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Learning a Lesson

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by Amy Davis It was a warm fall day with the birds chirping and the sunlight streaming through the dorm room window. Things could not be more perfect except I was depressed. It was my first semester of school and I was doing miserably. I just received my results for my Western Civ test and had another “C.” I knew the material but I just froze on the test. Sheri, my roommate got another “A.” “I feel so dumb.” I told her. “You are very smart. I can tell by the questions you ask in class. Also, your homework is perfect. I think you are worrying about nothing.” Sheri said. “Then why do I do so badly on my test? Why can’t I get an A like you?” I cried. “I don’t know maybe you try to hard. Maybe you need to relax more?” Sheri said as she sat down next to me. “Relax? You mean party like you and not study?” I asked. “Well that could help, but maybe you need to relax before the test. You know go for a run in the morning or something.” Sheri said. “You don’t go for a run. You just take a long shower. Maybe just a long shower is all I need to do.” I told her. “Well that could help, but for me it is what I am doing not the shower.” Sheri said. With a puzzle look on my face, I asked her “What do you mean? If you are not showering what are you doing?” “Well you know?’ Sheri replied. “No I don’t know?” I said. “You know, taking care of business?” Sheri said with a little smile. Again, I did not know what she was talking about. “Business?” I questioned. “Do I have to spell it out for you? I was jillin. You know masturbating.” Sheri blurted out. I was kind of shocked. I mean I was eighteen and knew that some people did that sort of stuff. But those were bad people, dirty, nasty people. I though. “You mean you touch yourself, down there?” I asked. “Well yea. I find a good cum in the morning help take the edge off things. Don’t you do it every now and then?” Sheri asked. “No I don’t that is dirty.” I told her. “It is not dirty. Your fingers do get a little sticky if you do it right.” Sheri said with a giggle. “I would offer to show you but you probably know how to do it yourself.” Looking away from Sheri so I did not make I contact. I told her. “No I don’t. I have never done that. I was told that it was bad and to never touch yourself.” “Well the boys you have been with probably did things that made you feel good, right.” Sheri questioned. Again, without making eye contact I answered. “I have only been on two dates and all we did was kiss goodnight.” I told her. “You mean you are a complete virgin? Never had an orgasm? Never been touched? Never been fucked?” Sheri said in amazement. I started to cry. Sheri was making me feel so much like a failure “I am sorry I did not mean to make fun of you.” Sheri said as she tried to comfort me. “I will tell you what I will help you out. We have the whole weekend and I am here for you. I will be your own personal sex teacher. Any questions you have, any advice you need, I will be right here.” “You would do this for me?” I said feeling like she cared for me. “I will even let you use my vibrators and dildo.” She said. “Your what?” I questioned. Sheri got up from my bed and walked over to her dresser. Taking a box from her drawer, she came back to me in my bed. Opening the box, she pulled out this long rubber pink think. “This is a dildo. You insert it into your pussy and pretend you are being fucked. It feels pretty good.” Reaching in the box, she pulled out another object. “This is a vibrator. You put it on your clit for a mind blowing orgasm.” She said. “All of this seems strange. Where did you get them?” I asked. As Sheri handed me the dildo. “I got some of my toys on line and some at the Adult Book store in Hollywood.” Sheri said. “Will you show me how they work?” I asked. “Sure, as I said I will be you personal sex teacher this weekend.” Sheri told me as she leaned over and gave me a big hug. “Now to begin with I want you to get comfortable. I want you to take off all of your clothes and but on my robe. This way you can have complete access to your body. Also, I have some study material for you to look at. To help you find what turns you on.” Sheri said. “Study material?” I questioned. “Porn! Internet porn.” Sheri said. Sheri walked over to her computer and turned it on. “I have some websites I want you to look through. I also have some movies I want you to watch. There is probably enough to keep you busy for about two hours. I want you to look at everything I have in my bookmark and all the movies in my educational folder. Some of the stuff is single girls, girl on girl, boy on girl and even some men doing other men. Look through all of it and when I get back we will go to the next step.” Sheri said as she walked towards the door. “Where are you going?” I asked. “I was going to get some things and some Chinese food. This way you can be alone to explore. It starts with masturbation and that is something you can do for yourself. I think with the educational material and the toys you will figure it out.” Sheri said. As Sheri walked to the door, I rolled of the bed. “Sheri.” I said. “Thank you.” “I am glad to help this will be fun.” Sheri said as she walked out of the door. I walked over to the window and closed the curtains so I could have a little bit of privacy. Being naked was something that I did only when I showered. I felt somewhat strange stripping but at lease, I was alone. I removed everything as Sheri requested and placed my clothes neatly in a pile next to my dresser. As I walked across the room to get Sheri’s robe I noticed my naked form in the mirror. I stopped to take a look, something I never really did. I have seen myself in the mirror before but I never looked closely at my breast. Never really examined my breast. Never thinking how my nipples where kind of puffy. Like little cones. I wore a bra size of 32 B but there were moor to breast then just the size. I then looked down at my pubic hair and noticed the triangle shape it made pointing to my genitals, my vulva. Or as Sheri called it, my pussy. I than thought of other words I herd it called in different romance novels. My sex, my quim, my cunt, my love canal, and all terms for what I called “Down there.” I walked over and picked up Sheri’s robe. It felt warm and soft against my skin. I no longer felt naked but as Sheri pointed out, I still could access my body. As I sat down in front of Sheri’s computer, she had left the first website she wanted me to look at. It was called “Toying Teens.” As you can imagine it was pictures of young girls, well girls my age. They were naked and holding sex toys, like Sheri’s dildo. They were inserting them into their private parts. Some of these toys look very big and all the girls had big smiles, so I guess they liked it. Most of the girls had no pubic hair. I did not know if this was so you could see all of the pussy or was it to give them a younger look. A couple of the girls had puffy nipples like mine. Some had big erect nipples. I was imagining what it would feel like to have that big dildo inserted into my pussy. Along with the pictures, there was a link to a movie. It was only 30 seconds long and had this small girl inserting this huge black dildo into her pussy. It made me think that if she could insert that into her pussy. I should be able to do it too. The next website I went to was called coed Lesbos. It was pictures and movies of two and sometimes three girls together. They were kissing not only on the lips but also on their private parts. The girls were licking and putting their fingers into each other. Like in the other website, they also were using dildos and also a section called “Strap on Fuckers” The girls had strapped the dildo around their waist and were fucking the other girl. It was like having sex with a man but it was a fake penis. The girls were in different positions. Some had their legs spread laying on their backs and others where on their knees and the girl was behind them. I liked the close up pictures showing the dildo just barley inserted and then more and more until the two pussies were touching. I then went onto a page called cowboys and it was men together with other men. These guys had big erections. It looked kind of funny seeing a man with a penis inside his butt and him having an erection. It looked like the one guy had gone all the way through him and his penis came out the other end. I had never thought about what it would feel like to be fucked in the butt. At this point, I decided to look at some of the movies Sheri told me about in her educational folder. The first on was with a boy and a girl. It was in a foreign language but you can tell from the action what was happening. The girl was sitting on the edge of the bed and the boy was between her legs kissing her private parts. He was licking her with his tongue as he moved his finger in and out of her pussy. After a few minutes, he stood up and you could see his erected penis. The girl then started to suck on it and I could see it get even bigger. He then pushed her back and lifted her legs. Like most of the girls her privates had been shaved. I watched as a close up showed him trying to insert his penis into her. The camera cut to her face as she was biting her lip and then back to a close up of her pussy. He got a little more into her and you could here her yelps. He pulled out a little and pushed back in. You could see from her body movement that this was causing some discomfort. Again, he pulled out and pushed back in but this time he rammed her hard. The look on her face said it all. She must have been a virgin and this was her first time. He pulled his penis all the way out and you could see drops of blood. Then he put it back in her and proceeded to fuck her. This movie was about ten minutes long. I noticed my hand was between my legs rubbing my private part. I don’t know if it was because I liked what I was seeing or was it because I could feel her pain. I then clicked on another movie that had just one girl by herself. I watched her as she had this small vibrator that she was touching herself with. I went over and got the small vibrator and dildo out of Sheri’s box and did the same. It felt so nice on my nipple. I could feel the nipple get hard, just like when I am cold. But I felt this warmth running through my body. I moved the vibrator down to between my legs like the girl in the video. I must have hit the wrong spot because I had this shock run through my body. I dropped the vibrator because of the unexpected. Feeling. I bent over and picked up the small tool from the floor. I noticed the girl now was inserting the rubber dildo into her pussy, so I thought I should do the same. I put the head of this rubber object between the lips to my virgin entrance. Unlike the girl in the movie, it did not slide in as easily. I stood up, placed the dildo on the chair, and then lowered myself on to it, letting my body weight do the work. It went in further until I hit some resistance. This must be my hymen I said to myself, my maiden head, my cherry, my virginity. I lifted up some and came down hard. This time I shot passed the resistance and had completely penetrated myself. I had completely engulfed the dildo and the pain was unbelievable. My legs slammed shut as I withered in the chair. I wanted to pull the object out but that would mean opening my legs. I felt it was best to not move and wait for the pain to subside. The girl on the video was now fucking herself with the dildo while rubbing her clit with the small vibrator. I grabbed the small vibrator and turn the speed down to low. Not wanting to have the same shock as before. This time there was no shock, this time when the vibrator touched my clit it was a good feeling. I repositioned myself in the chair by placing both feet up on the computer desk and leaning back in the chair. This position change caused the dildo to slide a little bit. I now had about two inches sticking out that I could grab a hold of. Holding the vibrator on my clit I gently pulled the dildo out. I could feel the cool air rushing into my hot pussy. I decided to put the toy back in plugging my hole. Unlike the first time, this time there was no pain but this time it was pleasurable. With my legs spread wide I begin to imitate the girl in the video. Pulling and pushing the dildo in and out of my cunt, while rubbing my clit with the vibrator. I was feeling pleasure that I had never felt before. Faster and faster, I moved the dildo. I then changed the speed of the vibrator to high. My heart began to beat faster and my breathing became harder as if I was running a race. My head began to spin as a wave of pleasure rushed over me. I did not know exactly what was happening. This must be an orgasm that I had read about so many times in my romance novels. My one hand kept slamming the dildo harder and faster into my wetness. I could hear the squishing sound coming from my once virgin pussy. I could feel wetness dripping down my butt. My body began to tremble and every muscle in my body started to spasm. My toes curled as I shut my legs tight around my hands, keeping the dildo deep inside of me and the vibrator pressed hard against my clit. I felt like my body was exploding into a million little pieces. The spasms begin to reside and every muscle in my body began to relax. I was now in a state I never felt. Such a relaxed feeling. It was like I was on a big soft bed or a cloud floating in mid air. My legs gently fell apart releasing the hold on my hands. The small vibrator slipped from my hand rolling down my belly and then falling to the floor. I pulled the dildo slowly out of my well-satisfied pussy. I held it up seeing drops of moisture dripping from the tip. The drops feel softly onto my belly. As my focus came clearer, I noticed the drops were red in colored. Sitting up in the chair, I examined the dildo. It had blood on it. I must have ruptured my hymen. I thought to myself. All of the terms I heard came to mind, pooping my cherry, taking my maidenhead, losing my virginity. I slid a finger into my pussy and did a little inspection. It was a little sore but it should be fine. I got out of the chair and went into the bathroom to get a towel to clean up my mess. “How is it going? I see you are using my toys without me?’ Sheri said. “I made a little mess on your chair.” I told her. “I can see that. But more importantly how does it feel? She said with a trace of a smile. “I feel great.” I told her. “Do you feel stressed? More importantly do you think you could ace an exam?” Sheri asked. With a big smile walked over to her and gave her a big hug. “Yes I could ace an exam.” I told her. Now part of my study routine is playtime. With Sheri’s help and the Internet as a resource for “Educational” material, I found many new ways to pleasure myself. I think vibrators should be standard issue for all incoming freshmen in college.

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