Cockwhore's Special Evening

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. As I struggled to maintain my balance it became apparent that the easiest way to walk around was to relax my back and let my tight ass stick out. I had never felt so sexy before, my cock responding to my transformation by straining the g-string even further and I pulled the thin straps high above my waist. After a few minutes of strutting around like a street-whore and imagining myself up for sale to hundreds of horny men, I got used to wearing the shoes and I put my new gangbang DVD into the player and turned on my large-screen TV. Going back to the couch I adjusted the mirror so it was pointing downward facing me and for the first time I stared at myself dressed in my new clothes. I was most definitely Cockwhore now. Staring back at me in the mirror was no longer an average, married guy, but the most trashy looking slut I could have imagined. I looked hot enough to milk the cum out of a train of the most hardened porno studs and my cock responded. It strained outward against my g-string and I could see the bulge pushing out the front of my pleated skirt.

As the credits to the gangbang movie started I began to dry-rub my cock on the outside of my naughty skirt. I brought one hand to my training-bra and began to rub my tiny chest. I looked so horny, so hot, so fuckable in this outfit, but I had to maintain some semblance of control in order to enjoy my special time alone to its fullest. I swayed my hips around as the movie began, turning around to look back at my hot ass in the mirror. The stockings were a turn-on and I bent over maintaining my balance the best I could while I hiked up my schoolgirl outfit just above the bottom of my tight, virgin butt. I could see the crotch of the tiny g-string riding my ass and I rubbed the rim of my boy-pussy with my finger. My cock responded by leaking hot precum into the material of my slut panties and I knew it was time to sit down and check out the movie before I was left gasping after a premature orgasm.

This film had a few scenes of gangbangs and I hoped it would be a good one when I ordered it. I was not disappointed at the first scene as I gazed into the TV and saw a fuck-whore on her knees sucking cock. There were ten guys surrounding this big-titted slut. She must have been about thirty and I couldn't help thinking how much cock she had taken during her lifetime. She was obviously a pro and was stroking these men to full erections. The size of their pricks was outrageous. I never get penis envy when watching a porno. Instead, I have always fantasized what it would be like to have my mouth treated like a pussy by a room full of hard men. She was expertly gripping their meaty shafts with one hand and their balls in the other as she pumped her head rhythmically against their hot crotches. My desire to take her place overwhelmed me and I hiked up the front of my skirt in order to free my pulsing cock from the confines of the g-string.

My head starting to spin in ecstasy as I sat on the couch and began to furiously jack my boy-cock. Their I was, dressed as Cockwhore watching a slut be manhandled by a room full of expert pornstars. She was taking turns servicing their gigantic pricks and drolling all over herself at the same time as they pummeled her throat. Time seemed to suspend itself as I would alternate between looking at myself in the mirror and watching this whore being fucked silly. If I spread my legs wide enough I could push up against the floor with the platforms and pump my cock at a rapid pace. As I gazed into the mirror, the sight of my ponytails and outfit freed my deepest fantasies. I imagined myself in my own gangbang movie, servicing cock after cock. I have never fondled another man before, but I could almost taste the skin of their sweaty cocks in my mouth. As I increased the speed of my jacking the precum began to really flow. It seemed that torrents of the cock-nectar was coating my fingers and the tiny straps from my half-gloves as I alternated hands to give my pole its treatment. Rubbing my balls, feeling myself up, stroking the tops of my stocking-clad legs, and pounding myself into oblivion caused me to begin panting like a bitch in heat. When I get this horny I like to whisper naughty things to myself.

"I like cock," I breathed, "I'm a naughty girl who wants to be fondled by big men."

"You like my outfit?..I wore it to turn on your cock...Do you like to fuck girls in the mouth?..I suck cock and eat cum" I whispered under my breath, "Feed me your hot cum...I need to taste it...I need to be pumped full of sperm like the whore I am."

As the woman in the gangbang movie was being double-penetrated by two hung studs, a third and fourth man sprayed her face with hot juice. It was my first vision of the milky substance this evening and I got even more turned on. All I wanted was to eat the cum from a hundred cocks. I wanted to drink it. I wanted to be gagged by large fuck-poles. My top lip began to sweat and my pulsating cock was itching for release as I imagined tipping a glass full of cum to my lips and gulping the man-juice down my slut throat. I was in ecstasy as I pumped my cock and talked like a little whore. The words spoken to release my passions and desires.

"Cockwhore wants cum...Cockwhore needs to feel your big meat in her little hand...Do you like my pussy?.. I want cum on my face," I moaned, "I'm a naughty little slut who wants to be pounded by her big fuckdaddy."

On the screen, all of the men were now pumping long streams of jism onto the face of the the slut. Long ropes of sperm shot out from their rigid poles onto her face and huge tits. She was covered in their sweet juice and I was approaching orgasm. Edging takes practice and I was afraid of releasing my aching balls too soon so I decided to take a break. Reluctantly I released the iron grip on my boy-cock. It was screaming for release, but I wanted to enjoy my transformation and would only fully spray when I couldn't take it anymore. I paused the video and stood up on shaky legs, saving my full release for later. Walking up the carpeted stairs was difficult, but I felt too horny in my little outfit to take it off. The front of my g-string was soaked with precum and my hard-on pulled the back string tight into my round ass. I was dizzy with desire as I grabbed a glass of water from the kitchen, the liquid would make sure I stayed hydrated and would also help to increase the volume of my cum when I finally had an orgasm.

I grabbed my smokes and went outside into the cool night air of our screened-in back porch. I took a seat on quivering legs in a lawn chair and sat enjoying my cigarette. It was nine o'clock and I had been stroking myself for about a half-hour. I can go for 2 or 3 hours straight some nights by edging myself close to orgasm then releasing my grip from my cock before I spurt the salty cum. Edging is one of the most enjoyable feelings in the world, and dressed like this I wanted the evening to last.

I was startled by the sound of a car pulling up next door and was glad the lights of the porch were off. I recognized the sound of my neighbor kid's muscle car. Todd is a nineteen year-old enrolled at the local community college and still living at home. We've hung out together because I'm only four years older then him and I would hate for him to see me in this condition, the embarrassment would be too much. His dad is cool, and my wife and I invite the whole family over sometimes for barbecues. I heard Todd go inside and I made my way back downstairs to continue my evening of pleasure.

I restarted the movie and decided it was time to experiment with the huge dildo. I dug in my trunk for some lube and brought the small container over to the couch. I grabbed the giant dick and sat down, getting turned on but a bit anxious. I wasn't sure if I was going to be able to handle this thing without shooting my load prematurely. I sat back as the next gangbang scene began, this time with what looked like a streetwalker being fucked silly by a group of men outdoors. The scene took place in a well-lit alley and was different from the opening one because the fucking was more intense. They just started plowing into this fuckwhore, dry fucking her ass and abusing her mouth. She was taking cock after cock in all of her holes with little preamble. They were tossing this tiny little hooker around like a ragdoll and I was getting turned on as I imagined myself in her place.

I gripped my boy-cock in one hand and with the other I started stroking the giant dildo next to me. I placed it on the couch pointing straight up to simulate someone sitting beside me. My mind began to drift off into wild sex fantasies. I was a whore prowling the streets for men. I was a cock-milking slut who used her mouth to drain men of their seed for money. I opened my holes for any takers. I spread my legs further and further apart as my lips, covered in the cheap, pink lipstick, were open in pleasure as I imagined them covered with the cum of my johns. I wanted to be a whore more than anything and I thought of the pleasure that giant, rubber cock sliding in and out of my ass would bring.

I brought the fake cock to my lips and began to suck. I pretended that this was a real cock, a man's cock getting hard in my mouth. I opened as wide as my tiny mouth would go, gorging myself on the imagined man-meat. I was edging so close to orgasm now and the rhythmic pumping of my hand coincided with the pumping that the gangbanged fuck star was receiving. With growing anxiety I stood up and grabbed the bottle of lube. Squeezing a small amount onto the cockhead of my giant dildo I positioned my body upright on my knees on the couch, making sure I could see myself and the action on screen at the same time.

I was ready to try and fuck myself with the giant, rubber rod and I eased the tight material of my g-string over to one side of my hot, virgin ass. Gently I pressed the rubber flesh of my new lover into the tight folds of my boy-pussy and felt the coolness of the lubricant. I positioned myself directly above the rubber pole and with the smallest amount of pressure began to sit back on it. The pain was intense as I held the 10" long cock and it began to penetrate me. My other hand rubbed my penis and I used the dripping precum that my cock was leaking to provide me the sensation of a wet handjob. Slowly I lowered myself onto my rubber lover and imagined I was a hot girl pleasing her fuckdaddy with her sweet, virgin pussy. I spread my legs and released my hold on the pliable rubber dong. I brought my little feet together behind me and gripped the sides of the huge cock with my platforms. The cockhead was now almost fully inserted into my aching boy-pussy when an animal lust took over. I needed that cock inside me. I needed to have my cherry popped by that thick rod and I could wait no longer. I pushed as hard as I could, the pleasure I felt overpowering the pain of my ass being plundered and ripped apart. In a few seconds I had 3 or 4 inches of that monster impaling my ass and I realized that I was a virgin no more. I started to grind up and down upon that giant fuckpole and whispers of my desires were released from my pink lips.