"Mmmmmmmm," I cooed, letting Charlie know that he had made me the happiest sissy in the world (or at least in the southern United States).
"You enjoyed that didn't you baby!" Charlie stated.
"Yes.. yes I did very much so!" I responded, "I have been waiting for that for a VERY long time!"
Charlie and I had met on the Internet a few weeks before, me a repressed sissy living in the Bible belt, Charlie a man that knew he liked girls like me. Our union was destined to be one that would written about, since I decided it time to come out of the closet I thought I should be the one to let the world know that I am a man that prefers to be a woman.. at least in bed!
Charlie had already taught me the joys of sucking a cock, and I would be forever grateful to him for bringing me out. Now I was ready to be deflowered like so many real girls get to experience during their teenage years, but for me as a cross dressing sissy I have had to wait until my thirties for this exquisite experience.
Charlie helped me back to my feet and on wobbly legs led me to the full-length mirror in his bathroom. With his arms wrapped gently about my waist, Charlie showed me what I looked like following my first womanly sexual experience. I saw drying trails of his cum all over my beautifully made-up face, and beneath that I could see the radiant glow of someone who is very happy with herself.
"You look gorgeous babe," Charlie told me.
"Thank you, sweetie," I replied, "I feel so feminine, so right for the first time after sex. In the past I never knew what to do or say after sex with a woman. But after this I know exactly what to do.. Thank you, Charlie.. Thank you so much."
"I am just glad you enjoyed yourself. Neither of us knew what your reaction would be, but I think we are both grateful that your response is favorable," replied Charlie, "You make an incredible woman."
Then he lightly kissed me just behind the ear. I melted into him then, pushing my virgin fanny into his crotch, willing him to take my virginity.
I slid my right hand behind me and wrapped my fingers around his manhood. "We need to get this hard again, baby," I breathed.
"Are you ready to be fucked my pretty little sissy," demanded Charlie.
"Absolutely ready!" I exclaimed.
Charlie led me back to his bedroom. Gently laid me back on his bed, and then began kissing me. He took my hand and placed in on his cock, I knew that I must use my feminine wiles to get him erect again. As we kissed I slowly stroked him, running my nails up and down the shaft gently. Then Charlie slowly raised my skirt tickling my silky thighs with his manly fingers. Charlie slid his hand between my thighs and my legs parted like a flower opening for the first time in spring.
"Are you sure this is what you want baby," asked Charlie.
I had never been so sure of anything in my life. I knew for the first time what I was and what I was meant to be!! I am a queen, a sissy, a woman wannabe.I am a toy for a man's pleasure!
"Yes, baby, I so want this and I want you," I moaned.
Charlie slid off the bed, moved between my thighs and slowly slid my virgin white boyshorts (I know.I know), and lifted my thighs until my rosebud was where he desired. Charlie lowered his face and gently blew, his hot breath sent shivers through me. Then I felt his tongue gently flick against my tight virginal hole.
"Ohhhhhhhhhhh!" I squealed, "That is heavenly!"
Charlie showed me the joy of having my boypussy eaten. I squirmed and squealed and purred like a kitten. Charlie knew exactly where to place his tongue to give me pleasure, before long my thighs went limp and we both knew I was ready for my first man!
Charlie stood and his penis was rock hard again, and glistening with precum. He reached into a drawer and got a bottle of lube and worked some into my sweet ass, he asked if he should wear a condom. While I knew he should, and he was sweet for asking, I also knew that I wanted to experience this hot skin to hot skin for the first time.
Charlie placed the tip of his cock against my hole, biting my lip I took a deep breath and he slowly began to enter me, as my sphincter relaxed, and the last remains of my masculinity evaporated I gasped, and he stopped allowing me a moment to accommodate him. After a moment Charlie slowly slid in a little more, and a little more until he buried balls deep into me. It felt so good, so right!
Charlie began to increase his pace until he was ramming his cock into my asspussy and we could hear his balls slapping against me. I wrapped my legs around him and pulled him tight, he leaned in and we kissed. It was the most electric kiss of my life, kissing my man as his cock tickled my prostrate. Charlie told me he was going to cum, I pulled him tigh to me and felt his cock begin to twitch, and then felt his cum flow into my bowels. Torrent after torrent of his hot seed filled my ass and the warmth that spread through me is indescribable. Charlie collapsed onto me and we kissed until he became flaccid and slid out of my now well fucked ass with an audible, "POP!"
"How was it?" Charlie questioned.
Breathing heavily, I told him it was wonderful, exquisite, and the experience that I had been desiring for so long. I got up slowly and made my way to the bathroom my thighs shaking uncontrollably. I could feel globs of his cum sliding down my thighs as it leaked from my stretched hole. It felt so feminine to have a mans cum dripping down my thighs. I quickly shed my dress, pulled my panties back on, and slipped into white maribou trimmed baby-doll nightie.
I slid back into bed next to Charlie, and gave him a sweet kiss on the lips to say thanks and we drifted off to sleep in one another's arms.
I hope you like the story so far, I have enjoyed bringing my tale (or is it tail) to the world. There have been several since Charlie that I can also relate, if the audience so requests, I may reached at jenna_shannon2003@yahoo.com. As many of you may know, I have also experienced guilt as a result of my sexual leanings, these feelings are a real turn-on for me, and I get excited when I am reminded of being a sissy.
I look forward to sharing more, and I hope everyone has a very Merry Christmas!