Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I’d seen him and it seemed like fate that after all that time, I ran into him the first night I finally gathered the courage to go outside of my home as ‘Katie’ instead of my normal, everyday self of Kyle. Back then, we had hung out together quite a bit, but always in a group, and never alone with each other. I had never admitted to myself how turned on I felt inside whenever we would play basketball with the guys. He always thought I used to guard him so close for defense, but in reality, I had loved the feel of his sweaty body continually bumping and rubbing against mine.
Todd held me from behind while he whispered softly in my ear, “Say it out loud, Katie. Tell me what you want.” I could feel his hot breath flow lightly along my neck and earlobes. I was so turned on that it was impossible for my black and purple silk panties to contain my cock any longer. It seemed like all the blood in my body had rushed to fill its veiny length and had taken less than a few seconds to become fully engorged.
My knees were weak as Todd caressed my breast inserts with one hand while pulling my ass against his crotch with the other. I could hardly stand up in my stiletto pumps as felt his erection pressing through the thick fabric of his jeans. The rough denim felt great on my bare skin by itself but the thickness of his hard cock rubbing along the length of my ass crack is what really had me excited. I couldn’t remember the last time I had been so turned on. Of all the guys I had a crush on when I was younger, Todd had been at the top of that list. Now, nearly a decade later, here I was with my skirt pushed up against the front of his jeans.
As Todd whispered in my ear, I closed my eyes, took a trembling breath, and finally leaned against him, hard. I pressed my ass against his crotch and in my best feminine voice said, “I want you to turn me around and gently push me to my knees as you slide your cock into my mouth and down my throat. I want you to shoot your cum in my mouth and then kiss me like I’ve never been kissed before as we share your cum between us. I want you to turn me around again and bend me forward so I’m resting on my knees and chest. I want you to pull my silk panties down my legs so they rest at my ankles. I want you to slide your tongue in and out of my asshole until it’s relaxed and lubed. I want to feel your hard cock pushing against my hole as I raise my ass in the air and I want you to fuck me like the little sissy slut I am. I want you to bury your cock as far into my ass as you can and shoot your load deep inside me.”
I looked down at my feet and quietly whispered, “That’s what I want.”
In all the years that Todd had known me as Kyle, I’d never admitted that I liked to wear women’s clothes. In the years since, I had spent a lot of time learning how to dress, how to wear heels, how to walk, how to act, and how to apply makeup for the desired effect. There had been only one effect I had been going for with tonight’s makeup choices and that was “fuck me, please”. My eye liner was thick but not too thick and curved around my eyes just right, ending in a little cat-like feathering at the edge. My lipstick was a luscious shade of what I like to call “muscle car purple”. It’s a beautiful color and personally, I think because it reminds guys of their dream cars, they can’t resist it. My hair had been growing out for a few years and was luxuriously straight and a stunning shade of red that highlighted my green eye contacts spectacularly. All the work I had put in was about to pay off with the man of my dreams.
For the first time ever, my desires had been admitted out loud and into the universe. Todd altered his grabbing and rubbing into a slow and sensual caress. His hands flowed along my body and slid along my thighs, teasingly brushing by my cock. It was both wonderful and insanely frustrating. I was nearly ready to blow my load right there, but I think Todd sensed it and wanted to tease me. As his lips pressed up against the curve of my long neck he turned me around and as I had requested, gently eased me down to my knees.
Without another word, he unzipped his pants and withdrew his cock from its hold. Now free, I could see it pulse and jump as he brought it forward to my lips. I didn’t hesitate to open my mouth and suck the head. He put his hands on the sides of my head and started slowly drawing his throbbing cock in and out of my mouth, trying to push it further each time he stroked forward. I couldn’t take him very deeply, but I sucked for all I was worth. As I sucked his cock, I swirled my tongue around his shaft and rubbed his balls.
If I’m telling the truth, even though this was what I had asked for, I was afraid. Afraid to give in to my desires. Afraid that there was no going back once I completed our tryst. Afraid that I would never want to walk as a man in the world again.
All these thoughts and more swirled through my head as I continued to lick and suck his dick, but before I could change my mind and stop, Todd grabbed my head firmly and began to pump stream after stream of cum in my mouth. Being a guy myself, I understood what was going to happen the moment his grip became so unmoving and insistent so I was ready. I tried to hold it all in, but there was so much that a little spilled from my lips, dripping out the side and onto the front of my blouse. With his cum expelled, Todd’s cock began to shrink and at that moment, I stood up and kissed him on the mouth like I should have done all those years earlier.
It was everything I imagined and more. When our tongues met it was a dance for the ages rather than a duel to the death. Todd’s cum flowed back and forth between our mouths as our tongues tried to intertwine themselves into one being. As his cum danced along my tongue, I finally couldn’t take it anymore and swallowed all of it greedily. As our lips slowly parted, I kissed and licked the small amounts that had been expelled from our mouths and had eased their way onto Todd’s lips and chin. It was a moment of magic I will never forget and to this very day is the most sensual kiss I’ve ever experienced.
Still flying high from the passion of our kiss, I didn’t resist when Todd turned me around and put me back on my knees, this time, facing away from him. He gently, but firmly pushed my chest to the floor. Todd then lifted my skirt and pulled my panties down around my knees. As I lifted my knees to let him pull them further down, he surprised me by biting an ass cheek. The rush of blood that went to my face shocked me as I went beet red. I’d already blown him, shared his cum in my mouth, was down of the floor with my panties around my ankles and a bite on the ass managed to make me blush?
Before I could dwell on that though, Todd spread my cheeks apart and buried his tongue inside my ass with one thrust.
I kept my head resting on the floor and my eyes closed as I heard him start to walk away. I thought my heart was going to break as doubt and embarrassment flooded through me. How could I have been such a fool to think a man as hot as Todd would want to be with me instead of a real woman? I couldn’t help but begin to cry softly as my thoughts dropped me into a pit of instant depression. There I was, the fool, with a man’s cum on my lips, panties around my ankles, and my bare ass up in the air.
After a few minutes, I heard footsteps coming back and Todd dropped down to my side. I could feel his breath on my face as he gently rubbed my cheek and gently asked, “Why are you crying, Katie?”
With his assuring presence steadily beside me, I finally opened my eyes a few minutes later to look at him. He was lying on the floor beside me, looking at me with that lopsided grin of his I had loved so much when we were younger. “I was afraid you had changed your mind and left. That you had decided this was a mistake and would never want to be with anyone that wasn’t a real woman. That you had abandoned me now that you’d gotten your rocks off.”
I don’t know what I was expecting after that, but instead of being angry or upset, he just chuckled lightly and shook his head. He leaned forward and kissed me tenderly for a while before holding up a bottle of lube in his hand and saying, “Of course not, silly. I just went to the bathroom to get some lube. I know you said you wanted me to just take you, but I thought this would be better and ensure we have a special night.” Kissing me with a little more tongue this time he added, “You always were a bit of a goof, haha.” I smiled at the memories of our youth and planted my tongue firmly into his mouth in a passionate embrace.
Laughing lightly and being even more relaxed than I had been earlier, I kissed him on the cheek and said, “You’re right. I’m a goof and even a bit of a drama queen sometimes. But what I want to be right now is your little sissy slut so stop laughing and get your cock in my ass now mister!” I stuck my tongue out at him as he got up and said, “Okay, okay. Your wish is my command, Katie.”
With that said, the laughter was over and my night of imagined hot sex was finally becoming a reality. I had used toys on myself for years, but I had always desperately wanted to feel the warm and hard flesh of a man making his way into my ass. I can’t count how many times I had dreamed of this very moment and the excitement of it becoming a reality made me forget about my previous tears and fears instantly. The only thing my previous emotional sharing with Todd had done was make me hotter for him than I had ever been before in my life.
Todd stood behind me and lowered himself so his cockhead was resting against my puckered asshole. I wanted to feel it inside me so badly that I squirmed and pushed back, trying to slip him inside me, but he kept pulling back, just enough to keep his hard cock pressed against my hole, but not entering. “Say it,” he said. “Say you want me to fuck you and we’ll complete your fantasy.”
I leaned a little further forward, pushed my ass further into the air, and tossed my hair as I turned and looked him dead in the eye and in a clear voice said, “I want you to fuck me. I want to feel that hard cock of yours buried in my ass. I want you to fuck me until I can’t take it anymore and beg for your cum deep inside my asshole, Todd, so fuck me. NOW!”
I think my sudden forwardness took Todd a little by surprise as he stood there, stunned, still pressed against me. “Well?” I asked. With that, Todd squirted some lube on his cock and began stroking it. With a wicked glint in his eye, he gave me a grin and asked, “Is this what you want? Is this the cock you want?”
I nearly screamed, “YES!” at him.
Rather than reply back, he finally lowered himself further, and we were off.
He pressed the head of his cock against my asshole and rather than tease me like before, continued pressing down until he started to make some progress. He’d then pull out and lower himself again, going deeper each time. Each stroke felt more wonderful than I had ever imagined it would, but at this point, I was a raging storm of hormones and desperate for a real fucking, so I looked over my shoulder and winked at him before saying, “Come on, big boy. Bury that hard dick in my ass. Bury it to your balls and fuck me like you mean it.”
I thought I might shock him again, but the moment the last word was out of my mouth, he shocked me instead and did exactly what I asked. Like a rock plummeting from the side of a cliff, he just dropped his weight on me and in one exquisitely wonderful stroke, planted his cock balls-deep in my ass. The suddenness of it took my breath away, but I had asked for it and Todd obviously planned on giving me exactly what I had asked for as he never gave me a chance to catch my breath and just started fucking me for all he was worth.
For more years than I can even remember, I had dreamed of being fucked by a real cock, but even in my fantasy I had never imagined it would feel so good. Todd’s cock wasn’t too thick and was a little over seven inches long – the perfect size to fuck me into delirium and that’s just what he did. I was so absorbed with feelings of ecstasy cascading through my body that I continually seemed to leak a solid stream of pre-cum on the floor.
I honestly couldn’t tell you if Todd fucked me for an hour or if it was only for a few minutes. I just know I lay there in amazement as I felt his cock plow my ass with abandon until he suddenly stopped, pulled almost all the way out, and then shoved himself completely into me in one fell stroke again, pumping what felt like buckets of cum deep in my ass.
As I had said before, I had used toys for years, but nothing could prepare me for the feeling of Todd’s cock swelling up and pumping his hot cum into my intestines. The intense sensation of his load coating my insides was the final piece to my life’s puzzle of discovering myself and my sexuality. With that load of cum, everything came to a head and my body could hold back no longer.
The years of desire, the hotness of giving him a blowjob, my emotional breakdown when I thought he had left, and his loving tenderness when I discovered he hadn’t. All of it came to a boil and for the first time in my life, my cock let forth a load of cum with no touching from myself or someone else. I couldn’t believe it as stream after stream shot forth and covered the floor and later, my skirt and blouse as Todd collapse on top of me. He turned me over and kissed me lovingly for what seemed like an eternity before we were both ready for round two.
That night was just the beginning of what I would soon discover was my new life.
