I guess... Not a lot of light, and candles on the tables to see your menu with. Charles ordered me a wine, and to my surprise, the waiter didn't flinch, just brought it to me, and a beer for Charles.

It sounds silly, maybe, but I "felt" so feminine, sipping my wine with dinner. I found myself acting more "ladylike." It was not lost on Charles, as his smile got bigger. I was his creation, I guess, After my second glass of wine, I quickly realized, what goes in, must come out. I whispered that I needed to use the bathroom, and Charles quickly told me to go in the ladies room. I wasn't sure about it, but he nodded. When I stood up, I had to hold the table for a moment. He chuckled, and told me to walk slowly, I'd adjust to it. After a few steps, I did right myself, and don't think I wobbled much.

The two bathrooms were side to side, but I found the ladies room door locked. I knocked, and heard a voice answer, but couldn't make out what they were saying. I got more nervous as I did a little dance in the narrow hallway, trying to wait. After what seemed like an eternity, I shrugged and stepped into the men's. I could NOT hold it any longer. I quickly slipped into a stall, and pulling down my panties, sat.