Becoming a Sissy Slut Pt. 01

I can say that I've lived a rather ordinary life. Having been married for 22 years, raising a few children, and even retiring from a job after 20 years, my life has been rather full, but ordinary. This wasn't always the case and looking back I sometimes wonder what my life would have been like if I had been able to follow a different path, one that I lived for almost five years of my life and one that I will never forget. I guess I should start at the beginning.

When I was much younger, as a teenager, I went through a very tragic moment in my life. My cousin, who was like an older brother to me, passed away and left me in a very dark place in my mind. Seeing as how he was pretty much the only member of my family who I talked to or that paid any attention to me, his loss left a gaping hole in me that I never thought would be filled.

That was until a few weeks after the funeral a family friend, Henry, stopped by my house. Being as he was much older then me, around 25, I figured he was there to see my father, who lived with, but was either working late or romancing whatever girlfriend he currently had. When I told him this he shocked me when he said he was there to see me and wanted to see if I wanted to hang out with him. I was in such amazement that I had no idea what to do, but we started hanging out, going to different places, and even just chilling over at his house. Since it was summer I was able to spend more and more time with him, eventually being able to spend the night or the weekend with him. Every time we hung out I would look at him and see his smile, a smile that warmed me to the core, and a smile that would lead to more things. After about a month of spending time with him is when things took a serious twist.

We were hanging out at his house and since it was a hot summer day we were out back and decided to have a water fight. I got him a few times but he had decidedly won since I was soaked from head to toe. We were heading in when a blast from the A/C send a shiver through my body. He told me to go ahead and get a hot shower before I got sick so I made my way to the bathroom trying not to drip water everywhere. When I got there I stripped down and got in, enjoying the hot water compared to the cold wet clothes I had dropped in a pile on the floor. When I went to use the soap and shampoo I was a little confused because all I saw were feminine type products. Shrugging it off I used the soap and shampoo and enjoyed the flowery fragrance they left on me. When I finished I stepped out and dried myself off with the fluffy towel left for me. Looking around I finally noticed that the pile of clothes I had left on the floor were no longer where I had left them. I made my way down the hall to the living room where I saw Henry sitting on the couch, shirtless, watching something on the TV that he quickly paused as soon as he noticed me in the hallway. I asked where my clothes were and he told me they were being dried but he might have something for me to wear in his bedroom.

I followed him and sat on the bed, wrapped in the towel, the cold air starting to put goosebumps on my skin, while he searched through his closet. Finally he produced a large bag and smiled as he showed it to me and then proceeded to dump the contents onto the bed. I was shocked and really confused with what I saw. He told me all he had was his little sisters old Halloween costume that would fit me and what was on the bed started to make sense. There was a pair of black lace panties and matching bra, a plaid mini skirt, a white tie blouse, a pair of thigh high white stockings, and a pair of shiny black flats. I looked at the items and pondered whether to wait for my clothes or just suck it up. Another shiver running up my spine from the cold A/C made the choice rather easier. I bit my lip as I decided to just put the clothes on as opposed to sitting around in the cold in just a towel.

I slipped on the panties first, letting them slide up my legs before standing up to pull them up into place, covering my little cock in the smooth fabric. I could tell by the stirrings I started to feel that I was beginning to enjoy wearing them. Then I slipped on the skirt, the stockings, and the shoes, each piece of clothing becoming easier and easier to slip on as my resistance shrunk more and more. Henry helped put the bra on and finally I slipped on the blouse, tying it in the front. Henry stood back and smiled at me with that same smile that would melt me every time as I showed off for him. He told me there was something missing and dug back into his closet, quickly producing a box that he laid on the bed. I opened the box and inside were a red haired wig and a couple of strange looking mounds. He told me they would complete the outfit, so I let him help me with the wig and even sticking the, what I found out were breast forms, to my chest under the bra. He stood back again and whistled, turning me to look at myself in the mirror. I didn't even recognize the person looking at me.

He took my hand and led me back down the hall to the living room, sitting down first and then pulling me down practically on top of him. As I landed next to him I had to brace myself, one hand landing on his chest and the other landing on his groin. I looked up at him shocked and apologetic but before I could remove my hand from his crotch he placed his on top of mine and just simply smiled at me. I was still a little confused but relaxed more when I saw that smile, although I could feel his cock growing under my palm. He nodded towards the TV and resumed the movie that he was watching before. I didn't know what to think but on the TV screen was a woman with red hair and a man in nothing but shorts sitting on a couch.

The woman started rubbing the mans crotch through his shorts and at the same time I could feel Henry moving my hand to follow the same course. He told me to just pay attention to the movie and I watched the woman move faster and faster, so I started moving my hand faster to match. Then the woman pulled down the mans shorts pulling his cock out of his pants and grasping around it, stroking it up and down. I looked at Henry, smiling at me, and decided to follow along, pulling his cock out of his pants as well, stroking it in time with the woman on the TV. Suddenly the woman bent her head down, taking the cock into her mouth with ease, bobbing up and down on it again and again. I was confused but felt Henry's hand on the back of my head pushing me down towards his growing cock.

I can't say I put up much, if any, resistance as I wanted to please Henry for showering me with such affection before. As my face got closer and closer I opened my mouth feeling the head of his cock pass my lips, the taste of his precum smeared on my tongue. I tried to take as much as I could but gagged time after time only able to get maybe half of it in my mouth. He reassured me and told me we would work on it. Watching the woman bobbing up and down I tried my best to match her speed. Then the man pulled her up and had her crawl on all fours in front of him. I pulled my mouth off of Henry's cock and looked up at him, seeing him smile and gesture to the floor.

With little thought I crawled onto the floor on all fours in front of Henry, feeling my own excitement in my cock as it leaked wetting the panties I was wearing. I felt his hands behind me, sliding the skirt up, pulling the panties down slightly exposing my ass but leaving my cock encased in the black fabric. Then I felt a cold gel pushed inside me by his finger, slowly pushing deeper and deeper. I groaned and moaned as I felt my ass opening and stretching to accommodate his finger. I felt him pull his finger out, my asshole seriously lubed, but leaving me with an almost empty feeling. I could feel Henry shifting behind me and my eyes went wide when I felt the head of his huge hard cock pushing against my hole. I cried out as he tried to push it in slowly, tears forming in my eyes. He placed something under my nose and told my to breathe in hard. I sniffed up as he squeezed the bottle as he pushed it into my nostril. My mind exploded in vibrant colors and any pain I felt seemed to slip away, replaced by a building lust and need. I felt him pushing his cock inside me again, this time there was no pain but rather a growing need to feel his hard throbbing cock inside me.

Inch by inch he pushed it inside me, my ass stretching more and more. Moaning and groaning feeling more and more full I finally felt his hips against mine as he buried all of his cock inside me. Pulling back and pushing in again and again, faster and faster, deeper and deeper. His groans and moans made my body quiver with lust, my own little cock slapping me in the stomach leaving a thin trail. Louder and louder I moaned, starting to push back against his thrusts. Grabbing my hips I felt him thrust one last time, his cock growing inside me as he started to shoot his hot cum deep inside my bowels.

I moaned like a whore as I felt his seed filling me up, my own cock spewing cum into the wet panties that encased it. He held me there as he shot load after load inside me, finally releasing his grasp as he finished. Still dazed I barely noticed his cock slide out of me, or the plug he shoved into my abused hole, keeping his hot cum in my belly. I was lost in list as I felt his hand on my head, turning it as he pushed his cock into my mouth. My taste buds exploded with the tastes of lube, his cum, and my ass, and as he pushed his cock in and out of my mouth I graciously sucked on it, cleaning it thoroughly. I felt his hands around me as he picked me up off of the floor and carried me to the couch, putting me cuddled up to him.

As I laid there trying to collect my thoughts and coming down from the lustfully high I was on, I looked up at Henry's face and saw him looking at me with that great, warming smile. I smiled as well, feeling his arm encircle around me, the heat from his chest, his cum still swishing around inside me. I sighed as I snuggled into him, knowing that from that day forward I was HIS to do with as he pleased.