Wendy-Whore            by: Sean McBride

 

It was late Friday night and I had enjoyed a few beers too many. As usual, I was feeling quite randy, so I decided to browse the internet and seek out a little cyber-action. I live in a small town some three hours outside of Dallas, so my best bet is usually to hook up with somebody for computer sex, but there’s always the hope that I might meet a person in a nearby town and more physical encounter might come about.

I logged on to a favorite web site and ran a search by zip code. There were several men online, but no women nearby. So I expanded my search and licked my lips as the myriad Dallas listings scrolled by. In the big city there were women looking for everything from "just a friend" to a "complete and totally devoted sex slave."

Best of all, these women weren’t afraid to post a picture with their ad.

My eyes were drawn to "MissKriss666," a 36 year-old dom who was looking for a female or sissy male sub to use "as she saw fit." It sounded good to me, and her picture was a wet-dream fantasy come true. She was a tall, raven-haired beauty who was wearing a black corset that left her magnificent breasts on display. She held a leather paddle in her hands, and by her stance, it looked like she was impatient to find somebody to use it on.

It was one of the most exciting pictures that I had ever seen on the net, and it wasn’t even on a professional site. I screwed up my courage and ventured a response-- claiming to be "a submissive little sissy wannabe who would love to meet the right woman who would train me to be the woman of my darkest fantasies."

Now this was a lie, but on the internet, everybody lies about who they are. I’ve been everything from a "cowboy with very large feet" to a "bored and horny housewife" to a "19 year-old cheerleader looking for my first bi experience." The point is that while I didn’t really have any previous fantasies about being somebody’s sissy slut, it was an exciting idea that seemed to offer a great deal of promise.

And like I said, I’d been drinking.

I responded to a few more personals and then left to go check out some other porn sites. In the spirit of the first ad, I browsed some bondage sites and found that I quite enjoyed the women who were trussed up, helpless to resist the staggeringly huge cocks that came at them from both fore and aft. I was hard and jerking off in no time.

One girl in particular caught my fancy. She wasn’t a porn beauty, just a plain Jane with a mouth full of cock. But what really caught my eye was her hair, which was sticky and matted with what seemed to be gallons of cum. The caption read "Wendy-whore enjoys her 50^th cock of the night." Looking in her glazed-over eyes, it was easy to believe that the caption wasn’t exaggerating.

I sat there imagining myself as one of the faceless men who would show up to give this Wendy-whore the semen she craved. Perhaps there were so many of us fighting to use her constantly stuffed-full mouth, pussy or anus that those of us too horny to wait just splattered the girl with our cum as we jacked off to the sights and sounds of her never-ending sexual service.

And then I thought of MissKriss666 and my fantasies took a different tack. What if this woman was really one of her harem of sissy slaves, trained and transformed into being a cum-starved Wendy-whore with a live Internet feed? I imagined myself in her position. What would it be like to service 50 men in one night? Could it even be done in one night? What if I was turned into a sissy slut who had to go weeks, servicing a never-ending parade of horny men, never knowing who was watching me out in cyberspace?

I was as excited as I could ever remember being, and as I downloaded Wendy-whore’s picture I shot my load right onto my computer screen.

Now I’m always careful around my equipment, but Wendy-whore made me so Wendy-horny that I just didn’t care. Plus, I liked the sight of my seed dripping down her face along with the rest.

I was just recovering my senses when my browser gave me an instant message. It was MissKriss666. My hands were still sticky, but I responded immediately. She told me that she only answered queries with an attached photo and phone number, and if I was serious about being her "sissy-fantasy wannabe come to life," I had better send an appropriate picture soon.

I have plenty of pictures on file, but nothing that seemed sissy-slut appropriate. Did I mention that I’d been drinking? Well I was also horny again and I soon broke out my digital camera and tripod and decided to take a special picture for MissKriss666.

I’d once stolen a pair of sexy panties from an old girlfriend of mine. I’ve beaten off into them many a time, and now I pulled them out of their hiding place and put them on. They had several of my cum stains on them, but they still looked very sexy as I slid into them. And they felt terrific. Why hadn’t I tried them on before?

I started rubbing my body, and especially my rock-hard penis through the pink lace material. I was ready to explode again when I had an idea. I hit the self-timer on my camera, and then took a picture of me in my panties. I then pulled out my razor and proceeded to take a picture of me shaving my chest. I took another shot of me shaving my legs, and yet another of me giving my balls a careful once over. I didn’t have any nail polish, but I did have some glossy model paint, so I took a picture of me with newly painted brick red toenails.

All this time I’d been sipping brews, and now the empty beer bottle seemed like a perfect fit for my asshole. Using some petroleum jelly, I lubed it up and stuck the bottleneck up into my acepting ass. I smiled brazenly as I took another picture.

It felt really good, so I fucked myself with the bottle while I masturbated in my pink panties. I fantasized about sucking a monster cock, and when I was close to orgasm, I hit the timer on my camera and was proud when I shot my load just as the camera clicked off another picture. I was so excited that my cum hit me in the face, and I was immediately reminded on Wendy-whore. I set up one last shot, me in front of the picture on my computer screen. When the camera went off, I was licking the cum off my face, and I had the same glazed-over look in my eyes as the picture on the screen behind me.

I downloaded the pictures and attached them to my reply to MissKriss666. For some reason, I opted for honesty, and I wrote in my reply that I was actually a novice, but after finding this web site I hoped that MissKriss would someday turn me into her own personal Wendy-whore. At that point I was serious, and after I sent the note along with my home phone number, I masturbated once again, fantasizing about being a cum-drenched sex slave like Wendy-whore.

When I came, I licked up my ejaculate just like Wendy-whore would have. And then I fell asleep in my pretty pink panties. I never bothered to clean the cum off of my computer screen or even brush my teeth.

That night I had some rather intense sex dreams. I was a sissy sex slave, desperate to satisfy a never-ending line of horny men. Whenever I slowed down my fevered cocksucking, MissKriss was standing nearby to prod me on with her whip. Thus motivated, the men shoved their cocks into me from both ends, and it was all that I could do to gulp down their endless torrents of cum. In my dream, I had a monster cock buried balls-deep down my throat, another stretching out my ass and two more spurting in each hand.

Just like Wendy-whore, my hair was sticky and matted with gallons of drying semen.

I finally woke from my dream right about noon. I had a smashing hangover, but I was hard again and decided to beat off in bed. I was just about to have my first orgasm of the day when the phone rang. I kept stroking as I picked up the phone, and I had a hard time catching my breath when a harsh voice asked if I was the sissy slut wannabe. It was MissKriss, and after I meekly answered in the affirmative, she asked why I hadn’t driven in to Dallas as she had ordered me to do in her last e-mail.

Somewhat confused, I apologized and explained that I had fallen asleep around 3am. MissKriss barked that "sissy sluts don’t have the luxury of sleep," and if I was serious, then I had better be at her house by 6pm, or I would miss out on my best chance to become the sissy slut of my dreams.

She hung up abruptly, and I was so startled that I lay in bed for a few minutes wondering if I really had the nerve to go through with the fantasy that had been so powerful last night. I wasn’t drunk now, but that image of Wendy-whore seemed to call out to me. I couldn’t explain it, but when I logged on and saw a picture of MissKriss, completely naked and whipping one of her slaves who was wearing a maid’s outfit, I knew that I had to go to Dallas and meet this woman.

She held the answer to all my sexual fantasies.

I jotted down her address, and shivered when I read her instructions. I was to drive to Dallas immediately, strip and wait on her doorstep, naked except for the handcuffs and blindfold that she would leave on the stoop for me. I was scared, but also very excited. Finally, I was going to graduate from cybersex to sex with an actual human being. I immediately showered, pulled on my panties and jumped in my car.

All the way in to Dallas, I kept thinking about MissKriss, and my cock throbbed non-stop at the fantasies that filled my torrid imagination. I opened my fly and slowly masturbated while I drove, carefully never coming to the point of orgasm. Somehow I knew that I would be punished if I came before MissKriss allowed me to.

Two hours into the drive, I was so horny that I had a hard time keeping my eyes on the road. I knew that I had a few hours to spare, so I pulled over at a rest stop and tried to calm myself. It was no use. Finally, I decided to use the restroom and relieve my aching balls. I went into the bathroom, found a deserted stall, dropped my pants and started to beat off.

It only took two strokes before I was about to ejaculate, but I suddenly stopped when a man came into the restroom and entered in the stall next to me. I froze mid-stroke, certain that if I moved a muscle I would moan out and shoot a stream of cum right over the stall wall.

I was breathing pretty hard, and it wasn’t difficult for the man to guess what I was doing. After an eternity of tense silence, a strange voice whispered "don’t stop. I’ll join you."

I was shaking in fear, but I was also too aroused to care. Something snapped in me, and I quietly responded. "I’m sort of new to this," I said, "but right now, I’d really like nothing more than to suck your cock." There was a moment of silence, and I thought that maybe I’d gone too far and this guy was going to beat me up or call the police or something. But then I heard him zip up his fly and he said. "It’s the blue and white RV at the far end of the lot. Wait five minutes and then come on in if you’re serious."

He stood up and left

I started to hyperventilate. What the hell had I gotten myself into? I’m not gay, and had never even considered having sex with a man before. Now all I could think about was going down on this stranger, slurping up his cum and then licking his cock and balls until he was hard enough to savagely rape my virgin ass.

Something was wrong. I only drove out here because I wanted to have sex with MissKriss. If she wanted to strap on a dildo and use me like her own sex-slave, well that was hot. But actually having sex with another man was another thing all together.

I couldn’t go through with it. With shaking fingers I zipped up and decided to head home and forget all about MissKriss and Wendy-whore and strangers in rest stops who wanted me to suck their cocks. I told myself that cybersex would be enough for a small town boy like me. I took a deep breath and left the restroom. I had my head down as I returned to my car, and I hadn’t noticed that I was parked right next to the blue and white RV on the end of the row.

I stopped short when I realized how close I was, and I gulped and tried to quietly unlock my car. Then a soft voice came through the window. "Aren’t you coming in?" it asked. My cock sprang to attention. My penis wanted to go in, but I couldn’t get my voice or feet to respond.

Through the curtained window, the stranger told me to relax. He had a very soothing voice, and because I couldn’t see him, I soon found myself leaning on my car, telling this unseen stranger all that had happened over the past 24 hours. People passing by surely must have thought I was mad, talking quietly to myself by the side of the highway.

We talked for quite a while, and the soothing voice convinced me that there had to be something to my Wendy-whore fantasies because he could see my cock straining to break free of my trousers. I admitted that the thought of sucking him off was making me very horny, but that I was also scared and didn’t want to do anything that was "gay."

A new, feminine voice shocked me when it suddenly broke the silence. "Sweetie, It’s not gay for a woman to make love to a man," the woman’s voice countered. "I can tell you really want this, so here’s what I suggest. I’ll send my husband off while I turn you into the woman of your dreams. When he gets back, there’ll just be two horny women waiting in the RV. If you’re still not comfortable, you can go on and I’ll take care of my hubby by myself."

What do you think?" she asked.

I thought long and hard, and then took a deep breath and softly agreed. I almost came in my pants when I whispered "yes."

I could hear the door open and somebody went off for a long walk in the woods. Then, as I sat motionless on the other side of the RV, a rather good-looking woman came around to me. She was probably 40, and had short red hair and very large breasts, which I noticed immediately and wondered what it would be like to be blessed with a rack like hers. She smiled warmly and kissed me on the cheek. With an arm around my shoulder, she led me into the RV.

Her name was Denise, and she brought me a glass of wine to calm my nerves. After a few moments to get comfortable, she had me change into some of her clothes. She had a pink bra that almost matched my panties, and she stuffed the DD cups with some washcloths. It didn’t exactly look convincing, but my erect penis was more than satisfied.

She noticed this and laughingly said "we’ll have to do something about that or you’ll never pass for a woman." She slowly took my penis in her hand, and was bending down, presumably to give me a blowjob, when I suddenly shot my load all over her.

I was mortified, but she just laughed and said that it was proof that we were doing the right thing. I had to agree, it had been one of the most powerful orgasms of my life, and I could tell that there would be another as soon as her husband returned from his walk.

Denise scooped some of my seed off of her blouse and took a taste. She smiled, and then looking straight into my eyes, she fed me the rest of what had splattered over her clothes. "Do you like it?" she asked. I moaned "yes" and she smiled. "Wait until you get a taste of Bill. You’ll love it," she said.

We cleaned up and Denise gave me a pair of pantyhose to shimmy into. She showed me how to ball up the legs so I wouldn’t get a run in them. Next came a skirt and blouse that were a little tight on me, but I sucked in my breath and managed to get into her clothes. I knew that I wouldn’t be wearing them for long.

Denis pulled out some makeup and did my face. She took a long time, getting everything just right. Then she started brushing my hair into a puffed up feminine style. I already have long hair, so it actually came out looking pretty good.

When she finally pulled out a mirror, I was amazed at the transformation. Don’t get me wrong, I’m a guy and didn’t look very convincing as a woman. But Denise had turned me into a sexy drag queen, and my cock stirred immediately in my panties.

Throughout all of this, Denise was getting rather excited. I could tell by her breathing that she needed some relief soon, and I impulsively reached out and started rubbing her legs. She moaned and immediately pulled up her skirt and parted her thighs. She wasn’t wearing any panties, and I plunged my fingers into her sopping wet sex.

Just like me, Denise came very soon after I started finger fucking her. But unlike me, she wasn’t satisfied with her orgasm, and she pushed my face into her wet crotch. I was in heaven, licking away in ecstasy. Denise had snaked her hand into my panties while I serviced her pussy like a man possessed. I was ready to explode again when I suddenly heard the door open up behind me.

I froze, but Denise squeezed my balls and I quickly resumed running my tongue up and down her slit. I heard Bill’s zipper as he dropped his pants and moved around to my front. Denise reluctantly pushed my face away from her crotch and I came face to face with my first cock. It looked huge, but with Denise’s urging, I wrapped my lips around the head and started bobbing up and down on it.

I decided to try and deep throat Bill’s cock, but I started to gag. Just then Denise slipped a finger into my asshole, and I was so turned on that my gag reflex shut down and I soon felt Bill’s balls slapping against my chin.

I was in heaven. Wendy-whore would have been proud of the energy I put into sucking Bill’s cock. Even though my jaw was getting a bit sore, I never let up. Besides, Denise had one, then two, then three fingers lodged firmly in my ass to keep me motivated.

Suddenly Bill’s cock began to twitch, and I instinctively knew that he was going to erupt. At the very last moment, I pushed him out and let him shoot all over my face like my favorite porn stars do. It was amazingly erotic, especially as the cum dripped down into my mouth and Denise continued to fuck my ass with her fingers. Suddenly I felt faint, and I almost blacked out as I erupted once again into my panties.

I knew then and there that I would gladly give anything to keep having these mind-bending orgasms. I would gladly become Wendy-whore to keep this fantasy alive.

I gathered my breath and I looked up at Bill. He was a pretty handsome guy, and he looked so sexy cuddling on the floor with his wife. They were making out, and I realized that Denise had been ignored for too long. I shimmied up and planted my mouth over her sex and she tensed up as I set about pleasing her.

Soon Denise was on the verge of another orgasm, and Bill was getting aroused as well. I stopped licking Denise only long enough to beg Bill to "fuck me," and then I went back to teasing her clit.

Bill chuckled as he lifted my shirt and ripped aside my cum-soaked panties. He spat on my exposed asshole, and slowly eased his now erect cock into my nether passage. Oh my God, did this feel good! I had turned into Wendy-whore as he plowed my ass and Denise squirmed on my face.

He tensed and shot his seed deep into me just as Denise suddenly let loose with an ear-splitting scream. We all collapsed in a heap on the floor, my nose still buried in Denise’s sex and Bill still lodged in my ass. We lay there panting for what seemed like hours. Finally Bill pulled out of me with a pop, and he chuckled. "See, I told you that you’d enjoy this."

I had to agree.

We finally pulled ourselves together, and I realized that I would have to leave soon if I wanted to be at MissKriss’ doorstep by 6pm. Denise helped me clean up, and I could tell that Bill was ready for another round. But I was late, and Denise promised to take care of her husband so that I could make my appointment on time.

We exchanged phone numbers and I was delighted to find that Denise and Bill lived rather close to my home. Deep tongue kisses followed, and I reluctantly pulled myself away and decided to hit the road.

Once again, I had visions of Wendy-whore filling my head as I drove toward MissKriss. Just outside of Dallas, I had an idea. I pulled over and took off my pants and shirt, which I tossed into a nearby garbage can. That’s how I drove into Dallas wearing only a pair of cum-soaked panties, with my cock peaking out of the top. I almost hoped that a cop would pull me over, so that I could give him a blow job in order to get out of a ticket.

But I made it into town without incident, and ultimately it wasn’t hard to find MissKriss’ address. By 5:30 I found her house, and checking to make sure that the coast was clear, I ran up the walk and collapsed on her stoop.

Once again I was shaking as I opened a waiting paper bag with my name on it. I removed a blindfold, buttplug and some handcuffs. Before I could stop myself, I had discarded my panties, shoved the plug into my still-sticky ass, fastened the blindfold and handcuffed my hands behind my back. I lay shivering on the doorstep, relieved that there were plenty of bushes to hide me from the street.

But I was also a bit sad that men passing on the street wouldn’t be able to see me and stop by for a quick fuck.

An eternity passed before the door finally opened and the woman whose voice I recognized as belonging to MissKriss stepped out onto the stoop. Silence and I held my breath, not knowing what would happen next. "I didn’t think you’d show," she said. "By the time tonight’s over, you’ll probably wish you hadn’t come."

With that she grabbed my hair and dragged me into her house.

Once again I thought, "What have I done?" And once again something inside me welled up. In a clear voice I said "Mistress, do whatever you want to me—just turn me into a sissy slut and I’ll do whatever you ask."

MissKriss laughed and said, "Don’t worry Wendy, you’ll soon be living out all your fantasies…"

"And more."

 

 

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