A journey to becoming a sissy slut

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 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 and 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 throughly. 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.
After that first night Henry would always have me dressing up whenever I came over, even having his sister come over and give me lessons on how to do my makeup properly to give me several looks from innocent girl to trashy whore. I was a quick learner and very enthusiastic to be able to make Henry happy. In addition to the makeup and the outfits he started having me wear higher and higher heels, working up to three inches in just under a month, as well as increasing the size of my adhesive breast forms moving from B to C to D. He would also give me a good enema or two when I first got there and then would inject a heavy amount of lube, sealed off by a plug to keep it in.

We made love every day, several times a day, trying different positions in different rooms such as riding him reverse cowgirl on the couch in the living room, doggy style on the kitchen floor, and even missionary in his bed to give just a few examples. I got better and better at taking his cock into my mouth, even being able to get over my gag reflex and take his cock down my throat. I loved to feel his cum inside me whether in my ass, which he had me refer to as my pussy and which he would plug after ever time keeping his cum inside me, or my mouth, that I would show him the generous amount of cum that filled it before I would swallow it down. I did anything and everything I could to make him happy and the more I saw that smile on his face the more I became his.

After I had gotten comfortable walking around in my three inch heels and my enlarged chest Henry decided that we needed to go to the store for a few things. Having never been outside of the house dressed up I was worried that people would recognize me. He reassured me, having me stand in front of the mirror to see myself, and I have to say I would never have recognize me even if I tried. Henry pointed out that there was only one issue, pointing down to my slowly growing erection in my satin panties. I grew a little embarrassed but he told me he had a way of fixing that problem producing a small plastic device. I looked at his curiously as he slid my panties down and felt him afix the device to my cock making me groan in discomfort as my cock strained against it, hearing the click as it locked in place. He told me now it looked like a clitty and that I should refer to it as that from then on. He pulled my panties back up and I fixed my skirt, noticing that the bulge that had begun growing wasn’t an issue anymore. The discomfort grew more and more as my clitty strained against the chastity device but he assured me that I would become used to it. Then he told me he had something for me that might help me take my mind off of it and felt him slide the strip of my g-string to the side, feeling his hands rubbing up and down my pussy crack. Suddenly I felt a slight pressure as he started pushing the plug up into my well lubed hole. He bent me forward giving him better access and with one steady push, a moan escaping my lips, he shoved the large plug into my rectum, my pussy stretching to accommodate the large intruder but closing around the base locking it in place. Standing me back up the sensations from the plug spreading pleasure over my body mixed with the pain of my clitty straining against the cage. My mind was a blur of emotions and I was putty in his hands. He smiled at me again and again any resistance I had melted away.

He took me by the hand and led me to the front door, going slowly so I could get used to the constant throbbing of my confined clitty. Thankfully by the time we got to the door I was getting more and more used to it and able to compose myself. I resumed swaying my hips on the way out the door and to his car, opening my door and ushering me in. We drove the 30 minutes and stopped in front of the local mall. My nerves were starting to act up again as we stopped and parked, Henry getting out and coming around to open my door. Just seeing his smile and taking his hand calmed me down and made me feel so safe that I wasn’t bothered by anything. I got out of the car and swayed my hips as we made our way to the mall, his hand on the lower part of my back to guide and reassure me. My nerves started in again as we got closer and closer to a group of boys out in front of the mall but as we passed them I heard their cat calls after me and it made me grin from ear to ear, my nerves settling once and for all.

We walked up and down the mall, finally stopping in front of a Victoria’s Secret. We walked in together and started browsing through the different lingerie sets, Henry picking out several he wanted me to try on. I made my way to the changing room and began to undress, looking in the mirror and admiring myself. Suddenly I felt something stirring inside me, more specifically in my pussy. A small vibration started buzzing from my pussy and sending wave after wave of lust and need over me. More and more it started to pick up speed and I heard myself even beginning to moan again and again, but as the sensation filled me with desire my attention fell to my encased clitty. Pain and pleasure wracked my body as the vibrations from the plug increased again and again causing my clitty to attempt to harden but failing to do so because of the cage but instead making it leak again and again soaking the crotch of my lace panties. My legs shook as the sensations became more and more powerful, my head swimming, and my vision blurring. I heard a knock and the sweet sound of my Henry’s voice asking me if I was ok. I opened the door and he hurried in closing it behind him. The lust in my eyes must have been apparent because I saw him curl his lips into a smile and undo the button on his pants. My body moved as if by reaction, dropping to my knees and unzipping his pants, pulling them down with his boxers to expose his growing cock. I took it voraciously into my mouth, so lost in lust I took it all in one gulp not even caring about any gagging I may incur. My throat made no resistance as his cock slid into it over and over, his cum heavy balls smacking my chin as he thrust repeatedly. Spit began to collect on my lips, dripping down my chin as his cock slid in and out of my mouth. I could feel it stiffening and throbbing as he pulled it out of my mouth and had me stand up, turning me around and pushing me up against the wall. He pulled the back of my panties down and grasped the vibrating plug, pulling it with one solid movement. I moaned as I felt the emptiness in my pussy that the plug had left in me.

I didn’t have to wait long as I felt Henry’s hard cock push at my opening, sliding in with ease from all the time we had been having sex again and again. With one thrust I felt him bury his cock all the way inside me, his hips smashing against mine. I moaned louder as I felt him filling me up, his cock throbbing and pulsing inside my pussy. I felt a soft fabric push into my mouth and realized Henry was pushing my other panties, soaked with my clitty juices as well, into my mouth to stifle my moans so as not to alert the other people in the store. He rocked back and forth, his cock easily siding in and out of my used pussy building up tempo faster and faster. I moaned again and again into the makeshift panty gag, the lustful sensations raging through my body, making me push back with every thrust, getting him as deep inside me as I could. Over and over I felt him thrusting inside me, his hands moving up my body to my large breasts encased in the lace bra. After a bit I felt his cock growing again and then the wonderful rush of his cum spewing into my bowels, load after wonderful load. The hot sensation pushed me over the edge and I felt my clitty pulse in its cage leaking heavy blobs of cum into the crotch of the panties. My head was spinning coming down from the sexual high and I felt him slide out of me, quickly replacing the plug to catch the thick cum inside my pussy. He removed the panties from my mouth and helped me to fix myself, the hot cum still churning and swishing around in me. I was still in a dazed state as he got me dressed and led me out of the store after paying for the lingerie I was currently wearing as well as several others. I’m not sure if the cashier knew what had happened but from the sly look on her face I’m sure she did. We made it back to the car and drove home, his cum still swishing around in my insides, my clitty still in an almost constant state of leaking.

By :

Check Also

Discovering a wet fetish

It was summer. And time for our annual extended family camping trip. We’d done it …

Leave a Reply

Your email address will not be published.