The Birth of a Sissy

"Well I was hoping you would make the right choice and join me." Came a voice from around a corner. As I walked into sight, Brian was standing next to the desk in the room, he was still wearing his slacks but had removed his shirt. He had a chiseled physique and a pleasant tan.

"I... When did you..."

"When you finally made eye contact with me by the elevators I knew I had seen those blue eyes before, this morning I watched you staring at the guy from our Miami branch. I was amazed at how blue your eyes were. Come on how many chances are there that I would meet a 6'2" woman with the same blue eyes in this hotel?"

"So you knew the whole time we were talking in the bar?"

"I thought I did so I made the move and was very happy with what I found!" Again with the wink.

"Well here I thought I was passable.."

"Oh baby you are, we had no idea when I sent you the wine, but when you stood to leave I thought there might be more than meets the eye. That's the whole reason I gave chase. You are a tall, fine drink of water so to speak." With that he began to walk towards me. "I hope you know what you are in for 'Katie' I missed out on going out last night with the guys because of sinuses and the jet lag. I have a nut that has built up for four days and I am not jerking this one out myself." He grabbed me and pulled me in close. We began to kiss very passionately and I began to feel the pressure as his cock grew against my leg. He pulled back and pulled my dress over my head, taking my wig along with it. He took no notice of the wig as he revealed me in the high cut red bodysuit and pantyhose.

"Holy fuck, that is amazing baby!! Get over here." I walked to him and he quickly placed his hands on my shoulders, applied some pressure and I obliged by dropping to my knees. He placed my wig back on my head and unzipped his pants. I was face to face with his fully erect eight inch cock, a pearl of precum glistened from the tip.

"I've never... I've actually never been with another man." I stammered sheepishly. What a time to make that confession right?

"Oh! We'll have you ever been with anyone before?"

"Yeah I've been with several girls before."

"Well then you just have to remember what they did for you and it's time to do it to me."

As he said that he thrust his cock towards my face. I opened my mouth just as the precum hit my lower lip and Brian thrust his cock into my mouth. The warmth and saltiness were surprisingly delightful. The tip of his cock quickly reached my gag reflex and I coughed causing Brian to withdraw slightly. Within a moment he was thrusting back into my virgin mouth. By he third stroke I had begun to create a suction for his cock and on the backward slide I allowed the tip of my tongue to caress the underside of his shaft. He must have liked the feeling because he withdrew his cock to the tip and let out a beautiful moan. I increased my suction and as he pulled the head out it made a popping sound. I instantly felt the void in my mouth and craved to fill it again. I reached out and grasping his shaft I pulled his cock back to my mouth. I ran my tongue around the tip and pulled his cock back into my mouth. I could feel the shake in his legs and worried he was about to fall I grabbed his buttocks and drew him further into my mouth.

"Oh my fucking God, I call bullshit, you have definitely sucked a cock before. Uh this is what Daddy needs, a nice little sissy mouth to fuck. Are you that little sissy mouth to fuck?" As I shook my head yes he reached down and grabbed the back of my head to guide me on my duties. I released his butt and worked on unbuckling his pants. As I slid them down and removed his cock from my mouth to remove his underwear, he resumed thrusting his cock into my mouth. He replaced his hands on my head and not knowing what to do next with my hands I reached up and caressed his recently freed balls. "Oh fuck now you've done it" and with that I felt his balls jerk upward and within a split second his cock spasmed. A hot load of cum erupted into my mouth, filling my cavity full. Instinctively I swallowed in an attempt to clear my airway. Just in time to receive the next salty load as it showered the back of my throat. Five huge loads later and Brian pulled his cock from my mouth.

"Holy shit, that was amazing. I can honestly say I have never had anyone swallow a load for me. You are beautiful." He reached down and pulled me to my feet. He leaned in and kissed me passionately again. I was so pleased that he was pleased with me and allowed him to draw me in for a deep embrace. He began to grind his surprisingly still hard cock against my hose and bodysuit. We walked in our embrace towards the desk, letting him guide us to our destination. He released me from the embrace and broke off our kiss. He faced me towards the desk and found his way behind me. From there he pulled my nylons down and I stepped out of them. He placed the palm of his hand in between my shoulder blades and pushed me forward at the waist. He lowered into a crouch and pulled the thong of the bodysuit from my cheeks.

"Oh baby, daddy is about to make you his little sissy fuck toy. Are you my little sissy fuck toy?"

"Yes daddy, please make me your fuck toy!" This was all so new to me but it felt so right, it felt like at this time and in this place, I was meant to be. He opened up a bottle of complimentary hand lotion and squeezed a dollop on my virgin hole. He rubbed it around with his thumb stopping every so often to place pressure with his thumb. As I stood anticipating him sliding a finger into my awaiting hole he stood upright and squeezed the lotion onto his cock. The next pressure I felt was the tip of his cock against my thighs asshole. My heart leapt as I remembered how much his cock had stretched my mouth only moments before.

"This is going to hurt, but don't clinch and remember I do this out of love for you my little sissy" and with that he applied pressure until his cock head slid into my ass. I tried as hard as I could to remember his words and relaxed the best I could. As his head passed into my ass there was pain but also a release of pleasure. I let out a slight whimper and he continued to guide the remainder of his cock into my ever filling ass. Before I knew it his balls were touching mine and he paused. "Oh that's a good baby girl, daddy is all the way inside of you. Do you like that?"

"Yes daddy I do." No sooner did I answer him then he retracted his cock from my ass. The feeling of emptiness made me want to cry, I had just received my first cock and all I wanted at that moment was for it to stay there forever. I didn't have to wait though because as he reached the backward slide to the tip he thrust his cock back into me and as our balls slapped together again I clinched in an attempt to keep this amazing cock inside of me. "Does my little sissy want to keep daddy's cock forever?!?"

"Daddy please don't take it away from me ever again!"

"Well I'm sorry but daddy makes the rules around here!" He pulled his cock back despite my best effort to keep him inside. This time he slid all the way out of my ass and as I looked back at him in an effort to plead with him, he slammed back into me. I let out a yelp and a moan. He proceeded to work up a rhythm as he grabbed my hips and pulled me repeatedly into his cock, each thrust better then the last. As I began to arch my back he shoved me back down. He reached around me and released my cock from its fabric prison. While holding my cock he thrust back into me. The warmth of his hand on the shaft, the cool air of the room on the tip and the feeling of his amazing cock as it pressed my prostate, I came the hardest I had ever come before. As I spasmed in his hand and covered the floor with cum, my daddy unloaded his own load. The rush of cum as he blew load after load into my ass combined with my own release, I became too weak to stand. I slid to my knees on the floor and his cock fell from my ass. As I tried to catch my breath I could feel cum dripping from my ass onto the heels of my feet, my cock resting in the pool of cum I had deposited on the floor.

"Come on baby, daddy needs to get you all cleaned up." Brian lifted me to my feet and I removed my body suit and wig. We walked to the bathroom and he started a shower. As I stood in the water letting all of the nights activities sink in, Brian slowly soaped me up taking his time to clean my cock and balls. As he soaped himself he turned me to face the shower head and began to soap up my back side. He proceeded to slide his now fully resurrected and soaped up cock into my soapy ass. He fucked me to climax again, reaffirming to me that cock was all I would ever need in my life. After toweling off Brian slid into a pair is silk boxers and I slid back into my bodysuit. Brian crawled into the bed and patted the spot next to him.

"Come here and keep daddy company tonight." I crawled in next to him and he pulled me close in a spoon. He kissed and caressed my neck and back. "I wish I could keep you forever in this moment, but tomorrow it will all be over. Will you remember me? Will you remember daddy?"

"Of course I will. I think this will sound silly but you always remember the first time you fall in love."

"That is sweet, I love you too my little sissy boy" we fell asleep in that embrace and though I don't remember what I dreamt about I would like to think it was about the new life I had chosen. The next morning Brian woke me with a beautiful kiss. He had to wake up early to make some meetings. He had woken me a bit earlier then he had to. I had told him at some point the night before that I had a flight out that day. As I laid there on the bed watching him shuffle around the room I felt a sadness that my time in this magical city was coming to an end. Brian came over to where I laid and leaned in to kiss me, while me made out he had once again freed me from my fabric. He wiped the precum from my cock and wiped it on my hole. While kissing me he used his own precum to lubricate his own cock, then lifted my hips onto his thighs and pushed deeply into me. As we kissed Brian fucked me in the most intimate and loving way I had ever been fucked.

It was the perfect ending to the perfect weekend and the most perfect awakening I could ever hope for.