tagTranssexuals & CrossdressersI've Finally Found Myself

I've Finally Found Myself

byClintdear©

When I was eighteen, I loved to dress up in my mother's clothes. My little boner would rise with anticipation as I would search for treasure in her hamper. Once, when I was home alone from school I added makeup to my play. I had panties and a bra, a girdle, and a copy of Cosmopolitan to guide me. I sat at my mother's make up table and began to learn about myself. I experimented by copying as best I could the make up on the models in the magazine. When I was done I realized that for the first time in my life, I had made a decision as to who I wanted to be.

One day, as I wandered around the house in my feminine persona dressed in mother's baby doll and satin robe, I noticed as I walked by my brother's room I would get turned on. My face would flush and my nipples would rise and become tender as my little penis would stiffen. There was definitely something dark, foreboding, and sexual about that room that made me feel aroused. As my curiosity led me inside, I was greeted with mysterious odors of masculinity so unlike my own – mixtures of sweat, testosterone, and sperm. I felt an unmistakable vulnerability to masculine power, and yet it drew me closer, calming me with sexual purpose. I truly felt like a little girl in a big man's world. As I stood there soaking in the vibrations of power and sexuality left behind by this mature male, I picked up my brother's sweaty tee shirt and brought it to my face. My heart beat faster as I closed my eyes and deeply inhaled his scent. I felt warm and calm as a rush of sexual arousal spread throughout my body making me starkly aware how much I craved the sexual attention of a man. Intrigued, I found some more treasures to experience until finally I found his underwear and brought the musk of his ball sack to my face and inhaled. I immediately surrendered to this new awakening and began to rub my stiff little penis as I explored the wonderful sensations in my nipples. My senses were alive as my inner girl began to reveal her true power over me, as I closed my eyes and imagined being chosen by a powerful man to be his mate as I reached a powerful climax.

As I got older and moved out on my own, I gravitated from crowd to crowd. Being a young and single 20 something presented me with lots of room to explore. I went to one pretty tame party where same sex attachments weren't totally off limits, so I found myself able to relax and to begin checking out the boys. There were a couple of obviously gay guys who I thought might try to hit on me so I made a point to be chatty and friendly with them, hoping they would sense I was available. I was flattered at the attention and tried to return it, but they just didn't pursue me even though I warmed to their hello and goodbye hugs, and looked forward to the occasional sneaky kiss on my neck, as if they were teasing my growing hardness. I'd hold their embrace hoping to generate some interest but they'd always just let go. I wanted their companionship, to be one of them except they didn't seem to be interested in me even though I made my yearning for them painfully obvious. I felt defeated and decided it was time to get creative if I was ever going to have a boyfriend.

When I prepared for the next party I decided I would experiment and try some mascara to make my eyelashes longer and prettier. I liked the way it turned out so I added a little light gray highlighting above my eyes, and a bit of rouge on my cheeks. It would be pretty much invisible unless you were very close to me. I was alone and unattached. I wanted to feel sexy and I didn't see anything wrong with wrong with that. I wasn't very masculine anyway at 5'7" 120 pounds. My face was naturally very pale and feminine and I wanted to accentuate my pretty face with a little accent here and there. I was blessed with delicate features and more hips and chest than many girls my age, and the rosy cheeks and the long eyelashes I created helped me decide that maybe I should just be myself and forget the roles and labels.

Intrigued with my appearance, I decided to spend some time grooming my feet. I started by shaping my toenails and removing any hair and calluses, and worked the cuticles to increase their attractiveness. I smoothed and polished my toenails until they glistened. Next, I added a subtle pink polish and whitened the ends of my toenails to give myself the best French manicure I could.

So as to show off my toes in a quietly sexy way, I put on my low-rider bell-bottoms without underwear for a smooth appearance, and the extra length allowed my cute little piggies to peek out from under my cuffs. I finished them off with a toe ring for each foot. I could not resist the temptation to slip into a pair of girl's sandals I got in the young women's department at Walmart. My pretty feet deserved that.

I put on a thin white top that was snug enough to show my boy-boobs if I let my thin jacket fall open for the right guy. Looking in the mirror I could see my areolas and nipples quite easily with a hint of a bust line. I combed my longish hair back into a ponytail and captured it with a pink scrunchie.

I walked the short distance to the party, getting used to the new me. The "me" that had decided it was time to find a boyfriend and see if that was what I was lacking in life. All they way I was wondering, exactly what do boys and boys do together? I'd love to hold hands and kiss a handsome boy.

I arrived at the party, and chipped in my ten bucks and bought myself a wine cooler and decided to try to stay calm and get used to the action and most of all get used to being "me".

As the music played my instincts took over as I moved my hips to the music in a distinctively feminine sway as I absently checked out the guys. I noticed many of the couples were of the same sex, which helped put me at ease. It wasn't long before several guys were hovering around me trying to catch my gaze. I accepted quite a few dances from quite a few handsome boys, all showing their appreciation by not stepping on my toes while they rewarded me with jabs of hardness to show their interest. I was shocked and embarrassed at the shamelessness of some of these boys, yet they made me feel so small and powerless. I had never felt so desirable in my life! Yet, I felt powerful knowing I had affected boys this way. They wanted me and it showed. As they advertised their desire, they suckled my earlobes and breathed with hot shallow gasps. I could feel my resistance fading as I absorbed the pheromones of the males I had aroused and I found myself pressing back against their hardness, inviting their stimulation, knowing this was the night I had been waiting for. I decided it was time to find a mate out of all these restless suitors competing with one another to make me surrender and become theirs to love.

I made eye contact with a particularly cute guy. He was a big, tall, twenty something guy and he smiled back at me and winked as I beamed and returned his smile. It was still a little scary to be looked at sexually by another guy, but I was getting my courage up, and I really hoped he would come talk to me. I was imagining just how happy I would be if I could land a hunk like him for a boyfriend.

As I was daydreaming watching all of the couples dancing and having fun, the cute boy who winked at me came up and sort of loitered near me. He was at least 6'4", well built, and seriously manly at the age of 20 something! He was making me a little apprehensive as I realized he was drifting toward me. I felt my heart beating more rapidly as I sensed him closing in. Thinking to myself, I wondered if this was such a good idea, until I realized it was too late and I have done what I hoped to do: I had attracted the sexual interest of a man. Since I'd had seen him around before and he always met me with a friendly simile, I felt fairly safe and I quickly decided to follow my instincts as he slyly moved into my space.

"Hi there. What do you think of the party?" He asked.

"So far, it's been fun watching the people. How is it going for you?" I replied.

"Boring. I haven't seen anyone I know or am interested in knowing."

"What's that supposed to mean?" I quizzed.

"I didn't mean you. I'm sorry. I've seen you around and wanted to get to know you and see if you'd like to hang out. I'm Kenny, buy the way."

"Ok, I'm fine with that. Pleased to meet you, I'm Carl." I replied as we shook hands. I kept my handshake weak and soft and he held my hand longer than a simple handshake. We were practically holding hands when he startled me by putting his arm around my shoulders and moved me away from the action.

"I feel like a little kid next to you! You didn't think I was a girl did you? It's happened before, I'm ashamed to say." I teased as I looked up into his eyes.

"No, if I thought you were a girl I wouldn't have hugged you." Kenny said.

I smiled sweetly and replied, "Tell me more!" I cooed.

"Can I hug you again?" He asked? Before I could answer, he pulls me to him and holds me against him. I though he was going to try to kiss me, and I lifted my face to accept! But instead, he zips me up in his jacket with my face just below his chin! I was freaking out inside as my heart raced as I realized I was zipped up inside a man's jacket with him in it! I didn't know what to do with my arms, so playing my role as his captive, I relaxed and decided to play along and wrapped my arms around his muscular torso. Then I began to get hard. Real hard, thinking uh oh, he's going to feel it and kill me!

"Now isn't that nice and cozy?" He asked?

I didn't know what to say but it was definitely warm and cozy, as well as musky and manly, and I could feel my gentle giant getting a hard on against my stomach. Here I am trapped and squeezed to his body and he is happy I'm a guy. Is this how it happens?


Kenny put his arms around me and maneuvered me into a corner. Then he squeezed me to him and asked, "Do we have something in common, sweetheart?" As scary images flooded into my mind about men and their sexual arousal, I realized something was different here. I actually liked being touched by Kenny this way, and it was turning me on as he pressed his hardness against me. It was scary to feel him poking into me with no shame, but I wouldn't have run away if I had the choice. My stomach was full of butterflies and my heart was racing, but I knew this was special. He made no effort to hide his arousal as he pressed it against my stomach, and arrogantly leaned into my lips with just a peck at first to see if I was receptive. I closed my eyes and tilted my head to let his tongue glide into my mouth as I shivered with anticipation as I received my first kiss as Kenny slid his warm hands inside the back of my pants to caress my butt cheeks. I was steaming with lust!

"Would you like to go somewhere quieter and meet someone with me?" He asked as he slowly unzipped his jacket to free me.

"Yes, I think I'd like that." I replied with a grin. I was smiling inwardly at the world's oldest pickup line until it dawned on me that I just agreed to be "picked up" as Kenny made a cell phone call. I was wondering what was going on, but whatever it was he was smiling as he was talking, so I didn't think I was being measured for cement boots.

So we eased ourselves out of the party to Kenny's motorcycle, and he told me to "hop on". I didn't know what to do since I'd never been on one before.

"Put your arms around my waist so you don't fall off and lean against my back so I know you are still there. You need to lean with me as if we are one person. There. Squeeze tighter, and put your hands under my jacket to keep the wind from going up your sleeves making you cold."

I did as he asked thinking, is this really necessary? Is this some "guy" trick? But then I realized maybe this is how boys flirt with boys who they have just kissed. I struggled with the ins and outs of why Kenny is interested in me and why I actually let him kiss me. I was having second thoughts as to why I left alone with him as we roared off on his motorcycle. I was trembling with fear and holding on for dear life with my cheek planted tightly on his back as I ruminated on just what having sex with a man would entail and how I would act when faced with the reality of actually doing it.

He must have thought I was crying but I was laughing about a tee shirt I saw once that said: "If You Can Read This, The Bitch Fell Off!"

We're almost there! Hang in there." Kenny said as I giggled to myself for cracking a funny. He reached under his jacket and gently covered my hand with his to reassure me of my safety. Bravely, I opened my legs wider and pressed myself closer to him as I held on tighter and smiled warmly to myself as I realized my hands were resting on his denim-covered penis. I wondered if he could feel my hardness pressing against him, but I was beyond caring. I decided He was boyfriend material and I had to see where this led.

We pulled up to a nightclub and disentangled ourselves from the motorcycle and Kenny led me into the club, opening the door for me like a boy on a date and guided me in with his hand on my lower back letting his fingers gently glide down to gently cup my butt cheek before he removed his hand. Finally we found a table and sat down and a tall, strong looking girl came up and sat down next to Kenny like she was a girlfriend or something. Oh oh, I'm thinking.

"Hi baby!" She gave Kenny a little hug and I began to feel the blood rush to my cheeks.

"Hi Mary! meet Carl. We met at a party across town. Excuse me while I get us some drinks."

Thanks for abandoning me Kenny dear. Shit. What am I suppose to say?

"Hi there. I'm Kenny's sister. How are you and Kenny getting along?" she asked, smiling.

I blushed red as a radish. "Fine. He seems like a real nice guy."

Staring right into my eyes, she says, "Yes he is. And you are the first boy I have ever seen him with. He doesn't seem to like girls, but I do think he likes girlie boys!"

Oh great. My heart is in my throat with cold fear. "I can't help it if I'm smaller than most guys. I mean I'm really not that way." I squeaked.

"Really? Kenny called me before you two came. I know he likes you and I know why." She said smugly.

I gulped, "Why?" I asked stupidly.

"Because he is gay, but doesn't like men. It took a long time for us to figure it out let alone for him to find a nice person to even hope to begin a friendship with. He called me because he trusts me, and he's excited to have me meet you."

My eyes were as big as saucers.

"Tell me about yourself, my dear." She reassuringly put her hand on mine and looked deeply into my eyes.

I began with the usual stuff and Mary held up her other hand and said, "Stop!"

I stopped mid sentence, mouth agape.

"Carl, are you gay?"

There it was in plain view.

"I don't know."

"I think I see makeup, am I correct? Answer me."

"Yes, Ma'am." I replied.

"How long have you wanted to be a girl, so to speak?" Mary asked.

"Ever since I can remember, but recently I've decided I want to meet someone and find out what it's like to have a boyfriend. I don't feel any sense of equality around men. They are strangely different from me yet this difference seems to create a sexual attraction in me. So I decided to listen to my inner feelings and see what would happen, and that's why I tried some make up. I decided to see if I have what it takes to attract a guy. So, when life gives you lemons you make lemonade!

I felt like I was being tortured like a mouse by a cat, and yet somehow I trusted my torturer to lead me in the right direction. I bared my soul to Mary. I felt we were in sync and she understood. Mary put her arm around me, and pulled me to her and whispered, "That's ok, sweetie, I think you're a wonderful person and will make my brother a great sweetheart. He wants you to be his girl in his relationship. I think if you can just be yourself, you two will get along fine, and I'll be happy for you!"

I guess she saw the relief in my eyes that the inquisition was over. She leaned back into me and asked me, "Honey, would you like me to touch up your make-up? Just a little pinch would be cute. I'll bet Kenny would love it! You have wonderful features. I'll bet your mother was beautiful!"

Not daring to say no to this woman, and at the same time realizing I may have reached a place I've always wanted to go with someone I trusted, I agreed.

Mary took me into a unisex bathroom and locked the door. She brushed my longish hair out and styled it a little. She put some rouge on my lips and covered it with shimmery pink lip-gloss. It looked and felt great, but wasn't thick like lipstick. She used some more rouge on my cheeks to brighten them up a little, and put the slightest light gray on my eyelids. Next she took a tissue and gently brushed the powders until they were nearly invisible, mere hints and highlights. She opened the top two buttons of my shirt, and pulled out the tails I had tucked in and tied them in a knot, to show off my midriff. Then she pulled my low riders down even lower, almost to where my downy pubes were showing. I learned to trust Mary. She had no plans to make a fool of me. She stood behind me as I looked in the mirror, and caught the radiant smile on my face as I saw her handiwork. She smiled with me and said, "How long have you been a girl?" as she dabbed a tiny bit of perfume on my neck and gently kissed me on the top of my head.

I smiled a wide smile and replied, "When I met Kenny!"

Finally Kenny disengaged himself from his buddies and came back over.

"Hi Princess, how are you and sis getting along?" as he slid into the booth and put his arm around me. He brought me a rum and Coke, and Mary a Coke.

"Just fine." I replied as we both smiled.

"I can tell. You look ravishing Carl. Can I call you Carla?" he asked.

Oh boy. Why do I have to make all of these decisions right now, I wondered?

"No, I think I'd like you to call me Cherie." I replied. I had no more fight left in me.

"Cool. Will you dance with me?" Kenny replied as he pulled me up by my hand.

We danced a nice slow dance like lovers should. He held himself against me as I put my arms around his neck and again I could feel him hardening against me again. I was pleasantly surprised to have such power over such a big guy, as I rested my head against his chest, his hands caressed the sensitive flesh of my back. As the song ended he turned me so his back was to Mary, and ran his hands gently down inside my pants and caressed my ass cheeks and kissed me gently as I stood on my tip toes to get as much of him as I could.

"Will you come home with me? I promise I won't attack you. You can sleep on the couch if you'd like. It would be wonderful to have breakfast together." Kenny asked.

We returned to our booth and Kenny told Mary we were going to get going. Mary sweetly smiled at me and responded, "I think she should come home with me. You kids have had enough fun for one evening. Besides, we are still getting to know each other. Come over in the afternoon after work, ok Kenny?"

"Ok, Mary. I'll see you tomorrow. Bye Cherie. I'll see you tomorrow, too." Kenny replied a little dejectedly as he leaned in for a peck on the lips, and Mary sat by and studied me as Kenny headed out the door, and we headed for her car.

"Cherie, would you mind if we made you up into a really pretty girl tomorrow? I think it would be fun, and we can hang by the pool and talk about girl things. What do you say?"

"Yes ma'am." I spoke as if I was a child or something. Mary was definitely the alpha wolf here.

We arrived at Mary's house, and she points me into a bedroom and says "Good night, sweetie. I'll see you in the morning"

Morning arrived and I lay in bed and began to wonder if I was doing the right thing. It seemed that Mary was definitely in charge. I wondered why Kenny didn't argue with her, but then I realized that maybe she was trying to protect me. I still hadn't come to terms with the idea of having sex. I wanted to on an emotional level – it was all I could think about, but I was drawing a blank on the physical part. In short, I didn't know what to do or what to expect. I decided to get up and face my new world and see where it took me.

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byClintdear© 9 comments/ 119832 views/ 38 favorites

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