Chapter 2: Masturbation

Now it is the last weekend at school. I should have been studying for finals but when the e-mail arrived asking me if I was interested in another escort I couldn’t turn down the opportunity. The guy’s description showed he was fifty years old which would make him the oldest man to ever fuck me. He was married of course and had four kids, all older than me. Ralph was from Chicago and was in town for business but wanted someone in the evening to entertain him. Well, I was ready to help him out!

Friday finally came. Luckily my schedule on Fridays is easy with only one class and that being in the morning. Thus I had the afternoon to get ready for the evening to come. Karen was not so fortunate and so I also had the room to myself which came in handy at times like this. I got back to my room after a light lunch and plopped down in my bed. All I could think about was what would happen later that night. What would he be like? Where would he want to go? Would he treat me nice?

Then of course came the other thoughts ... Would he feel me up right away or take his time? Would he want me to do anything to him at the restaurant or wait until we were back to his hotel room? Would he have a nice cock? How would he smell and taste when I sucked it? I dreamed of him fucking me and wondered if he would cum in me or want to spray his sperm all over me?

The more I thought about having sex with this stranger the warmer my pussy felt. I lifted up my tank top and played with my breasts, the nipples already pointed and hard from my dirty thoughts alone. I loved to play with them and when a man squeezed them gently and grabbed my nipples between his fingers my entire body would tingle with pleasure. I cupped my breasts with my one hand as I used the finger on my other to trace small circles around the nipple.

After spending my teen years hating them, I loved my breasts now. They use to be so small that I was always a bit embarrassed when I was around other girls my age or younger who were so much more developed than me. Now they were large enough to fill out my bikini top and show plenty of cleavage but not too big that they hung down and needed a bra to lift them up. I could still not wear a bra and my boobs would be nice and high with a firm bounce to them.

As my thoughts grew more intense I unsnapped my jeans and lowered them to my ankles, kicking them off to the end of my bed. Lifting my top over my head, I threw it down to join my jeans leaving me to lay naked on my small bed. I spread my legs wide apart and place my hand between them, just covering my pussy and feeling the warmth radiating from it.

I usually shave every day but knowing my plans for the night I had not done it this morning, figuring I would be doing it just before going out so my pussy would be as nice and smooth as a twelve year old virgin. I found that so long as I shaved it every day that it would stay that way but if I let it go and grow that after I shaved it would be red and irritated for a day or so afterwards, not exactly the sexiest look in the world.

So now as I touched it I could feel the slight stubble warning me it was overdue. I really had no choice but to keep it shaved with the clothes that I wore. Some girls I knew liked to keep a “landing strip” or small triangle but I liked the little girl look - bare and smooth. Almost every guy I fucked liked it that way too. I think they liked that it made me look so much younger, like a young teenager.

My finger began to press into my slit as I started to rub my pussy up and down. I was already getting wet so my middle finger easily slid into my slit between my pussy lips. I touched my clit and shivered as it reacted to the stimulation. I loved to be touched and fondled all over my body but when it came to the bottom line, the most sensitive spot on my body was without a doubt my clitoris. When it was hard and sensitive I never ceased to be amazed how such a small spot on my body would make the rest of me feel so incredibly good. My hood pulled back as I ran my fingers around and over it. Now and then I would reach down to get more wetness from my pussy and then go back to my clit.

I took my other hand from my boob and pushed my finger into my pussy like a small cock was fucking me. I kept my other fingers working on my clit and I fucked myself imaging it was someone else doing it to me. It wasn’t long before my orgasm began to start as I felt my entire body began to catch fire as it always did whenever I came. Every part of me from my toes to my scalp began to tingle and feel like it was burning up as my pussy pulsed out wave after wave of orgasmic pleasure. Each wave would radiate from between my legs and flow up and down me like an ocean wave.

I gasped as my fingers worked feverishly to keep me going, not wanting it to end. I arched my back and lifted my hips up off the bed as if to try and pull my dream lover deeper into me. Finally I pounded myself up and down, bouncing on the bed as though I was being fucked hard. Eventually I was exhausted and just laid there with my finger still in me and my hand just pressed against my clit. I must have laid for half an hour, naked and sweating from my orgasm.