Cockwhore's Special Evening
Keywords: Evening, Special, Cockwhore's,
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It was Friday night and my wife had just left on a weekend business trip. I helped her pack all of her bags, she always packs too many suitcases, and waved goodbye from our front door as she drove away. I love when she takes these frequent trips because it provides me plenty of time to indulge my darkest passions and desires, desires that can only be fulfilled alone in the privacy of my own home. This night would be special however, because the day before I had gone to the local adult video store and made some expensive purchases that would ensure an explosive and heart-pounding night of ecstasy. As I raced downstairs to our finished basement my cock started to swell in anticipation of the night that lay ahead.
As I unlocked the trunk that held all of my "secret" items, both new and old, the first drop of precum started to soak my white, tight underwear. I shoved my hand down the front of my briefs and caressed the tip of my cock with my index finger, drawing out the oily, salty liquid. My heart was pounding as I brought my hand to my mouth and licked the hot juice off of my finger. Then I opened the bag containing my new purchases and spread them out over the couch making sure everything was there. Thoughts of my time spent shopping for the new toys awakened more lust and my cock swelled in response. Trips to the video store always get my heart pounding, and the smell of cum flying from the dicks of horny men watching movies in small booths had overwhelmed me as I strolled the aisles searching for the perfect additions to my cross-dressing fun.
Looking at the new items made me realize that I was lucky I had made it out of the store and back home without passing out from excitement. I opened the plastic box from a new 10" rubber cock that had a suction cup on the bottom and caressed it as I dreamed of the pounding that this thick, manly cock would be giving to my ass later that night. My other purchases would add to my feminine collection and complete my transformation from a 23 year-old, average man into a hot and horny young slut that could milk the semen from a room full of hard cocks.
I spread out my new 4-inch platform red pumps, black stockings with frilly tops, long black half-gloves, and a tiny little g-string one size too small for my tight body. I also pulled out a black training-bra I had bought at the mall and looked over the new gangbang movie I ordered online. This film promised to make my penis into stiff wood and guaranteed a good cock milking. Heading into the basement's bathroom, I took the huge, fake cock in with me to test the suction cup and see if it would actually stick to the shower wall. I had dreamed for years of buying a dildo, but my conservative wife would hear nothing of it as she assumed I would use it on her. If she only knew of my fantasies and the games I played during her absences! I gripped the giant, fake dick in my free hand as I reached into the shower and turned on the water. The feel of this horny toy caused the blood to rush out of my head and my penis leaked more juice. I was so turned on that I had to fight the instinct to just drop down on my knees and shove that lovely rod into my ass right then and there. I like to be freshly clean for my nights of play and I wanted to make this special weekend last.
As the warm water of the shower hit me and I began to shave my legs, arms, ass, and penis, thoughts of hot man-cock swirling in my brain. I don't consider myself gay, bi, or straight, labels have little meaning to me, but I prefer for my secret life to remain private and I live the life of a heterosexual guy in public. I love the site of a tight, shaved pussy, but at the same time, giant porno cocks have always turned me on. Seeing porno sluts taking thick fuck-poles the size of a woman's arm is enough to send me into fits of orgasms that leave me breathless, wet with cum, and grasping my aching boy-cock. I long for both a woman's ass clamped around my hot pole and dream of meaty fucksticks in between my lips as they fill my young mouth full of cum.
When I dress up as Cockwhore, a name I gave myself years ago when I first put on a pair of my sister's tight panties and jacked-off into the front of the cottony, pink material, I first make sure my little fuck-hole is clean. Usually I have to use my fingers to stretch out my little ass in order to clean myself, but tonight I would use my new fake cock to do the job. After I finished shaving I got down on my knees in the shower and arched my back so my ass would be ready for cleaning. I'm the perfect size to dress as a girl and have no problems reaching around to caress the entrance of my fuckpipe. I lathered my pink, tight anus with soap and the slight burning that the cleanser leaves behind never fails to stimulate my cock. With my left hand now holding me up for support I grabbed the big, fake dick and rubbed it around the entrance of my fuck-hole, my hand unable to fully fit around the dildo. The shower is large enough to allow me to spread my legs fairly wide and my body began to shudder with anticipation and the nervousness of trying something new as I slowly, very slowly, began to ease the huge thing into my hot ass.
I couldn't believe how it felt as the head started to penetrate me. It was a mixture of excitement, pleasure, and pain. I've only been able to insert two fingers in my ass before, but this monster was thick. Watching pornos I had always dreamed of taking Peter North into my willing hole then eating all of his cum, but this dildo was even bigger than his cock. The thing was stretching my anus to its fullest and my legs started to give out from underneath me. I couldn't hold myself up with one hand any longer because I was shaking so hard from the excitement. Removing the cockhead from the entrance to my ass I reached back to the shower wall and used the suction cup to keep the monster dick attached and pushed it into place. It held the armed-size cock as it was supposed to, but the thing was so big that it flexed downward. This really turned me on because it looked so natural at that angle and I quickly backed up to rub my ass on the rubber head.
With my cock growing harder every second I got the monster toy into my ass about half an inch and then backed off. I did not want to "pop my cherry" yet and I sure as hell did not want to come so soon even though my balls were aching for release. With shaking, quivering legs I managed to stand up and rinse all of the soap from my body, being careful to rub the soap out of my tiny little ass-pussy with my fingers. I rinsed and washed my new toy, dried myself off, and headed out into the basement den to begin the transformation into Cockwhore.
Rooting into my trunk of onanistic pleasures, I looked for my special skirt and top. Last year I got really serious about my cross-dressing fetish and bought a plaid skirt with a white blouse. I don't know what it is about this outfit, but wearing it sends my balls into a boil and the orgasms I have while dressed up like a naughty schoolgirl are tremendous. I also pulled out my cheap make-up kit and blond wig. I had to remove all of my movies and magazines from the trunk to find my wig but I just left them strewn out on the soft carpet. It was going to be a long weekend of jacking my cock and I had plenty of time to clean up my things before my wife got home.
The first thing I do when dressing up as Cockwhore is to put on my wig. This was going to be a special night and I decided to use some pink ribbons to tie my hair off into long ponytails that flowed down to my shoulders on both sides. Checking into the full-length mirror to see if my wig was on straight I adjusted the frame at a slight angle. The mirror allows me to watch myself masturbating and is highly adjustable, allowing me to see all of the naughty things that Cockwhore does to herself. Next I applied the cheap make-up using bright blue eye shadow, hot-pink lipstick, and dark mascara. I'm not very good at putting on make-up so I always end up looking like a cheap hooker when I'm done, but this makes me even hornier. When I put on the heavy lipstick I made sure to spread it thickly and I made my mouth into a small circle to see the effect. I looked perfectly trashy and my aching balls started to let me know they needed some release, but they would have to wait. I can spend hours stroking, fondling, and jacking my cock. The longer I can hold out by edging like this, the larger my orgasms are and the more hot cum I will shoot.
Next came the half-gloves and training bra. I like these gloves because they have little loops at the end that I slip my middle finger through to hold them in place. They extend all the way up past my elbow and the training bra was a perfect match to the gloves. I opened a package containing my new stockings and rolled them up to my thighs. The elastic that held them up was covered around with a soft, fluffy frill that got me steaming. There is nothing like a pair of stockings worn by a fuck-hungry slut to make me cream in my hand. Wearing them now really got me going and my boy-cock took notice as my hardon grew and grew. When I slipped the tiny g-string over my hips and into the crack of my freshly-shaved, virgin ass I had to sit down to try and relax. With my heart pounding in my chest I put on my white blouse and tied the bottom ends below the training-bra and above my tight belly. I pulled on the red plaid skirt and zipped up the back zipper. I pulled my black g-string above the tops of my skirt so I could see the black straps high on my hips.
The only addition to my outfit left was to try and put on the red platform fuck-me shoes. They were definitely hot, but I had never worn a pair of women's shoes before. I slipped my little feet into them and could feel my cock straining the silky material of my slut panties. After buckling the tops of the platforms I stood up and quickly realized how hard it was to walk around in them. It's such a turn-on to see a hot slut fucking in platform pumps and I wanted to get the hang of being able to walk in them.
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Keywords: Evening, Special, Cockwhore's,