How I Met My Boyfriend

by Anielle Cherte

 

First of all, I am a crossdresser. That is, I have a man's body, more or less, though truthfully, my long thin form and fine features are more suited to feminine than male appearance. Anyway, from my earliest days I reveled in every instant I spent in female clothes. Oddly, I was never an effeminate man, and I was expert at projecting my male image, and diverting attention from my feminine self. My feminine nature, exquisitely sensual as it was, remained private and hidden, but very much in control, the woman behind the man. At times, she playfully allowed select individuals a quick glimpse of her, shown in a sudden, elusive, glance, or turn of the head, glowing facial expression, or rhythmic body movement. She delighted at being nearly noticed, before she quickly hid back behind my masculine facade.

Actually, her appearances were seductive whispers in my own ear, letting me know that she was hot for a good session of dressing and creative self-expression. That day, or night, or as soon as possible, I would be enjoying the pleasures of time alone, dressed, and fully aware and in touch with the girl that was more me than any guy I or anyone thought I might have been.

This was my life, for years, for decades. I was comfortable with Ani (by now, I'd learned, and she'd earned her name). At times, she seemed more a wife than a part of me; the dichotomy had grown and defined itself. She was happy with the time I gave her, though sometimes, I and she knew a longing in her heart.

I had the life of a man, and that life paid the bills, and provided the means to keep on living. I was willing, though, as a man, to risk giving up some territorial safety zone to allow Ani to try coming out. Ani, however, was content, a bit afraid, and completely unwilling to take the steps that could easily lead to so much trouble. She stayed inside, hidden, but still a bit playful. She'd let herself be seen for a fleeting instant by a man, a stranger, perhaps, or a friend, then quickly retreat, watching for his reaction.

Oddly, I had gotten a few come-ons through the years from men thinking I was gay. I was not gay, and I was not open to the passes of gay men. They did not turn on ani, nor was I.

Still, there was something unresolved. There was a longing.

"It's very odd to say, but I sense a feminine nature in you, and find it alluring," my friend from work said to me over a drink at a bar. I sat listening, Ani over my shoulder, and for a moment, she emerged, and took over my whole body. After a silence, my friend changed the subject, and we drank and talked about baseball and work.

That night, Ani troubled me in my sleep. This had been the first time anyone had spoken to her, and she couldn't get over the thrill of having been called "alluring."

Everything was normal the next day at work, except that I was very tired from my night of fitful sleep, and that Ani seemed intent on taking advantage of every nodding moment to slip excitedly out. It was rather remarkable, seeing the office, and experiencing my daily humdrum chores from Ani's point of view. Having not seen my friend throughout the morning, I strolled, at Ani's insistence, in the afternoon past his cubicle. When I saw him, I actually felt Ani take over my entire body. Ani greeted him, with a voice and manner more hers than mine, my face combining Ani's excitement and my embarrassment. My friend perked up with a smile that was clearly meant for Ani. "We'll have to do beers again soon," he said. Ani smiled.

Life was a bit chaotic the next few days. Ani's excitement and anxiety were constantly present. I felt like a woman in man's clothes as I struggled through every hour. I had seen little of my friend, other than a few furtive glances. Finally, on Thursday, he approached my cubicle. "Tonight?" was all he said. "Of course!" Ani answered.

For the first time in her life, Ani was going to meet a suitor. She was as calm as she was nervous. She was focused. When she entered the bar, my friend was already there. He saved her a seat, and she slid right into it. Ani was very much aware that my friend was looking right at her, as he ordered the first round, and laughed his way through the small talk. I played the role of drinking buddy, and Ani sat quietly watching, enjoying that she was the secret guest of honor.

Finally, halfway through our second beer, I spoke up. "Last week you said something." My friend quietly looked into his drink. "Normally, I wouldn't comment, react, or maybe even think about such a thing," I went on, "but it caught my attention that you sincere and open, and daring enough to say what you did." My friend looked at me, smiling gently, warmly, as he listened. I felt shivers as Ani moved inside me; my lips became her lips, and she smiled charmingly as I spoke. "I have to admit something..." Ani shifted in her seat, "I want to admit something, to you..." I turned and looked at him. He looked into my eyes; Ani's eyes sparkled. "I do, very definitely, have a feminine side." My friend smiled broadly, "yes, I know," he said, "and I feel that she is here with me now." Ani felt chills; she sat motionless, not knowing what would happen next. I felt a bit apprehensive, hoping that my woman and my friend wouldn't put on too public a display. The world, after all, could only see two men, and I was recognizably one of them.

"I enjoy dressing," I blurted. My friend's smile turned to grin, "and I would love to see you," he said simply. He turned toward his beer, and his hand brushed my arm. It was a pleasant sensation, being touched so gently. "Would you like to tonight?" I asked, invitingly.

Like a gentleman, my friend paid the tab, then, I felt as if, he escorted me to the door. I gave him directions to my house, and he said he would follow. We extended our hands to shake, but I experienced it more as holding hands. He said he couldn't wait, and slid into my car, fumbled the key into the ignition, started the motor and sat feeling the air-conditioning on my face as I waited for him to pull up in his car.

I invited my gentleman friend in, showed him to the living room, got him a drink, and asked him to be comfortable and patient. Then I excused myself to tend to my dressing.

I'd given a lot of thought over the past couple days about what I would wear my first time being seen; I had it figured out from skirt and top, through stockings and heels, to panty and bra. I knew well from years of dressing that my legs were my best asset, and that a short, tight skirt was the best way to highlight them. I chose red, which seemed to highlight my hips and ass, at the same time contrasting well with my shear black thigh highs, which I knew to add the sexiest shade to the length and contours of my legs, and leaving that oh so sexy bit of bare skin leading up under my skirt. A tight knit top, black, which seemed to make my already thin waist and torso even more feminine and petite, all the while adding interesting shadows to my slightly augmented breasts, long sleeves, which made my arms look even longer and more delicate, and open shoulders, which allowed for just a hint of cleavage, while making the rise to my long neck even more inviting and providing a nice ledge for my long blonde hair to play on. I knew my dressing routine well, and excitedly rushed through it.

In the bedroom, I got everything out, laying it on the bed. I stripped out of my drab clothes. Naked, I rubbed my hand over my face, and felt a bit of stubble. I rubbed my other hand over my legs, and smiled at their smoothness—I had shaved them in the morning, as I'd done every morning for the past several years. I pranced for a moment in the mirror, admiring my sunless tan. I splashed lotion on my face, and shaved carefully and thoroughly, then rubbed in moisturizer. While waiting for the lotion to soak in, I gave myself and enema, then I slipped into my low rise black rayon panties, taped on my breast enhancers, and fastened my pushup black bra. I pulled the knit top over my head and arranged it properly over my bra. Returning to the bathroom, I sponged on a thin coat of foundation, a light brush of blue shadow to my eyelid, mascara and lashes, stick on red nails, then my favorite bright red lip gloss. Back in the bedroom again, I slid the thigh highs ont my legs, and slipped my feet into my four inch red patent heels. Then came the skirt. I loved working backwards like this, and stepping into my skirt while already in heels; it seemed to challenge my feminine poise. Finally, looking in the mirror, I lifted my favorite, longest blonde wig up over my head, and put it on. I felt stunning! As I looked at myself, my body animated itself, as it normally did when enfemme. This time, however, I tingled with excitement knowing that Ani was about to step into the world of womanhood.

I entered the living room. My suitor stood as he gazed at me. I was as nervous as I was excited. I walked into the room, stepping back and forth in my heels, aware that I was modeling myself and my clothes, and reveling in my man's obvious appreciation. We met in the center of the room. He extended his hands, I took them. "My!" he said, "you are more beautiful than ever I could even have imagined!" I was just smiles and grins, loving the way I felt, and the way he was reacting. "We've not been introduced," he said, "your name is?" "Ani," I quickly replied. "Ani," he said, "of course," like no other name would fit. I smiled; this man knew exactly how to treat me, and how to play to me. His hands moved to my hips, and he pulled my to him. I looked straight in his so very close face, "and your name, sir?" I felt that, as Ani, I'd really never met the man, till now. "Tracy," he said, and he tilted his head to kiss me.

We kissed for a long time, our bodies close and tight, our hands roaming all over each other. I couldn't believe how good it felt. Our tongues played with each other's, then he pushed his deep and hard into my mouth. While pleasuring my mouth with his tongue, he guided my hand to the rock hard bulge in his pants. I breathed heavily, and sucked hard on his tongue. He pulled away and looked at me. I knew instinctively what he wanted, dropped to my knees, unbuckled and unzipped him, pulled down his jockeys, and watched wide-eyed as his hard cock emerged before me. I looked up at Tracy; his smile was sweet, loving, and desirous. I opened my mouth wide and took him in. The scent and the taste were intoxicating. I quickly lost myself in long strokes up and down his shaft. I pursed my lips over his head and sucked hard. I heard him groan, and my head began to bob up and down on his cock. Then I worked his pants down, grabbed on to his cheeks, and pulled myself all the way on to him. His cock popped into my throat, I gasped, nearly gagged, but worked into a strong convulsive rhythm around him. His moaning turned to agonizing shouts, and he pulled me off him, and in the same instant fired a strong stream of thick white cum. I took as much of it as I could into my mouth. The taste and the feel was unbelievable. I swallowed again and again. When he stopped, I licked the last remaining drops from his cock, which brought about more moans. Tracy dropped to his knees, kissed my madly, then fell on his back to the floor. I as first sat beside him, holding his hand, and touching his contracting cock with my fingers and nails. Then I got to my feet, and stood for a moment, realizing what had just happened, and feeling totally happy about it.

I walked around the house, feeling totally happy, sexy, feminine, and proud. After a while, Tracy got up, too, and came to me. "Thank you so much, Ani," he said, hugging me. "And you don't think that was good for me, too?" I asked. "I hope it was," he said, "but I want to do so much more for you, that I'm very certain you'll find…satisfying." His hands held my ass; my heart beat. I looked at him; there was nothing to say. I wanted very much what he was offering. I needed it, and couldn't wait. I felt my ass come alive in his hands, and he kissed me. "Bedroom or living room?" he asked. "Bedroom," I answered, and led him in.

Tracy sat on the bed. I took off my skirt and top. He looked at me and gasped. No better reaction could a girl have from a suitor in her boudoir? I strutted around; he stood up. We embraced. He laid me down, and took off my panties. I raised my legs. He mounted me.

It was the greatest sexual experience I'd ever had. His hot cock circling my ass completely turned me on. My hips raised and strained and rotated for him. His tip found my anal lips. "My cock and your pussy shall be best friends forever," he said, and he pushed into me. I nearly passed out from the first thrust. A shivering sensation spread out through my body from head to toe. When it reached my brain, I flushed into a level of ecstasy I'd never known. My body began moving. My hips began thrusting violently against his. His cock inside me seemed to touch ever nerve. I screamed; I howled. My body heaved and contracted. My arms flailed about. My legs wrapped around him, and pulled him in deeper and harder. I came. I came with an orgasm the size of the universe. I floated indefinitely in space, and when I drifted back, he was still fucking me. I went in and out. Orgasm, after orgasm, after orgasm. When he was done, every cell in my body was singing. I was out of body when he came; I saw it from above. When I snapped back into my body, I was howling and humping, he was howling and humping, and I squeezed while he pumped every last drop of cum into me.

Needless to say, a performance like this demanded many passionate encores. Ani and Tracy became regular lovers, and their relationship blossomed in every facet of their lives. Finally, Ani became the rightful, dominate personality in my life.

  

  

  

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