Lipgloss Dreams Ch. 01

I suppose that my story starts in the same way as a lot of other crossdressing boys with busy real lives: year after year of bottling things up, slowly buying clothes, dressing furtively, shamefully, until things would get too serious with a girl, then - a fearful, hurried purge, a headlong plunge into the cold waters or normalcy. What a deceitful plunge it always was! Eventually, I would tire of the girl, or she would tire of me, and I would again be free to face the world, still possessed of my desire to dress like a pretty girl, with only the memory of all the silky nighties and high-heeled pumps I'd ever owned, to ruefully contemplate having tossed aside.

I had lived this way for a long time. Too long. When I broke up with Lindsay four months ago, the cycle had begun again. The morning after I told her that it was me, not her, I looked in the mirror and contemplated the forming lines in my face. I wondered how I'd gotten so far in life without ever being true to myself. Twenty-seven years old, and I was still a scared little girl inside. I'd never given a chance to those feelings, never reached out for another girl like me. That was the day I decided I could no longer live that way. That was the day I decided to shave my legs for the first time...

Two days later, I was completely smooth. Well, except for the maddening itching everywhere. It was almost unbearable. It might have been completely unbearable, except that I had never looked so good in a pair of thigh-highs and a nightie. Every time I stood in front of the mirror and admired my black satin-covered boy-curves, I knew that I would never settle for hairiness again. I would never give in to the fear of being scorned or mocked in public again. I was going to be the girl I wanted to be. But I had to find someone to share it with. I didn't know what local bars a girl could go to. So I did the first thing that came to mind: a personal on Craigslist! This is what my ad said:

27 year old crossdressing boy, seeking another crossdressing boy for lipglossy kisses & more. First-timer here, just looking to explore, and learn about the horny, sweet girl that's been trapped inside of me all these years. Write soon!

xoxo

Kali <3

I thought it was the cutest, sexiest thing. The teenage girl inside of me was finally going to start living the way she wanted. Or, so I thought. The initial response was quite underwhelming, to say the least. Hairy boys in panties, non-dressing factory workers barely able to communicate using the English language, creepy looking elderly queens with sagging arms and cocks that looked like they couldn't be propped up with a tent rod. And the bots! Lord! I hadn't expected great results, but I thought I would find someone like me. But I tried to remain undeterred. I continued to renew my ad, and spend the spare parts of my paychecks on heels and lingerie and makeup, and practiced and tried to refine all of it. Which brings me up to last Saturday. That was the day I received an e-mail from Alex.

Alex's e-mail was short but sweet, and as far as I could tell, absolutely dripping with candy-coated sexual desire. It said:

Kali,

Hi! My name's Alex. I caught your ad, and you sound like just the gurl I want to meet. 24 year old CD here, also inexperienced, but I don't want to stay that way (; Hit me back!

Kisses,

Alexandria

Not much to it, right? But it stirred something within me, hard, and as I looked up from it, I realized that my boy-clit was standing at full attention. I had to talk to this gurl! I wrote, and she wrote back, and I'll spare you the details, but two days later we were on the phone, cooing to each other desirous things. At the end of that call, we made a date for the following evening. She would come over to my place, and we were going to just relax and be girls together. I was so excited!

When my doorbell rang Tuesday evening, I was filled with butterflies. I opened the door, and there she was, just as cute as her picture. I invited her in, and as she stepped into the soft light of my living room, I could see that she had put on just a little makeup. Her eyelashes softly glittered in the light. She smiled at me, and all I could do was swoon. If this was what it was like to be a pretty girl in love with other girls, I wished that I could have been doing it years before.

Alex was dressed androgynously when she entered. Cute, tight jeans with flared legs, and a swoopy, sequined top, under a black pea coat. I was in a white Abercrombie track suit. We poured ourselves rum and cokes, and agreed it was time to change.

Stripping down, giggly, we soon found ourselves in our bras and panties, and not much more. She looked very cute and innocent, with tight, perky breastforms. I'd made the mistake of picking D cups, and I thought they were too bulky for my frame. But Alex didn't seem to mind, as her pretty blue eyes flashed from my chest to my face, smiling at me. She slipped on a lavender kimono, and rolled her nude stockings up her slender legs with great deliberation. She knew just how mad with lust she was driving me as she did so. In fact, I think she was driving herself mad with lust too. I couldn't blame her. I wanted nothing more in the world than to explore that girl at that moment. But yet, we held off.

She topped off her sexy little ensemble with a pair of white, fluffy platform slippers, like a girl might find at Frederick's of Hollywood. For my part, I slipped on a black VS babydoll, with white lace fringes, and my black, seamed thigh highs with a reinforced heel and toe. I picked my pink, strappy, five-inch pumps, and let my naturally long light brown hair fall silkily over my shoulders. As I tied it all together, Alex touched up her makeup. More lavender lip gloss, and eyes that were more dangerous and more seductive. As if she needed that.

Alex knew I needed help with my makeup. She'd been doing hers for longer than I had mine, and she looked genuinely pretty in it, like a real girl. I felt that my efforts were still a little, um, clumsy, and I happily deferred to her skilled hands. We stood there, standing closely in front of the mirror, giggling and chattering, just like two pretty young girls getting ready for a night out. I wondered if real girls ever felt that way for their friends as they got ready. I was so full of lust for the girl next to me. She knew it, too, as she smiled at me and skillfully shaded my eyelids, making my lashes beautiful and full like hers, my skin even and shimmery, my face full of life.

As she finished, I grabbed the pink lip gloss I loved so much, and swabbed the applicator across my full lips, puckering them together with a soft, lustful pop. I looked at Alex, and she looked back at me, and I was filled with butterflies. It was that same wonderful feeling that you get at the top of the first hill of a roller coaster, that heavenly second before the gravity pulls you back down into the torrent of twists and turns and thrills. That's how I felt as we looked at each other, and slowly began to inch towards each other for our first lesbian kiss.

Words can hardly describe the electricity of that moment. Two girls, warmed and excited by all the closeness of the moment, the accidental brushes of body on body, the girlish giggling at tensions unspoken, and the heart-stopping lust that couldn't help but fill us both when our eyes would meet – it all crystallized with that first kiss. I remember my eyes closing, heavy and sticky with the girlish garnishment of mascara, my right hand slowly searching for and finding her slender waist, and the fingertips of my left, meeting her own fingertips, and then slowly interlacing. Our lips met, so very slowly, so we girls could savor the slippery sweetness of glossy lips on glossy lips, gliding together, lavender and pink swirling together. Her lips tasted so sweet.

As her lips parted for mine, our tongues met and we tasted each other's fullness, our sweetness. It was one of the most erotically moving moments of my life, to finally know the unbridled lust of two young women, no longer kept apart by the drone of real life, but instead activated and ignited by the dreamy realm of fantasy cross into reality. Our lips now pressed fully together, our tongues swooped and soared like lustful birds in flight. We drew our bodies together, as if hers sought refuge in my embrace. While we held hands tightly, lovingly on one side, the others ran up and down each other's bodies. We were lost in each other there.

After what seemed like an eternity, we broke the kiss and opened our eyes. It was truly soft and feminine and beautiful to see her there in front of me, eyes sparkling with desire, lipgloss smeared lustily across her full, loving mouth. I wanted everything that this incredible moment had to offer. I smiled as I intertwined my fingers with her, and led her to my bedroom, turning her around so that her legs were against my bed, and I was only a few, taunting inches away – smiling desirously. I pulled her close with my left hand, and began to lay a trail of sticky kisses across her artfully made cheek to her ear, while my right sought the front of her kimono and hastily went inside, searching for her femininity.

I found her there, engorged with lust, and falling out of her lace panties, her length rigid and hard, yet the skin soft and dewy. I began to stroke her beautiful length as I sucked sweetly on her earlobe. I felt and heard a lascivious moan escape her lips onto my neck. The heat of her breath and the softness of her clothes falling onto my skin drove me wild with feminine lust, and I stroked her beautiful length faster and more wantonly. I felt a viscous drop of satiny pre-cum ooze out of the tip of her beautiful cock. I needed her inside of my mouth, so badly. I gently nudged her onto my bed, and she slid back to make room for me.

I prostrated myself before her on the bed, and drew the sides of her kimono apart as I bent forward, placing kisses like rose petals down her smooth front. Then, there I was, with her beautiful length in my face, thickened with desire. As my hands played with the scratchy-silkiness of her nyloned inner thighs, I placed my warm lips on the beautiful plum-head of her sex. She gasped and arched into me, and I savored every sensation as I for the first time took a cock into my mouth. I adored this beautiful, engorged penis.

One hand helping to guide her, I slowly slid the length of her shaft into my mouth, trying to handle the wonderful fullness of it all. She tasted unlike anything I had ever tasted. I was tasting her - her truest femininity. I basked in this knowledge, and pushed my bubblegum rump up into the air as I took her in as deeply as I could. I felt her dainty, long fingers running through my hair, imploring me and encouraging me, as if that were necessary at all. I released her length, and allowed my plump lips to slowly drape as they receded along her shaft, sucking inward, imagining the soft, melting sensation she would be feeling down the shaft of her amazing cock.

Slowly, deliberately, I worked my mouth up and down Alex, faster and faster, with more and more desire. Her purse and balls filled my right hand as I slowly massaged, the velour warmth adapting to the shape of my lovingly cradling hand. Her plump cock head was the focal point of my every slurping gasp, from the point when it was deep and full in the back of my throat, to the shallowest point, when my lips sealed perfectly against the curving rim of her mushroom head.

At that moment, I felt more perfectly feminine than I ever had in my life – not even my wildest fantasies could have prepared me for this erotic tableau that was unfolding now. As my mouth sheathed her amazing prick, I felt so alive! Not only could I feel her pulsing inside my sumptuous mouth, but I was acutely aware of the exact form of my feminine body – on all fours before her, smooth legs cool on the top of my soft bedspread, nyloned legs rubbing scratch-silkily together, crossed at the ankle, the weight of my pumps knocking together with each lustful bob of my cock sucking head. The warm silkiness of my babydoll covering my body, the taste of lipgloss smeared from lips to rigid cock and into my mouth again – oh! How it drove me mad with carnal passion!

Clearly, it was driving Alex mad, too, as she moaned my name, telling me what a wonderful cocksucker I was, imploring me to suck more and more. And, of course, that I did: I savored the way her beautiful heavy length slid through my lips, into my mouth, and into the back of my throat. She filled me. Gratifying her was in turn the most gratifying thing that I have ever done for myself. I could feel her nearing completion as I suckled and bobbed, indescribable tremors that began to surface from deep within her, becoming stronger and stronger as I made love to her with my mouth.

As I felt the strength of her orgasm ripen, I began to vary the intensity, pausing at the deepest point, both to enjoy the feel of her within me as well as to allow her to enjoy the velvety sensation of fucking my face. Again and again I slid her length in and out of my ravenous, glossy lips, until I felt her nyloned thighs tighten in a new way around my head. I dived in again and again, and her legs became tighter and tighter, and she encircled them around me, linking her ankles at the small of my back.

Alex began to come as I was near her shuddering, thick tip. I closed my lips tightly, and felt a hot, slippery jet of her spunk erupt into my mouth. I closed my eyes and sucked, wanting to draw every amazing drop of her out and into me. It seemed to last forever, though it could have only been a short moment. I opened my mouth and released her from my starved, feminine lips, only to have another rope of her delicious semen splash across my open mouth, and across my made up face. I felt painted with her salty beauty, filled with her. Again she throbbed, and one final, small spurt arced up and into my open mouth. I was in heaven.

She released me from the embrace of her legs, and I swallowed the jism that filled my mouth. I opened my eyes and scooped a glob of delicious cream from my cheek with my finger, and smeared it across my lips, savoring the way it mingled with the electric slipperyness of my spit and lipgloss. I looked up at her, and saw her craven eyes beckoning to me. A smile played across my cum-frosted lips as I crawled up to her, and again we kissed, sharing the spiciness of her sweat cream between soft mouths and intertwined tongues. When we had devoured all that was on my lips, her soft mouth tenderly, eagerly cleaned the rest of her delicious mess from my face, and again we kissed, our girlish mouths playfully wrestling over every last drop. We smiled at each other, giggling.

I collapsed next to her, and we lay there for a few moments, not talking, but simply savoring the tremendous explosion of lust that had just occurred. Her hands roamed about the silken sinews of my body, as mine likewise explored her curves and crevices. We kissed once more, mouths full but lips closed, as her own hand found the nexus of my legs, where my passion lay, still engorged. As the kiss broke, we looked again at each other, smiling. Almost imperceptibly, she began to move in the direction of my desire. My heart and my loins rejoiced in the knowledge that our incredible night of girlish lovemaking and exploration had only just begun.

(To be continued...)