Careful What You Wish For

I thought I knew what I wanted, and I knew it probably wouldn't be easy to find. I set out on my 'mission impossible' with the most realistic expectations I could. It would probably take some time to find the right person to help guide me through this mission, so I needed to get a move on finding them as quickly as possible. I had given this much thought, even back to when my cunt was untouched. I considered about opening up about it before, sharing my deepest dirtiest desire...yet when the time came, I always froze up. I didn't want to be seen as easy, or greedy. Afterall, I was raised to be a lady. But, I felt like I was done being a lady! I wanted what I wanted. What I wanted was a cock in my ass.

It was late on a Monday night and I was reaching levels of desperation I did not know could exist in my panties as I browsed anal plugs, thongs, nipple clamps, and other devious sexual aids. My panties were damp so I knew I was on the right track, but I was unprepared for all the options. Plugs the size of my fist, thousands of types of lube! Where was I supposed to start? It was all too much. I needed to stroke my clit and get some relief. Suddenly it dawned on me: I needed a dom. I needed someone to tell me what to do. Not ask me, not force me, just tell me. A firm, but understanding hand to guide me. But, I'm also shy so it would be difficult to meet up with someone. There was only one answer, Craigslist. The apprehension filled me, but if I didn't do this I may never be filled the way I wished. I had to do it. I quickly threw together some words, posting as soon as my fingers stopped on the keys to avoid losing courage.

First I got no replies...I was miffed. Isn't Craigslist the most well-known place for horny men? Where were they? Where was my dom? A few more minutes passed, and the replies began flooding in. Again I was overwhelmed. I clicked on the first random reply. It was simple, and I could handle the question contained inside

"Are you a female?"

"Yes." I replied.

"Awesome, can I have more info?" Was quickly returned.

More info? This was my opportunity. I needed to put it all out on the line before I got scared or gave too much other information up front and felt like I couldn't turn back. I dove in. I gave a quick generic bio of myself including my age and then unloaded on how I get excited thinking about anal. I was honest that I have heard stories of subs being told to wear a plug all day or do other naughty things, and I wanted that for myself. I even divulged I had never done anything with my ass, not even a finger, and I needed guidance. I hit send. I almost didn't expect a reply. A moment later my phone pinged. My breath caught, and my pussy felt a huge surge. He had responded. "I can definitely help." I couldn't believe this. Still with so little information I wasn't sure he would be totally on board so I begin to explain further. I wouldn't be able to send pictures until I was comfortable, but I promised to always obey. Surly this would be a deal breaker.

To my shock another reply came flying back "Sounds good." From here I was asked to describe my body in as much detail as I could, and was presented with the option to text so it would be faster. Normally I wouldn't do such, but my cunt was begging and it was all I could think about. I gave it up.

Before I knew texts were flying back and forth. He was making subtle demands that were driving my already throbbing clit crazy.

"Describe your pussy clear enough to me so I can picture it."

"Tell me what you are wearing."

"Slide your panties and shorts off for me."

I found myself doing as I was told without hesitation. I wanted this. I wanted him to keep telling me what to do. Even if we were only using words I could feel his presence. I felt like he was watching me shimmy out of my panties leaving them on the floor as I crawled up onto my bed.

"Put a finger on your clit and rub it slowly in a circle." I did. "Don't put it inside yet" I wanted to so bad, but I did as I was told slowly circling my already engorged clit. "Rub down across your lips to your ass. Are you getting wet?" I was. I was so wet I could feel it dripping slowly down across my asshole as I lay on my back with my legs slightly spread. "Don't go inside yet" he reminded me "rub your fingers along the length of your pussy." The desire to impale myself on my own finger was almost unbearable. Finally "Slide a finger in your pussy and rub it around your ass." In my haste to finally be allowed to dip into my drenched pussy I almost missed the end part about my ass. I did as I was told, slowly, unsure of what to expect. It felt naughty. Like I was doing something I shouldn't be. I wanted to stop, but I knew that I wouldn't unless I was told to. This only made me wetter.

As my finger circled my puckering rosebud I was asked to remove my shirt and bra. I felt like a complete hussy admitting that I had not been wearing a bra. I was instructed then to pinch my nipples.

"What finger are you using?"

"My middle finger."

"Slide two in now. Feel the walls of your pussy not wanting to let them go. In and out. In and out..."

I couldn't stop myself. I begin to describe how wet my cunt was. How it was dripping over my asshole. How good it felt, and how I wanted more. I wasn't prepared for what would happen next. What I would be asked. "Are you ready to slide a finger in your ass?" Everything inside my brain screamed "NO WAY!" I had already told him my ass was a virgin. I've never even had a finger pushed against it. But my body begin to scream "YES! YES! I am ready!!" Before I could stop them my fingers were furiously replying "I don't know. I've never actually done it before. I'm not sure if I'm ready." Only seconds passed before I received the text that almost made me cum with two fingers stuffed inside me "Rub some juice around your asshole. Get it nice and wet. You are going to finger your ass tonight." That last line hung in my brain. It wasn't a request. I was being told I was going to finger my ass.

"Roll over on your stomach, with your ass in the air." I hesitantly removed my fingers from my snatch rolling over, and pushing myself up onto my knees and propping myself up on my elbows. Fully exposed. Soaked. Waiting. Wanting. He had already told me what was going to happen, and the anticipation could be felt all the way from my rock hard nipples which were now brushing the coolness of the sheets, down to my cold toes I was flexing out of nervous habit. "Put your index finger in your pussy and get it as wet as you can." I had read porn, and knew it was important to be properly lubed so I dove back in happily. Moving my fingers against the walls of my cunt as fast as I could hoping to soak them thoroughly enough not to hurt my waiting ass.

"Now place it at your ass opening and push your way in, go real slow, in and out a little at a time until you relax and loosen up." His instructions were clear. I didn't need to ask for clarification. He was actually going to make me finger fuck my own ass.

The tip of my finger pressed gently against my asshole as I took a deep breath. Slowly with more pressure I felt my ass start to open for my well lubed intruder. Suddenly the tip slipped in and I gasped. My ass protested squeezing my finger tightly. I couldn't do it. It was just too tight. Encouragement came ringing through "Finger that ass..." I wanted to. I wanted to make him proud, and I didn't want to admit failure. I pushed a little further inside moaning now. "Do you have your whole finger in yet?" "Almost" I replied "It hurts a little." "The wetter the better. Push in a out a little at a time." I felt like he was there commanding me. Watching my finger slip deeper into my ass as I moaned. Suddenly I was knuckle deep in my own ass. "I got it!" I hurriedly texted expecting praise. I got none. Instead I was greeted with another pussy gush inducing text. "I'd like you to finger your pussy and ass at the same time." He wanted me to double penetrate myself. I couldn't do this. My ass was pulsating on my finger, my pussy was dripping, and my clit was completely swollen and more sensitive than I had ever experienced. A finger in my pussy would certainly set me off, and I wasn't ready for that yet. He had not told me to cum. Risking upsetting him I was honest "How? I already want to cum from just wiggling this finger in my ass." It was true, but this is not something I would usually admit. I certainly wouldn't be able to call myself a lady after this. He took pity on me, and I was rewarded for my honesty. "Ok just finger your ass til you cum. Do you have a good angle so you can really fuck yourself?"

I did. I was still on my knees, ass in the air, with one finger plunged deep in me, and phone in my hand to reply. I told him so and began to move my finger in and out my ass again slowly.

"How does it feel? Can you cum with just an ass fucking?"

"It feels really tight and full. I didn't expect my finger to feel this big. I don't think I can, but I can go in and out all the way now."

"I like that. Rub your clit. I want you to cum like an animal."

"My clit is so sensitive."

"Pretend I'm sucking on it and keep fucking your ass. In and out. In and out. Put the phone down and fuck your ass. Cum for me."

I immediately did as I was told leaving the phone where I could see any texts I may get while I fucked my ass and rubbed my swollen clit.

"Fuck that ass, cum for me baby." I moved my finger faster inside my ass.

"I want you to explode." My finger furiously moved over my clit.

My moans became louder, and my hips began to move on their own as my ass and finger slammed into each other. It still felt deeper and bigger than I thought my own finger would, but I was getting used to it, and starting to enjoy it. I could really feel my ass start to open up when all the sudden an orgasm began to build low in my abdomen. I was going to explode. "Cum for me." I couldn't hold back. My ass clamped onto my finger pulsating as my pussy released gush after gush of juice down my shaking thighs. My clit screamed with pleasure and pain and I was forced to release it as I finger fucked my ass through my orgasm.

I didn't feel like my body could move, and I thought I would cum again as I pulled my finger out of my now destroyed ass. "Thank you. That was exactly what I needed." I texted as I pulled a blanket over myself.

"You are welcome. I will contact you tomorrow morning and tell you to take off your clothes. You can, and will?" It wasn't a question, but I replied anyway "Yes."

"Good. I will figure out something you can insert in your ass tomorrow."

I wanted to protest, but after such a good first ass fingering I was excited for what could come. I drifted off to sleep feeling wet, used, and suddenly quite empty dreaming that my new ass master would stay true to his word.