My First Trip Out of the Closet

By missunderstood98

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Tags: walking on the wild side

Added: 13 Jan 2009 Views: 14611 Avg Score: 4.62

Crossdressing fun way over the edge

  I have wanted to write this story for many years but I hesitated to do so out of my fear of the unknown.   Since moving to Florida , I have pretty much been on my own for the first time in a long time. Let’s just say that now that I am older, I’m bolder! I no longer care who knows my sexual interests. It’s funny, because everyone I currently see understands my desires and approves of my different fetishes.


Foremost of these, is my predilection to live my non-professional life as a woman. I love dressing, going out, especially shopping and going to the beach, socializing and SEX, with both men and other women.


The first time I found what is was to be transformed into a pretty young girl was the summer following my 9 th grade school year. One of my girlfriends, Mary, had constantly teased me about what a pretty girl I would make. She constantly pestered and hounded me to let her try and make me up. She would often tell me that if I let her do it, then it would be our little secret.  


Well, I could take it no longer. She finally wore me down and I gave in. Little did she know,   I secretly was curious to let her have her way?   At thirteen, I even became aroused dreaming of what might happen if I was allowed to live periodically as a female. What doors would open up for me? I mean, we all know how little girls always get their way. Right?     


In late June, with all of our friends leaving town on vacation, Mary invited me to spend a weekend with her. Our mothers saw nothing wrong with it. They actually thought it was sweet of her to ask and I should not refuse her act of friendship.


Mary’s mom worked during the day. Her father would be away another week on business, and her older sister, Sarah, had one more week of band camp. The days were ours and we didn’t waste a moment!


On Friday morning, Mary woke me with a kiss. Her first words were, “Let’s go, you’ve got plenty to do.” Mary led me to the bath and we shared the tub. We were both the same height, 5’ 4”, and weighed about the same, 110#. The difference was Mary was a very mature thirteen years old. She sported 34D size breasts. They were big and firm. Her nipples stuck out like “chapel hat pins”! As she dropped her sheer, baby doll pajamas, I could only stare in amazement. “We all knew you were stacked,” I commented, “but, wow, if the guys could see you now!” She smiled a wicked smile and invited me to take off me my PJs and join her in the tub. I was a little shy, since I was aroused and my dick was growing. She smiled again as I stepped in the tub. She immediately touched my cock and laughed at its uncontrolled growth. It was no longer than 4 or 5 inches but it was solid.

I moaned out loud as she stroked me under the water. I opened my eyes and moved closer to her. Our lips met and our tongues pierced our lips. We both tried to get our tongues deeper into one another’s mouth. I guess I won but who cared! It was Mary’s turn to moan as my finger found her clit. I rubbed it hard and then slipped a finger in her honey pot. She stated bucking her hips as I increased the tempo of my probing. She let out a gasp and shuttered, as her orgasm overwhelmed her. It was incredible how much she enjoyed it. I soon found out why.


I moved away from her and started soaping myself. Mary came down from the mountain and grabbed my neck and kissed me hard. She leaned back and began telling me of the wonderful feeling I had just given her. My cock, still hard surfaced in front of us. Mary wasted no time, grabbed it and started pumping. She then did something I never expected. She lowered her head and kissed my dick. She actually made love to it like it was a third person in the tub. In no time, I stood up, grabbed the sides of her head and began to face fuck my sexy temptress. I couldn’t last and screamed, “I’m Coming!”

Mary didn’t blink and as I came, she sucked all of my teen love juice out of my cock and swallowed it all.


We both just fell back and laid there in joyful bliss. Mary regained her composure and said, “I’ll wash you, if you do me?” I joked, “I already did you!” With that, we both laughed and completed our bath.


After drying each other, we hurried to Mary’s room. She told me she wanted to style my hair. Now this was the early Seventies, most of the guys had long hair. Mine was real long, well past my shoulders and white blond. Mary got out her curlers and put several into my hair. As she played, I felt another erection beginning to stir. As it grew, my “little secret” was no longer a secret. “You’re really into this, aren’t you?” Mary said knowingly. I could not deny it and began to tell her several of the erotic fantasies I had been thinking of prior to this weekend. Mary smiled, patted me on my knee and cooed, “You have no idea?” With that said Mary leaned down and started to suck my dick. I was rock hard in moments. This time she went slower and teased me. She kissed my head and licked down my length until she got to my nuts. She licked one at a time, all the while jerking me off. When I told her that I could feel it starting to erupt, she went back to the tip and waited for her reward. I came and deposited another load into her mouth. Unlike before, Mary did not swallow. She held my cum in her mouth and rose to kiss me. Before I could react, Mary pushed her tongue into my mouth and I got my first taste of male spunk. “How was it?” Mary asked. I smiled and nodded my approval.


While we waited for the curlers to do their job, she painted my fingernails and toes with “Hot” pink nail polish. Afterwards, Mary began applying makeup to my face. She explained that during the day I would wear a light coverage of makeup. Later tonight we would go out and she would really make me up.   Mary started with a light coat of pink foundation. She put mascara on my eyelashes and used this device to curl them. She concluded by painting my lips with “Hot” pink lip gloss. All the while, she kept me from looking in the mirror.


I started to worry about what I was going to wear. Even though Mary and I where similar in size, it was obvious that I couldn’t wear her stuff. I ask Mary what she had in mind for me to put on. She laughed and told me not to concern myself. She said I could wear some of Sarah’s things. Sarah was sixteen. She was also our size but built more like me then like Mary. We got up and went to Sarah’s room. Mary showed me her undies and told me to choose whatever I liked. My choice was a matching pink bra and bikini panties set. I slip into the panties and they fit like a glove. Mary helped me with the bra; she adjusted the straps and put it in its place. She looked at me and started to laugh but my look signaled her to stop. She said not to worry and pulled two “falsies” from another draw. She then inserted them into the bra and adjusted them properly. Next she pulled a pair of cut-offs out and handed them to me. Mary stood there a moment, with one hand on her hip and with the other scratched her head. A light went on in her head and she exclaimed, “I’ve got it!” She went to another drawer and pulled out a short-sleeved pink crop top. On the front was printed, “I like boys and girls.” After I put it on, we looked at each other and both of us started to giggle. Mary went to Sarah’s closet and pulled out a pair of 3” wedged sandals to complete the outfit. Mary took my hand, put on three or four bangle bracelets, a pink watch and several different silver rings. We returned to Mary’s room where she proceeded to put herself together. Mary started with a sheer white bra and panties. You good see her nipples clearly through the material. Since Mary has dark brown hair you could also see her entire pussy. Standing there, Mary appeared to have no undies on at all. I immediately felt my third leg trying to get out of its confinement but Mary had situated everything in its proper place. I stood there with my mouth agape, feeling like I shouldn’t be staring so wantonly. Mary broke the silence and told me to sit down so she could comb out my hair. When she was done she stood back to admire her handy-work. “Oh my God,” Mary exclaimed! “Look!” I did and found myself looking at this cute, sexy, teenage girl staring back at me. I couldn’t believe my eyes. I had been totally transformed. No longer could I ever deny the obvious. This creature I was looking at was really me. If I hadn’t witness the event, I would be hitting on her trying to get into those skimpy cut-offs. It was Mary’s turn to ogle. She spoke up and said that she was glad that I was me because she would be tempted to go lesbian all over me. I laughed and told her she would have her chance later. I said, “What are we going to do now.” Mary put her finger to her lips and then touched mine. “Let me finish dressing and we will go to the Mall.” “The Mall,” I caught myself saying. “I can’t go to the Mall,” I retorted, “What if someone sees me?” “So,” Mary exclaimed, “You didn’t even recognize yourself.”              


I went downstairs to get a drink while Mary finished. When she came down, I just whistled. Mary looked so hot! She had on a “barely-there” mini skirt, lace tank and 5” platform sandals. I thought to myself that we would be two of the hottest babes at the Mall. We left without eating and caught the bus downtown. I had trouble walking at first but when we got on the bus everyone, including the ladies check us out. Mary looked at me and we giggled again. My confidence was souring. We exited the bus at the Mall and went inside, strutting our stuff.


We walked around window shopping. We caught the eye of every male insight. I was delirious with this new found power. It was as I had imagined it would be. I was a girl! I was a sexy, pretty girl that every man wanted. I felt free. Free to explore a side of me that I dared not allow out before. Now, I could care less. As we strolled around, I began to let my hips sway. I would stop and flip my long hair as I acknowledge a guy staring at my beauty, my sexiness, my wanton attitude.

I told Mary that I was hungry. We went to the food court and made another scene. No matter where we went, there were males of every age, shape, race looking at us and wishing we would stop and sit on their face!


I stood in line, waiting to order, when I turned and saw Mary chatting up four good looking guys. One had placed his hand on her butt and was squeezing it. I was getting jealous. Then I thought to myself, I can’t because he is not my competition but my prey!

She looked at me pointing and the guy took his hand off her ass and waved. “Oh my god,” I thought. “What have I gotten myself into this time?”   I got our burgers and drinks and slinked over to the group.


“Johnny, this is my new friend, JOY,” Mary introduced us. Johnny introduced me to his three buds, Luke, Dan and Allen. Mary grabbed my arm and led us to the nearest table. The guys waited and watched us walk away. They look at each other and were probably trying to decide how to divide and concur.


“JOY,” I said to Mary. “Why did you choose that one?” Mary just said, “It was the closest girl’s name to yours that I could think of at that moment.” “Anyway, you look like a Joy to Behold today.” That caused us both to giggle. “So tell me, I asked, who are these hunks?” Mary said that Johnny was a senior at the high school we were to attend in the fall. He was her counselor at the summer camp she went to several years ago. He saw her and couldn’t believe she was the same girl. She had filled out so nicely. “They asked if we would like to go with them to Johnny’s family lake house this afternoon. “I told him it was up to you,” Mary said as she just grinned and licked her lips. “That’s nice, I answered, “There is a slight problem!” “I’m not what I appear to be,” I cautioned her.

“Don’t worry, JOY,” Mary went on, “Just follow my lead.” I just shook my head as I took another bite and sip of my drink.


The boys came over to us as we finished our food. “Well, what’s it to be?” Mary spoke and said we would go but first we had to stop in the swim shop and get us a bathing suit. “Why?” Allan spoke up, “We thought you two would go skinning dipping with us.” Mary just waved her finger at him. “Not today but maybe another time.”


Mary and I went in the Bikini Store. The guys hung around looking to catch a glimpse of two sexy bitches without their clothes on. Mary and I checked out the petite rack. Mary chose a bikini that would barely cover her nipples and pussy. I had to be more discreet. I chose one with a French bottom and halter top with built-in, under wire bra. I was gitty. I was about to buy my first, very own piece of female attire. Mary called me to join her in the same changing booth. They were located around the store right out in the store. She told me to try mine on first. I took off my shoes, shorts and top. As I was slipping into my suit, Mary opened the curtain and gave the guys a little show of my ass wiggling into the bikini bottom. I turned around after putting on the halter top and saw Johnny just smiling at me, licking his lips. I started getting that old feeling between my legs, before I realized what I was thinking. Mary was much bolder. She stood right there in front of them in her sheer bra and panties while she put on her bikini and adjusted it. Allen, Dan and Luke stood there adjusting the bulges growing in their pants. Mary just winked at them before I grab the curtain and closed it. “What are you doing?” I looked at her and wondered. “What happens when they find out who I really am?” Mary just winked and told me, “Don’t worry JOY.”   “Just follow my lead.”   We took our stuff to the counter, paid the bill, left the store and headed to the parking lot.


Dan was driving. We all piled into his custom van. I got in first and crawled to the back. Johnny was next and he slid in next to me. Allen called for the co-pilot seat and Mary sat between them on the bench style seat. Luke kneeled just behind them.


As we drove off, Johnny started to talk to me. He told me how cute I was and that he couldn’t believe I was just thirteen. I smiled back and wondered what was behind that bulge he kept adjusting in his pants. Mary turned around and asked if I was alright. She told Johnny to behave and that I was a good girl. “That’s what I hope,” he shouted back.

When he turned back he looked me straight in my eyes. I just smiled. He leaned over and held me in his arms and kissed me. I melted in his arms and greedily kissed him back. His tongue crawled into my mouth. I sucked it down my throat. At that moment I thought that’s not the only thing I want in my mouth. As we kissed, I reach over and rubbed his bulge. His cock felt like a snake crawling in his pants. While I rubbed him, his cock grew in my hand. I had jerk off a few guys by that time but what I was stroking was, by far, the biggest piece of man meat I had ever touched. We broke our kiss; I whispered in his ear that I only wanted him. I told him that the other guys could have Mary. That’s what she wanted anyway. He looked me in the eye and said that he had told Mary that he wanted me and that she could play with the others, if she wanted. However, I was his for the day and maybe the day after and after. When he finished I grabbed his head and sucked his tongue back into my mouth. He started to stroke my legs; but as his hand inched closer to my boy clit, I pushed it away. “I’ve started my period,” I whispered. “Don’t worry Johnny, I won’t leave you needy.” “You are so hot,” is all he said. With that, we both turned to see what was going on up front.


Dan was trying to drive. His attention was being distracted. Mary, her head laid back against the seat, was totally naked. Allen had his head in her lap and was licking her pussy. Luke had reached over the seat and was squeezing her big tits, pinching her large nipples while licking the back and side of her neck. Mary was starting to moan. I started to get jealous. I was ready to jump up when Johnny undid his pants and my attention was diverted to the most beautiful, 9 inch, cut cock I had ever seen. I look at it and then at him. “Touch it, JOY,” Johnny whispered, “Show me, that you like it?” My gaze fell upon his pork sword. I was momentarily hesitant. I thought to myself, there is no way I can handle this monster. A moment later, all my doubts were gone. I reach for it, grabbed it and lowered my mouth to lick a drop of pre cum lounging just outside its den. I kissed his head. I swirled my tongue around that bulbous head. I grab the shaft and slowly pumped it as my mouth surrendered to its invasion. I couldn’t swallow it all. I could barely suck a little more than half of its length. I remembered what I liked; how Mary had sucked my cock earlier. However, this was different, this was my man, my special prize for letting Mary dress me up as a pretty young thing; but it was more than that. I was a girl in love with a DICK! I knew that this wouldn’t be the last time I would feel this way.


Just then, there was a loud scream up front. Mary was coming as she knelt on the front seat. She had risen up from Allen’s hard tongue. She replaced it with his dick. She had leaned over the front seat and was sucking Luke’s dick. He had her bobbing up and down on his dick, taking it down her throat. His piece of meat was a good six inches. I knew Mary was having no problem with that one. I couldn’t see Allen’s hunk of stuff but the way Mary was acting; it must have been quite a whopper. Johnny was slowly playing with my prize, as I continued to watch the show. I could barely see Dan but then I noticed his right shoulder moving at a steady pace. He must have been driving with his left hand because he was fucking “Rosie” with his right. I giggled and turned back to Johnny. I kissed him soulfully. We broke and he told me how much he enjoyed watching my fascination with the orgy up front. “Don’t fear my stud,” I spoke with authority. “I have all I can handle right here with you.” I lowered my head again I replaced his hand with mine. I relaxed as I opened my mouth and let all 9 inches slide in. I was soon nudging his two big orbs with my chin.


I was in love. I reach around and found the crack of Johnny’s ass. I pulled him harder to my mouth, so as not loose my king size cock, I stuck one, then two fingers into Johnny’s asshole. He seemed to be familiar with this pleasure because when I found his prostate and pushed on it, his reaction was like a dam breaking; my mouth and throat were flooded with his thick, white cream. It tasted like nectar. He just kept coming. I swallowed till there was none left. Yet, I kept my mouth around his pole, feverously licking its head. Johnny cried out as his body spasmed and deposited another load of cum into his personal repository. As his seed dripped from my chin, I arose smiling in contentment. Johnny opened his eyes, hugged me and kissed me with a passion I had never known. We shared his cum cocktail. He looked at me and told me no one had ever given him an orgasm as strong as that one. He asked me, “Are you really thirteen?” I smiled, nodded my head and kissed him on the cheek. “I hope today is not the last time we are together this summer?” He pleaded. I just smiled and said, “Johnny, we still have the rest of today and tonight together.” “You may grow bored with me?” My eyes sparkled. I looked at him with lusty eyes. He said, “I don’t care if you’re only thirteen, you more of a woman than any I’ve met.”   I kissed my finger and put to his lips. “SHHHHH, you’ll be surprised, My Love!”