Why I Started Masturbating With Anna

I read the first story on Solo Touch about six months ago and I have been enjoying many since. Solo Touch has also helped me with many great orgasms since then. I want to share the first time I had with my best friend Anna. Here it is as I remember to the smallest detail.

Going back to my later days of high school my best friend was Anna. We both attended a private girls only Catholic school in our town that serviced many surrounding rual areas and smaller towns.

We became very close since the first year of high school and shared everything together. Anna was one of the best friends I ever had and still to this day I meet up with her about once a year.

We were good girls but not angels. We would bend the rules trying not to break them.

Anna was a bit more daring than me and she was at times the one to start anything that was on the naughty side.

We talked about boys and sex, our bodies and masturbation too. We would often talk about sex and how we would masturbate when alone and also about how often we did it. Although we talked about masturbation, we never did it together. We skinny dipped once and played strip poker one night but never masturbated in front of each other.

This story is what changed our lives and although it was nasty at the time it happened, it brought us closer together as great friends.

Grade 11 was coming to a close and we had a hot spell for a few days. Anna and I walked up town after lunch one Friday for a break. While at the store we grabbed some drinks. As we walked back to school Anna said she did not want to go to the next class. I knew we should with such strict school rules so I said we should just go back.

With a snarl Anna walked back with me. Once we were back on school property she pointed out that we were a few minutes late and could wait until next class to go back. We knew we would get detention after school but we would for being late anyway so we skipped off the next class.

Anna and I walked out behind the school through trees and into a small private cleared area. The day was hot and we both layed back on the grass.

Anna sat up after a few minutes and without saying a word pulled off her school top followed quickly by her bra. She turned to me laughing saying she was hot and this was the worst thing she had ever done on school property. She laid back down with her hard boobs pointing straight up. She turned her head to me and said what are you waiting for. I laughed too and quickly joined her, baring my breasts. Mine were much smaller than Anna's. She had wider hips and much bigger boobs. As we both laid back down we laughed about the detention we would get after school and how it was 10 minutes less than the class we skipped.

A few seconds later things changed. We heard a voice telling us to stand up right now! It was Sister Crann. She was the head Sister in our school and we both knew we were busted bad.

She told us to instantly dress ourselves and marched us back into the school. We were directed through a few doors then to the waiting area outside her office. She then asked who started this and Anna said it was her. Sister Crann pointed at me to sit down and Anna to go into her office.

As I sat in the small waiting area I could hear talking but could not make out the words. Every now and then Sister Crann would raise her voice and could hear her then. All I could get from the conversation was something about our parents finding out. I was very afraid that my parents would be told I was half nude sunbathing with my friend. I was certain I would never be able to see Anna again.

After about 10 minutes of conversation the room went quite. I heard what sounded like furniture moving over the hardwood floor for a few seconds.

I slid closer to the door now and heard a few more muffled words. Then after about 30 seconds of silence the silence broke with a large crack followed by Anna's crying out very loud. Sister Crann was known for her caning if you stepped out of line too far. I never thought she would cane her for this! A second crack came followed by more cries from Anna. I sat there as each crack of the cane came down knowing Anna was getting it hard judging from her cries getting louder now. I shook with fear as I counted the cracks. Sister Crann left about 10 seconds between each one. As soon as I heard Anna get just a bit quiet from crying the swish came with a sharp crack then she would cry out again.

I counted 30 strokes of that cane thinking it would never end. Once the caning was done I heard Sister Crann softly talking and I could just hear Anna crying but not so hard. The room got quieter then I heard Sister Crann talking again.

I heard footsteps so I sat straight up in my chair like I heard nothing at all. The door opened and Anna came out first with a red wet face and quivering lips. Sister Crann motioned her to stand in the corner of the waiting room. She then turned to me telling me to step into her office. With fear I walked through the door. I thought I may be off the hook since it was Anna that fessed up to starting the whole thing but I was wrong.

Sister Crann asked me if there was any reason she should not contact my parents and if they would understand why I was laying half nude in the school yard with Anna. I begged her not to tell them. She said I must also be punished. I thought I was getting many detentions until she said I was getting 20 strokes of the cane. I had only ever been spanked with a hand before so I had no idea what I was in for. I instantly started to cry just thinking aboout the caning.

Sister Crann pointed to the chair she had moved in place for Anna and said I was to drop my skirt and bend over the chair holding onto the seat. With tears running down my cheeks I slid my skirt down and it hit the floor. I bent over and she said to me, undergarments too, in a sharp voice. She said I needed to feel the full impact of the cane for what I had done.

Now I felt very ashamed with my bare ass waiting to be caned. I always thought the bad girls got it on the outside of the skirt. I never knew a girl who got caned before then.

Sister Crann told me to look straight ahead and not to look back and she would tell me when the first stroke was. I'm not sure where the cane was hiding as I never saw it until it was over.

I heard a few footsteps and then she said we would now begin. Seconds later I heard the swish, then the sting of the cane on my bare ass. I cried out very loud on the first one. I could not believe how it stung so hard! A few more seconds and the second one came hard on my ass again! Wow did I squeal out loud and hard! My ass was stinging like nothing I had ever felt before. A few more seconds and another crack of the cane came down hard on my ass! I writhed and twisted my body as I cried out. Sister Crann said I should stop crying and hold still becasue we had a long way to go yet. With all my might I stuck my ass out again then she stroked that cane even harder! I cried so hard I did not make any noise and thought I would never catch my breath. As soon as I managed to suck up a deep breath she stroked my ass again real hard! I thought I would never live through this horrid caning! I know I cried harder than I ever had in my life before.

I lost count but the 20 strokes felt like 100. I thought she gave me more than 20 but Anna told me later that she counted out 20 exactly.

Once the last stroke of the cane was done Sister Crann left me bent over crying for a moment. I was not sure if I was done and when she said to pull up my underpanties and skirt I was so relieved.

As I pulled them up it was very hard to get them over my stinging ass. My ass felt like it was on fire! I gently pulled them on then walked slowly with Sister Crann out to meet Anna. Anna was still crying from her ordeal, and from hearing me get the cane.

Sister Crann told us both to go to the washroom to compose ourselves then off to our next class. She told us she never wanted to see us in there again and if she did it would be double for us both.

I knew I would never see that room again!

As we walked to the washroom we said nothing at all. We both just whimpered then once inside we found nobody there and we hugged and cried together.

The same weekend we got together as normal but we were a little quiet now. We had decided to go to the town pool for the day because it was quite hot. My mom dropped me off at the pool and I was to walk home later. I met Anna and we made small talk as we walked in to change. As we were getting changed Anna dropped her shorts down and I gasped! Anna I said. You have huge red cane marks on your ass. I told her she could not go out like that. She said let me see yours so I pulled my shorts down too. Anna also said I had the same on mine. We pulled up our clothes and walked out to the street. I asked Anna what she wanted to do and she said lets walk to the end of town to the small river that was there. It was not very wide but it was very private most of the time.

We walked and now started talking about our caning. We both agreed it stung a lot and we talked about how much we cried too. As we got to the stream we found nobody was in sight at all then Anna said Sister Crann can't stop us now and started to strip off her clothes. I laughed real hard and took my clothes off as well. WIthin seconds we were both naked standing in the sun. Anna turned her butt to me saying look at my poor ass. I did the same then I said we should go in the water.

The water was cool with the little stream running fast. Anna dipped her ass in saying it felt good. As she stood up I noticed her nipples were now really long and hard. I commented on them and she said mine will be the same once I dip in. I sat my ass in the river then splashed the cool water all over my body. I stood up revealing nipples that I thought would break they were so hard! Anna said I told you so then we lay down on the bank of the river.

Anna started asking me more about the caning day. She said even though it hurt so bad she now kinda looked back on it as a bit of a turn on. She confessed that she had even masturbated a couple of times while thinking about Sister Crann caning her bare ass. She then asked me questions about my punishment. She asked if I got it on the underpanties or the bare ass like she did. She asked if I watched the cane hit my ass and a few other things. This started to make me feel very erotic and horny for reasons I did not know. I told Anna that I was getting horny now too. Anna started to talk more about her body and about mine. She gave me reasons to show her pussy inner lips to me asking if mine got larger when I was excited and is it normal.

After a few more minutes Anna asked me if I wanted an orgasm. I said I could have a few right now. Then she said we should masturbate together right then and there. I was very horny and agreed it was a great idea.

Anna stood up and after looking around said nobody was there and we could start now. I was so horny and wanted to orgasm real bad! I said we should go back to the edge of the river. There was a spot that was eroded in a half circle. We sat our butts in the wet sand and leaned against the earth. We both opened our legs and then I was the first to dip my finger in my wet pussy drawing out some slippery juice to rub my clit with.

Anna followed doing the same and for the first time since we met we were both masturbating while watching each other.

What a nice feeling it was to rub my clit while my best friend did the same. About four or five minutes went by then I started to feel my orgasm climbing. I looked Anna straight in the eyes and said I'm going to start cumming real soon. As my breath got shorter and faster my chest started to move up and down faster and I did not break eye contact with Anna. I felt my orgasm getting closer and closer as I leaned back arching my body. I straightened out like a pin squeezing every muscle in my body as I slid back still not losing eye contact. I came hard fingering my clit as I watched her eyes grow large watching me cum. Shortly after that she too had a great orgasm while I watched her wiggle around. We took a short break and then continued masturbating to a few more orgasms each. It was about the best time I ever hard masturbating. Doing it with my best friend was so fantastic!

This was the first of many masturbation times we had together. Now when we get together we talk about those days and continue our mutual masturbation. Our caning started a lifetime of pleasure and I'm sure it made us closer as great friends.

We are both married now. I hope to see Anna again in about two months. I think I will tell her about this website, and tell her to look for a very special story that she will remember.