"Dressing up"

*Inspired by Monica and Vanessa


I think I was in the second, maybe third grade that first time. I had an older sister very much into fashion, make up and designing. Her room always had a scent of perfume and was filled with all sorts of girly clothes and accessories. I don't know why, but I remember always being drawn to it. Wanting to go in and look around and touch things. I wondered what they felt like. Girls were so pretty, so feminine and always looked so cute. I wanted to feel that way, too. It was just curiousity. I remember being excited and searching through her dresser looking for soft, silky things to try on. Slipping on a pair of panties made my young body feel amazing. The way they hugged my ass and tightly caressed and held my balls and cock. I knew that boys didn't dress this way, obviously, but they felt so wonderful on and made me feel so beautiful. It kind of seemed natural, even.

Being alone for hours after school gave me pleanty of try things. First, I think I put on panties and a bra. I would roll around on ner perfume scented bed. rubbing myself on it. It felt so good, although I didn't know anything beyond that. It was just such a wonderful feeling. Seeing myself in the mirror, in lingerie, my young body even looked girly. As time past, I got more confident and more adventurous. Walking around the empty house, even going into the back yard. Walking around in tight, silk panties, feeling them rub against my cock. Too young to do anything, but I know it felt good.

It was another day like the others, only this day I did not hear a friend knocking on the front door. As I walked around inside I didn't notice him standing by the back yard patio door. He had gone back looking for me. I turned to the sound of knocking on glass and saw him and he saw me. I was so embarrashed! I ran to my room not knowing the door was unlocked. He came in and followed me, laughing, asking what I was doing. Quickly, I put on a shirt and shorts, but did not have time to remove my sexy panties. I don't remember all that was said, I think I said something like they just feel good. Maybe he asked if I wanted to be a girl, I don't know. Maybe he asked if I liked boys. But I think those questions were beyond our years. What I do remember though, is that we touched each other. Touching his young dick and him touching mine made me dizzy and made my head spin. It just felt so good, so natural. I think we were too young to get erections, but it felt amazing anyways. We even took turns putting our mouths on each other. Taking his small cock between my lips gave me the same euphoric feeling as when he did it to me. It was in a different way, one that I could feel, but maybe not understand. We shared two or three more encounters like that but no more. Somehow, we quickly drifted apart.

Gradually, after getting dressed up in silky, girly underwear, I experimented with her make up, too. Putting on red lip stick, maybe remembering how those lips sucked my friend's young cock. More wonderful, girly sensations. Trying on blush and eye make up. I had found some long wigs hidden away in a box among my sister's fashion stuff. I tried them on. I looked and felt so glamorous. Getti g older now, I even wondered if boys would find me attractive. This, of course, was all in the privacy of my house. To the outside world, I was just a normal boy, playing sports and curious about girls.

More time past and now wearing panties would make me so hard. Dressing up, even imagining sucking cock, it gave me the best orgasms. I knew more about sex by then and even started to pull my panties to the side and touch my asshole. Would boys want to fuck me? Just the tightest, little hole, it hurt but I liked feeling my finger inside me. It was easy to imagine a boy's penis pushing inside me. The thoughts turned me on must as much as girls did. But this was only a fantasy life until my first year of high school.

I had nearly forgotten about my young friend all those years ago, but then I saw him and he saw me. I guess he had gone off to a different school back then, but now we all went to the same high school. I remembered being young and curious, touching each other, sucking on each other, but did he? It was not long til I got my answer. I saw him walking towards me. As we walked and talked, with no one else around, he asked if I still dressed up. It surprised me, I guess I was defensive. I asked him, "Why, do you want me to?" My head swam at his answer, "Maybe." I knew the urges, the need of a young man that age, I had them too. Overwhelmimg, overpowering sometimes, the need for release.

Somehow, through my nervousness, I asked if he wanted to come over sometime. We agreed to meet after school. I couldn't concentrate tne rest of the day. Sitting in class, my mind would drift, wondering what might happen later. Everytime, I would get an erection. By the end of the day, I was ready to explode. I remember practically running home. Nervously, I waited and soon heard a knock. I invited him in and told him where my room was, he said he remembered. I think he even smiled. By this time, I had stashed away some Playboy and Penthouse magazines I had found, along with several girly outfits, wigs and make up I had collected. I gave him the magazines, knowing how horny they would make him. I went to the bathroom and got ready. First, sexy, girly, panties, then a bra. I had started wearing whole outfits and squeezed into a tight, form fitting, shlrt dress. I pushed my cock between my legs. It was difficult to hide in such a tight, sexy dress. By the time, I put on some make up and a long, flowing wig, my cock was dripping in anticipation. From the bathroom,I said, "OK," and stepped out. So nervous, but I felt so sexy. I imagained being a cute, sexy girl, wanting to please her boyfriend.

I stood in the doorway, thankfully he spoke first. "Wow, you look great!" I guess neither one of us knew what to expect or what reactions we might have. I knew that I liked the way he looked at me though. What a turn on. He sat on the edge of the bed, wide eyed, with a look of such young, eager lust. With more confidence now, I walked in and tried to swing my hips, trying to be seductive, trying my heighted his urges. I stood in front of him. I guess I had no idea what to do next. I knew what I wanted, must not how to start. He reached out and ran nis hand over my hip, then to my ass. He exhaled, his breath broken, he was nervous too, but nature and desires took over. He lut his other hand on my ass, cupping it and squeezing it. I felt so wonderfully girly and I wanted to do girly things. I knew he wanted me to do those things, also. I moved to my knees in front of him. Between his legs, my hands trembled as I reached for his waistband. So anxious to see cock, my eyes were glued to his crotch as together we slipped off his pants and underwear. Beautiful, swelling cock, bouncing and throbbing. I remember smiling and brushing my long hair from my face, tucking it behind one ear. I had dreamed of this. What would it be like, how would it feel, how would I feel? He layed back, already light headed, I think. Throbbing cock was more exciting than I imagined, desire welled in me. I put my lips to him, it was already better than I imagined. I pressed my lips to his smooth, tight balls and his cock bounced against his thick, dark pubic hair. My own cock was rock hard and wet, but I dared not free it. Instead, I kept it tucked in my panties as it throbbed against my ass crack. My mouth was eager for it, wet for it. His tip was glistening with pre cum as I held it, pointed it at my mouth and slid my lips over it. His taste, the sensation made my eyes roll back. I wanted to moan but was too embarrashed. I sucked his cock. Falling in love with how it made me feel. His breathing quickly quickened, I heard, "I'm gonna..." and felt the wonderful rush of his explosive orgasm. Cum and saliva ran down his balls. I made soft, "Mm, mmmh" sounds as I continued to suck him and feel his release. Draining his balls, I felt so wonderfully sexy, even satisfied. Moments later, he propped himself up on his elbows and looked down at me. His eyes looked all glassy like he was intoxicated. "I couldn't hold back," he said. I told him that it was ok and I rubbed the tops of his thighs before realizing that it might be a little too girly. Funny as that may sound now.

I so enjoyed looking at his cock. He was soft now, but still so alluring. I could see hints of my red lipstick on his shaft. A wonderful reminder that I had just sucked my first cock. The flavor of his semen, the way it made me tingle, it was all so incredible. The whole afternoon was just so incredible. After he left, I stripped out of my dress and layed down. Touching myself, my chest, over my bra. Rubbing the head of my cock, still stuffed inside my panties, wet and ready to cum. My body shook. With the flavor of cum still on my lips and tongue, I trembled and filled my panties with warm sperm.

A few days later, he found me at school again and asked if he could come over. "I'll just start askng if I can walk home with you," That was it, that was our sign. I knew immediately that I would be taking his cum again and each time he said it. I could not help but rush and smile as I got ready for him again. Nerves and fear where replaced with excitement and lust. He was standing this time when I walked in, his eyes washing over me. He turned me around and ran his hands along my hips. Hiking up my dress, he ran his hands over my bare ass. I had picked out a thong for him and feeling his hands on me, was so glad I did. Even through my long, flowing hair, I could feel his hot, lusty breath. He dropped his pants, I felt his erection press agasint me. I thought he was going to fuck me. I guess I realized then that he could do whatever he wanted with me. I guess I realized that it made me feel even more amazing and girly. I was quickly becoming addicted to the feelings.

Maybe he lost his nerve, whatever the reason, he had me sit down on the bed as he brought his hard dick to my ruby red lips. He brushed the hair of my wig back as I dove my mouth on him. This time I moaned for him. Playfully flicking my tongue on his tip, savouring the pleasure that his cock gave me. Taking him to the back of my throat, it felt so full and incredible, I felt his pubic hair tickle my nose. So erotic, so amazing! I grabbed his ass and sucked him. I wondered what he must think of me, it just seemed so natural. Again, his breathing quickened, so quickly. Was he going to cum again so soon? I sucked him, eager for my reward. He pulled away though. To my surprise, he gripped himself and shot his load at my face. I couldn't believe the power of it, the force! Stream after stream struck me and splashed against me. By instinct, I opened my mouth. It was just the most slutty, amazing thing. He laughed a little, I think it surprised him too. So much hot cum! It dripped down my chin and all over my dress. Nothing could be sluttier, I thought, and I loved it. I was in love with it. I stroked his dick and licked up his cum bedore sucking softly on his cock's head. That same light headed feeling washed over me, euphoria.

Another meeting and this time he went for it, truly making me a complete girl. Peeling up my dress and pulling my thong to the side, he bent me over the bed. Hands out, bracing myself, he pressed his hard. wet dick against my opening. I struggled to relaxed and then he was inside of me. I tried to muffle the pain, but it was thrilling. His hands on my waist, his fingers digging into me with need and urgency. Without thinking, I moaned out, "Yes, yes!" Thankfully, maybe regretfully, he came quickly, grunting and thrusting and filling me with his warm seed. When he pulled out of me, I felt it run down my legs.

I already loved sucking dick and taking cum, but this was something different. I was eager to feel him inside me again, I wanted him inside me again. Dressed up, going down on him, giving him head, he was rock hard. I didn't say anything, I never really did, I just got on the bed with him as he layed back. Facing away, I reached down and pinned my erect cock to my belly with my tight panties. Silly maybe, but I didn't want him to see it. I hiked my dress up over my ass and rubbed my crack along his stiff cock. Through his breathing, I heard him moan. Pulling my panties to the side, I took spkt from my mouth and rubbed it on my asshole. Labored, he said, "Yes." It was a turn on to know he was watching. He pressed on his shaft and pointed it. I felt his tip on my opening and it made me bite my lip. I exhaled and bit down and lowered myself down onto him. My asshole spasmed and struggled to open for him, slowly, wonderfully, I started to move on him. Feeling him deep and filling me, rubbing against something inside me that seemed to be directly connected to my balls and cock. Pre cum ****** from me. I grinded slowly on his dick and moved up and down. Knowing how quickly he cums, knowing how I had wanted this, I rubbed my sticky and slick cock's head and felt my orgasm build. Hard dick insdie me, orgasm building, I cried out and released, making my dress a hot, sticky mess. My hole squeezed down on him in waves and he released also, shooting his wondeful fluid in me. Silently, I climbed off him and pushed my dress down. I cleaned his cock, and felt his cum ran out of me. It was the most erotic feeling. Yet, there was another feeling, maybe a complete feeling. I got back next to him, brushed my hair clear and rested my cheek on his thigh. He stroked my hair, yes I felt complete. Laying there, I petted his soft cock and planted soft, even loving, kisses on it. I thought I might want to kiss, a for real kiss. It would be my first, but seemed so right. As his cock slowly began to swell again, I kissed up his chest, nervously putting my face back down on him. Again, he stroked my hair. I felt such urge, wanting to truly experience it as a girl. I gripped and squeezed his cock and lifted my head, quickly stealing a soft, gentle kiss on his lips. A first of many, they were such a turn on for me.

My cravings were increasing. My urges for his body were expanding. He had started to give me a little time to get ready beforehe would come over and I was ready. Dressed to the hilt, make up, lashes and full lips, I took his hand and lead him to the bedroom for privacy. I quickly dropped to my knees and eagerly took down his pants as he watched. I loved seeing his soft, hanging dick like this. Cock can be so gorgeous. I kissed it, I loved kissing it, but then turned around. My hands on his hips, I kissed his ass cheeks and pressed my face into him. I wanted it, he did not ask for it, but I hoped it would be a turn on. Firm, narrow and smooth, his little ass looked so sexy. He bent slightly, nothing like the pictures of girls that I had seen, his asshole clearly became exposed. Right there, just a little beyond his ass cheeks, the delicate folds of his hole. So sexy, there was no resisting, I held his ass and licked his hole. Immediately, I felt that amazing dizzy, intoxicated feeling. I lappped at and licked him and pressed my lips to it. Fuck, I remember moaning! I'm sure he thought I was his toy for pleasure and I guess I was, but this was for me! Fuck me, fill me with cum. Fuck my mouth, shoot your load down my throat, but this was for me. So kinky, so erotic and to me, so sensual. I hoped he couldn't see, but I rubbed my cock to orgasm as I licked him. It was just so wonderfully submissive and dirty.

There is still nothing that turns me on more. A normal man during the day, but night gives way to silky, lace panties and tight sexy dresses. Getting ready for a man is simply the most thrilling thing ever. My cock leaks at the thought, creating lust, satisfying men's needs. Each and every time, I can't wait. What will the night bring?
Published by PaulMayer00
8 months ago
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10
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vickiep
vickiep 6 months ago
Would love to witness this. 
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emmersonsprite
emmersonsprite 6 months ago
Hard as a ROCK reading this !!
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PrivatePersonality
PrivatePersonality 7 months ago
One of your best yet!
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redclay56
redclay56 8 months ago
Love these tales of burgeoning awareness and yearning...
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Vanessa718
Vanessa718 8 months ago
to PaulMayer00 : Why thank you hon!
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PaulMayer00 Publisher 8 months ago
to Vanessa718 : It was meant for you, my love. Also, for Monica who wrote a story in your favorites on your page.
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Vanessa718
Vanessa718 8 months ago
to PaulMayer00 : Who’s Monica and Vanessa?
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dmf399
dmf399 8 months ago
So wonderfully erotic.  The feelings expressed are spot on, so real.
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PaulMayer00 Publisher 8 months ago
to Vanessa718 : I just added a little more. Hope you saw the "Inspired by" line. 
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Vanessa718
Vanessa718 8 months ago
Such a sexy coming of age story!  The irresistible urge to give in and finally please a man.  There is nothing else quite like it ever darling ❤️❤️
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