It all started while I was fucking Janice, who I had met at a local pickup spot. I was banging away at her pussy, which frankly was not the tightest I had ever been into, when she started fingering my asshole. Tentatively at first, then when I did not complain, more boldly. At first I found it merely distracting, as I was trying hard to come and finding it just out of reach. She had already come twice and was probably getting tired of my inability to get off. She slipped her hand between us, scooped up some the slippery fluid I had fucked out of her, and massaged that into my asshole. It felt good.
Soon she had slid her finger into me past the first knuckle, and it felt even better. She whispered, "I want your cock there," and I froze in surprise for a moment. Then I pulled out of her sloppy cunt and directed my cock to her asshole. As I started to push into her, she shoved her finger all the way into my ass and I erupted in a blinding orgasm, I guess some of which probably went up her ass but most of which went all over her crotch and into the sheets. I collapsed, she slithered out from under me, making disgusted noises, wiped herself off on my best shirt, got dressed and left.
Over the next few weeks I just couldn't get the memory of her finger going up my ass, and me instantly coming, out of my mind. I knew I wanted more of that action, but didn't know how to get it. No woman had ever even tried to touch my asshole before, and I didn't see how I could ask for it. Then while browsing an online toy store, I noticed the "Anal Explorer Kit." I immediately ordered it and impatiently waited out the days until it was delivered. The day the package arrived I felt as nervous as I had on my first date with a girl who was reputedly "easy."
My heart thumping with anticipation, I took the kit into the bathroom and opened it. Inside were a vibrator and three separate attachments, ranging from pencil size to the size of a healthy cock. I fitted the small one to the vibrator and lubricated it with KY, hastily stripped my clothes off, and slid it into my eager asshole. It felt very nice. My cock rose and began to leak pre-come as I worked the vibrating probe in and out of my tight hole. Soon I began to crave more, and switched to the medium size. After just a few minutes the big one took its place, and I was in heaven. I came three times before regretfully stopping to clean up the mess and put my new toys away. My legs were shaking so hard I barely made it up to my bedroom, where I dreamed of being fucked senseless by an anonymous throbbing cock.
Over the next few weeks I fucked myself many times with the Anal Explorer, but found it increasingly less satisfying. I bought several larger, more realistic dildos and used those too. I also got a vibrating butt plug and sometimes left it in when I went to work. It was all fun and exciting, but I wanted more. I knew that nothing would satisfy me but a real cock fucking me hard and deep, until it spurted its hot load deep inside me.
But how was I ever going to make this happen? I started checking out guys at work and on the street, wondering if they were gay. I couldn't make myself feel attracted to any of them. I watched some Tranny movies; fucking my asshole with a big dildo all the while. If only I could meet a girl like that....all the pretty female parts but with a big hard dick to fuck me. But where do you find one? No idea.
One night, in desperation, I searched out a gay club and went in. The place went silent as I approached the bar. Eventually one guy asked me straight out if I was a cop. Even as I answered "NO!" I could tell that he didn't believe me. After an hour or so I went home, jacked off, and went to bed. I dreamed....not of meeting a beautiful transvestite, but of being one! I woke up, my heart pounding with excitement, and spent the rest of the night making plans.
It wasn't easy, but as the weeks passed I assembled my feminine wardrobe one piece at a time, practiced walking around the house in high heels for hours, taught myself make-up tricks, and all the rest. Luckily I have a slender build, am not very tall, and my legs are quite presentable when carefully shaved. I rehearsed in front of a mirror until I had all the feminine gestures and my adopted little-girl voice down pat. I took a few short trips to the gas station, then the grocery store, then the mall. Shopping at Victoria's Secret got a hell of a lot easier, and I began tentatively flirting with men from time to time. If anyone was suspicious, they sure didn't make it obvious.
At last I couldn't put off the big night any longer. I began final preparations by rinsing my asshole out thoroughly using an old-fashioned douche bag. As the warm water filled my bowels I imagined hot come spurting into me. I rinsed myself out three times and then squeezed a small tube of KY into my asshole, hoping it would be enough to lubricate me throughout the vigorous fucking I hoped to receive. I dressed with care after a leisurely bath, slipped into my spike heels, and called a taxi.
When the driver saw me, he jumped out of the cab to open the door for me. I saw him gawking at my silk-stockinged legs as I gracefully slid into the cab. I smiled sweetly and adjusted a bra strap as he closed the door. As he walked around the cab to the driver's side, I saw him uncomfortably trying to adjust his swelling cock. I was a success already!
He left me at the same club where I had picked up cow-cunt Janice so many months before. I hesitated just inside the door. Would anyone recognize me? I looked around, and saw naked lust in two dozen pairs of male eyes, and naked resentment in as many pairs of female eyes. So far, so good.
The place was fairly crowded, and I didn't see any place to sit. Then a big swarthy guy rose up out of a corner booth and beckoned to me. Shit! Did I know this guy? Did he think he knew me? With trembling knees I walked over to him, wondering if it wouldn't be better to just turn around and leave.
"Lookin' for a place to sit?" he leered. He was more than a little drunk.
Reluctantly, I nodded. "Baby, as long as I have a face you'll have a place to sit," he shouted. His friends cheered. I glared at him and started to turn away, but he grabbed me around the waist and settled back into the booth, pulling me down onto his lap. His friends cheered and clapped even louder. As I squirmed against him, trying to get back on my feet, I felt his massive cock poking into my thigh. It was hard, and it was hot. Wasn't that what I was here for?
"What are you drinkin', beautiful?" he whispered into my ear. I wiggled against his cock again, imagining it sliding into my eager asshole. "I think I'm in the mood for something...hot," I whispered back. His eyes grew larger. "Hot and salty," I continued huskily. Just in case he didn't catch the hint, I casually dropped my hand onto his thigh and let my fingers graze the thickness of his cock. I was actually touching a real live cock!!!
I tortured him for about a half hour, until he rather pitifully begged me to go with him out to the parking lot so he could "show me his new car." How I ever tottered out there with my knees like water I don't know, but then we were there and he was pushing me up against the car, which was NOT new, and not even very nice, and slobbering all over trying to kiss me, which I really did not want to do, and it was all getting out of control. When I could catch my breath, I took a chance and just told him, as cold and tough as I could make it sound, "Look buster, I know what you want, and you need to know what I want. I don't want romance, and I don't want bullshit. What I want is a hard cock, and I want it NOW."
That took the wind out of his sails, and the thick cock pressing against my belly even began to shrink a little. I rubbed it a little through his pants and it revived though. Then somehow he was sitting on the front seat of the car with his legs hanging out and I was trying to unbuckle his belt but my hands were shaking so bad he had to help me and then I was holding the biggest cock I had ever seen in my hands. God, it was a monster, bigger than any of my dildos and I knew I couldn't go through with this after all. I really wanted to just run away, but it was kind of late for that, so I stroked it just a little as well as I could, and started to think up excuses. But what the hell, as long as I was there, why not just suck him off? I milked his cock until a drop glistened on the end of it, then lowered my face to it and licked it off. He groaned and thrust his hips at my face. It seemed natural to open my mouth and take it. And it felt GOOD in my mouth. I couldn't take much more than the hot, spongy head; I tried, but I just couldn't do it. I imagined that thing ramming into my inexperienced asshole and shuddered. I tried jerking him off into my mouth, but it wasn't going to work and we both knew it. I could tell he was getting frustrated enough to try to rape me, and I had to maintain control at all costs. I coated his cock with as much spit as I could work up, and stood back.
"You just lay there," I ordered. "I don't want you on top of me, and I don't want you to split me in two with that huge deformed thing. We're going to do it my way, or not at all, got it?"
I turned my back to him, lifted my skirt, and pulled my silky panties to one side enough to expose my asshole. Thank God it was dark out there. I grabbed his cock with one hand and put the slick head against my starfish. Hot and cold flashes racked my body as he began to invade my virgin orifice, stretching me beyond any limits I had known. After an eternity, the head popped in and the pain eased. I lowered myself gingerly onto him, stuffing myself with his hard meat, until I was sure that I had taken it all. I then tried to move away, and found that I was too weak to move at all. I sobbed in frustration and he grasped me firmly by the hips and thrust into me to the hilt. So much more than I had imagined! I was impaled on this huge pole, and all I could do was wiggle around weakly on it. I wanted to be fucked!
I regret that I cannot remember all the details; I was nearly delirious with the new sensations racking my body. Somehow he managed to get up from the front seat without disconnecting from me, and somehow I found myself bent over into the car, with him behind me, plowing me vigorously while I wailed in joy and pain. How long it may have lasted, I have no idea. It may have been minutes or it may have been hours. At some point my shaven cock and balls slipped free from my panties and I was jerking myself off as he violated my ass, and I became aware that his cock seemed to be getting even thicker and longer, and his strokes more savage, and I imagined all that hot come erupting into me, and then I was coming, and coming, and coming onto his car seat and then he gave one last mighty thrust and jetted his load right up my ass.
I cried when he pulled out of me, I felt so empty, and I was sore and hurt all over but I didn't want it to end. I guess I was still crying when he put me in the cab. Somehow I got home though, and when I looked in the mirror my makeup was all streaky and such a mess, and my dress was ripped and I had come running down my thighs. But I was smiling. I had done it. I had sucked a real cock, and gotten fucked in the ass. And I had liked it.